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23 Best Things to Do in Chicago

By Nicole Schnitzler

Home to 77 neighborhoods, a robust lineup of festivals, a sprawling waterfront, and charming parks and walkways throughout, Chicago packs in something for every one of its locals. Add to that list award-winning theaters, iconic architecture, and a dynamic dining scene, and you’re looking at a world-class destination, too—smack dab in America’s heartland. The city’s draws only continue to grow, thanks to arrivals in everything from music venues to Michelin-starred restaurants—and the town’s hospitality remains strong, invested in helping others to enjoy those experiences across the board. From an education in the arts to an entirely outdoors itinerary (and plenty of easy-to-elegant noshes along the way), here are some of the best things to do in Chicago now.

Read our complete Chicago travel guide here.

This gallery has been updated with new information since its original publish date.

Garfield Park Conservatory Arrow

Step into the humid, glass-enclosed domes of Garfield Park where the air is clean thanks to thousands of jewel-toned plant specimens filtering toxins throughout. The space is fashionably untamed across its verdant showcase of flora from wet and dry environments, and those between. Spread across twelve acres, there's abundance year-round, from the colorful spring flower show to permanent indoor exhibits and holiday displays. Plant and garden enthusiasts should make the conservatory—easily accessed by Green Line—one of their stops.

Pizza City USA Arrow

In writing his book Pizza City USA , James Beard Award-winning food reporter Steve Dolinsky had organized the city into 10 different styles of pizza, quickly understanding Chicago’s wide array of pie styles. That research led him to start a tour showcasing that range, offering him and a team of “doughcents” a chance to tout Chicago’s diverse pizza scene to visitors and locals alike. There are four different kinds of tours, each exploring 3-4 styles of pizza. A walking tour Friday nights (downtown), a bus tour (various neighborhoods), and a walking tour (West Loop) on Saturdays, and a walking tour on Sundays (Bucktown/Wicker Park). Though the venues vary by tour, you can expect stops at favorites like Labriola (deep pan), My Pi (deep-dish), Robert’s (artisan), Paulie Gee’s Logan Square (Detroit-style), Eataly, and Bar Cargo (Roman). Get ready to grow your pizza IQ—in addition to discussing the range of pie styles, the team shares plenty of ‘za terminology and local history.

Urban Kayaks Arrow

Kayaking on the Chicago River or lake front is one way to shake up your perspective while visiting. Urban Kayaks offers tours along either. Move through the pulsing heart of the city on the river or travel Lake Michigan and circle Museum Campus (featuring the Field Museum , Adler Planetarium , Shedd Aquarium and Soldier Field). A night tour on the river boasts views of the glowing Merchandise Mart, which is showered in rotating, digital art displays projected onto the building. A one and a half hour skyline paddle in Lake Michigan gives you all the tourist sites without the foot traffic and crowds, showing you Grant Park and Navy Pier on a route few tourists trek.

The Salt Shed Arrow

The team responsible for some of Chicago’s best restaurants and concert halls is behind this hugely popular newcomer, housed within the iconic Morton Salt building on the North Branch of the Chicago River. The indoor-outdoor space made a soft debut last summer and continues those rollouts this year, with indoor shows this past winter and a full lineup this summer (including acts like First Aid Kit, Pretty Lights, Caamp, and Tash Sultana). Multi-level ticketing tiers help guests in selecting their vantage point for shows. Even if you don’t have prime sightlines every time (now considered the largest independent concert venue in Chicago, the space has a capacity of 5,000 for outdoor shows and 3,500 for indoors), you’re still in luck: They feature a state-of-the-art sound system by L-Acoustics. The venue also features a solid lineup of local food options, including Pizza Friendly Pizza and Café Tola. Find them in the outdoor Fairgrounds space (perfect for grabbing a bite pre-show).

Alex Erdekian

CNT Editors

Jesse Ashlock

Charlie Hobbs

The Morton Arboretum Arrow

Located about 30 minutes west of downtown Chicago, the Morton Arboretum feels like a world away. It's a pastoral escape that feeds the mind and heart. Art installations on site are rotated seasonally, several of them are dedicated to the natural sciences, such as the living exhibit dedicated to tree growth. 'Human+Nature' is the current installation here, showcasing the work of acclaimed sculptor Daniel Popper. Five pieces are currently on display in various locations across the arboretum's 1,700 acres, making this Popper's largest exhibition to date anywhere in the world. Open from 7:00 a.m. to sunset, daily—it's a relative bargain at $16 a ticket. With a maze garden and over 16 miles of hiking trail, this is the ideal urban getaway for outdoorsy sorts looking to decompress.

Wrigley Field Arrow

Iconic Wrigley Field is arguably one of Chicago's most storied landmarks, with millions of baseball fans flocking to the stadium just to get a photo in front of the iconic Wrigley Field Marquee (whether they’re rooting for the Cubs or not). The stadium anchors the Wrigleyville neighborhood, which has experienced a boon in development. A new outdoor plaza, luxury hotels, and an influx of restaurants/bars have boosted the area's cultural cachet, so it's worth hanging around before or after your stop at the stadium.

Museum of Contemporary Art, Chicago Arrow

The MCA is one of the city’s museums that’s in a near constant state of transition. With its relatively small permanent collection, it relies on special shows—from large scale installations to video, fashion, music, photography, and more—that showcase just as many rising local talents and underground, avant-garde renegades as recognizable names. Past exhibits include David Bowie Is, Takashi Murakami: The Octopus Eats Its Own Leg, and Virgil Abloh: Figures of Speech.   It also has one of the best gift shops (ever) and is home to Marisol, where chef Jason Hammel puts forth thoughtful, seasonal cuisine. Come summer, visit for their “Tuesday on the Terrace” music series, along with 21 Minus, an annual festival celebrating the next generation of artists.

Midway Plaisance Arrow

Known simply as the Midway, this mile-long natural stretch on the South Side connects the east end's Washington Park to Jackson Park on the west. Once the site of amusements during the 1893 Columbian World's Exposition (AKA World's Fair), the Midway is flanked by Hyde Park's noted gothic architecture, particularly the University of Chicago campus, and tree-lined boulevards, as well as outfitted with an ice skating rink and other facilities to keep folks visiting year-round.

Lincoln Park Zoo Arrow

Located in the heart of Chicago's Lincoln Park, this zoo offers free, family-friendly entertainment year-round including the festive Zoolights around the holidays (reservations are required for all visits though). The sprawling grounds are seamlessly woven into the park’s landscape, balancing open, natural spaces and numerous animal exhibits. If you skip the pricey concessions (but maybe spring for a paddle boat ride), Lincoln Park Zoo is a great option to keep all ages occupied while staying on a budget. Visit the animals, take a spin on the AT&T Endangered Species Carousel or the Lionel Train Adventure, and enjoy family-friendly dining options, such as Bird’s Eye Bar & Grill or the Patio at Café Brauer. 

Art Institute of Chicago Arrow

If you're coming to Chicago for culture, you're hitting the Art Institute first. It is the city's grandest museum, a Beaux Arts gem flanked by two bronze lions that are as much a symbol of the city as the Willis Tower and it has as fine an impressionist collection as you'll find anywhere. While you're there, plan to take a stroll through Millennium Park next door.

Bloomingdale Trail (The 606) Arrow

Chicago's answer to New York's High Line , the Bloomingdale Trail—a.k.a. The 606—is a nearly three-mile, elevated greenway running west and east on the city’s North Side. Unlike its NYC counterpart, the trails are wide enough to accommodate active patrons running, walking and cycling without running off more casual strollers, the formerly abandoned rail line is also lined with public art installations and gardens. During fairer weather, the trail also hosts various free events for families with young children.

3 Arts Club Cafe Arrow

Today there are more than 15 RH restaurants across the nation, but Chicago’s 3 Arts Club Café, which opened in 2015, was the first. Guests will discover it within Restoration Hardware’s 70,000-square-foot design gallery, which formerly functioned as the Three Arts Club, a residence built in 1914 for young women studying music, drama and the visual arts. Today, that space has been royally reimagined in the hands of RH, turning the six-story building into a lavishly outfitted labyrinth featuring its myriad décor whimsies (from the brand’s Design Atelier line to its children’s collections). Come here with friends or a special plus one, and arrive early—you'll want to factor in time for grabbing a coupe and perusing the historic property as you await your table.

Humboldt Park Arrow

One of Chicago's prettiest parks, this nearly 200-acre green space is located within the larger neighborhood of Humboldt Park (both are named for German naturalist Alexander von Humboldt). It's home to several statues—including one of its namesake, and two bison that were placed there during the 1893 World's Fair—as well as the National Museum of Puerto Rican Arts & Culture, located in the park's former stables. It's easy to drop in if you're headed down the 606 trail, but the park is big enough that it could take more than half a day to do all of it, so it's best if you're not in a rush.

The Second City Arrow

Tina Fey, Bill Murray, and Chris Farley all grew out of the scene at Second City and it continues to nurture some of the country's best comedy talent. Over three stages and four intimate studio theaters, there's plenty to see. The Mainstage show, featuring that season's top billed act, features long-form improv sketch, and is often packed on marquee nights. The same can be said for the e.t.c. Theater, which showcases up-and-comers, and the Up Comedy Club, for stand-up comic acts. The shows tend to be full, and ticketed for general admission, so come early to snag a prime seat. (Pro-tip: Avoid front row if you don't want to crane your neck all night.)

Chicago Lakefront Trail Arrow

The 18-mile long trail hugs the coast of Lake Michigan, offering almost all manner of activity along the shore. From sandy beaches and sprawling parks, to some of the best views of the Chicago skyline, the Lakefront Path is one of the city's great public treasures, enjoyed by visitors and locals alike. Runners and cyclists love the width and ease of use of the trail, while intramural type teams make use of the many open spaces found up and down the path. If you don't want to run around, there’s plenty of room to just sit and people watch, as well as check out a number of art installations that pop up throughout the year.

Chicago Electric Boat Company Arrow

Auditorium Theatre Arrow

Inspired to build a theater that would benefit the city and serve as the world’s largest and most ornate building, Chicago businessman Ferdinand Wythe Peck began plans for the Auditorium Theatre and debuted the venue in 1889. Since then, the theater has been the site of major historical events and performances and earned impressive titles along the way (including a National Historic Landmark designation). Keep an eye on this season's calendar for events with Tom Hanks, The National, and Loreena McKennitt, among others. Anyone seeking a dose of the arts in elevated, historic environs will do well by a visit here. Gather friends for a speaker event or concert, or make it a date night.

Green Mill Arrow

Do not come here expecting fancy drinks—or anything fancy, really. This is living, breathing history. And it's a rocking good time. The Green Mill is a warm and inviting throwback to a bygone era. There’s live jazz, cheap drinks, and loads of local history (Al Capone used to have a booth reserved here during Prohibition); what's not to love? Bar eats are not on the menu here. Bring your own potato chips if you think you'll need a snack (no one will judge you). The craft beer list has expanded commendably over the past few years. So grab yourself a cold one or a whiskey soda and see where the night takes you.

Chicago Architecture Foundation River Cruise Arrow

Run by the Chicago Architecture Center, the Architecture River Tour is one of the most polished operations in town ( and a wonderful alternative to some of the cheesier tours ). Taking place on a barge in spring, summer, and fairer fall weather, the cruise explores Chicago's beginnings from various branches of the Chicago River—offering both day and evening tours. While groups are typically large, the Architecture Center-trained docent speaks via loudspeaker, audible from throughout the boat. (Pro-tip: Head straight upstairs when you board and snag a seat in the rear for optimal views.) In 90 minutes, you'll get to know 50 buildings along the Chicago River, hear secrets about a map of the river's topography hidden in plain sight, and learn about the only skyscraper in the skyline designed by an award-winning female architect.

Promontory Point Arrow

This man-made peninsula in Burnham Park has become a favorite gathering and photo shoot spot for locals due to its manicured landscape and rock formations along the lakefront. Our plan of attack here is to have a picnic at the point, then walk among a number of public art works edging the surrounding park. Some of the most interesting  public art installations and gathering spaces, such as Sounding Bronzeville and La Ronda Parakata, are actually within the Burnham Wildlife Corridor, which is composed of the Burnham Centennial Prairie, Burnham Nature Sanctuary, and McCormick Bird Sanctuary.

Chicago Symphony Orchestra at Symphony Center Arrow

Intuit: The Center for Intuitive and Outsider Art Arrow

Among the only museums in the world dedicated wholly to outsider art, Intuit is an impressive shrine to self-taught creators across all forms of media. Beyond an unassuming, brick facade, you’ll brush up against a concise-yet-vibrant collection of paintings, sculptures and assorted ephemera. The collected work draws you in with an air of unconventional audacity. This is a whimsical environment with an industrial edge. Exhibits are spread out with ample room for wandering and gazing at your leisure. The museum is curated by passionate docents who are committed to the cause of promoting the artistic output of marginalized creatives.

Chicago Botanic Garden Arrow

The Chicago Botanic Garden, a 385-acre living plant museum, features 28 distinct gardens and four natural areas. Those figures are impressive enough to draw more than one million visitors annually, making it one of the most frequented botanical gardens in the United States . Inside the gates, the Garden’s living collections feature more than 2.8 million plants from around the world that grow well in the Chicago area and are adapted to Midwest climate and soils. Expect to see a lush array of trees, shrubs, vines, and tropical plants, among other varieties.

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40 Best Things to Do in Chicago, From Iconic Sights to Can't-miss Museums

Planning a trip to the Windy City? Here are 40 of the best things to do in Chicago.

Meena Thiruvengadam is a lifelong traveler and veteran journalist who has visited more than 50 countries across six continents. Her writing has appeared in The Wall Street Journal , Departures , TripSavvy , and other publications.

Chicago may not be the city that never sleeps, but there is surely more to do here than you'll have time for. Whether it's world-class art, a cultural experience, or sports you seek, you'll find it in the Windy City. Here are 40 of the best things to do in Chicago.

Valerie de Leon/Travel + Leisure

See masterpieces at the Art Institute of Chicago.

This downtown museum isn't just an architectural gem, it's one of the best art museums in the United States. It's home to famous pieces, including Edward Hopper's "Nighthawks" and Grant Wood's "American Gothic," as well as the largest collection of works by Claude Monet outside of Paris.

Take an architecture river cruise.

With several buildings designed by greats like Frank Lloyd Wright and Ludwig Mies van der Rohe, Chicago is an architecture nerd's paradise. And one of the best ways to appreciate the cityscape is from the river. While there are dozens of cruise operators, Chicago's First Lady Cruises stands out for its 90-minute architecture cruise guided by experts from the Chicago Architecture Center.

Tour a submarine at the Museum of Science and Industry.

The largest science center in the Western Hemisphere, this Hyde Park museum is a great place to spend a cold or rainy day. The permanent exhibits focusing on science, technology, and nature are extensive but it's worth upgrading your ticket to include a tour of the only German submarine in the U.S. Check the schedule for special exhibitions, which can also be a treat.

Step back in time at the Chicago History Museum.

Chicago is where Al Capone once played and where Playboy was born. It's a city full of stories to tell, and there's no better place to discover them than one of the city's oldest cultural institutions, the Chicago History Museum .

Meet a dinosaur at the Field Museum of Natural History.

The Field Museum is one of the largest natural history museums in the world, and its permanent collection includes a number of fossils and the remains of Sue, the Tyrannosaurus Rex. Sue is estimated to be 67 million years old and made her debut at the museum in 2000.

Have a few laughs at a comedy club.

Several famous comedians (Tina Fey, Chris Farley, and Jim Belushi, to name a few) got their start at Chicago's well-known comedy clubs, including The Second City . New stages have since popped up, like Laugh Factory and The Revival . Who knows? You might see the next rising star of Saturday Night Live before they hit it big.

Listen to live music.

Chicago is a live music heaven, with venues that host performers of all genres throughout the year. In the mood for classical? Experience the talents of the Chicago Symphony Orchestra . Craving jazz? Head to the historic Green Mill jazz club. The city is also home to several music festivals, including Lollapalooza , Riot Fest , and world-famous blues and jazz festivals.

Go to the beach.

Believe it or not, Chicago is a beach town during the summer. Oak Street and North Avenue beaches are two sandy beaches along Lake Michigan that are close to downtown and will allow you to bask under both the sunshine and the shadows of the city's skyscrapers.

Brave the Skydeck of the Willis Tower.

Formerly known as the Sears Tower, this towering giant was once the world's largest skyscraper. That may have changed, but its expansive observation deck on the 103rd floor still offers some of the best views of the city. Those looking for a thrill can step onto The Ledge, a glass balcony extending out 4.3 feet from the building.

Stop at 875 North Michigan Avenue.

This 100-story building (formerly known as the John Hancock Center) may not be as well known as the Willis Tower, but it's another place for epic city views. There are restaurants, bars, the 360 Chicago observation deck , and occasional events like yoga classes.

Enjoy the free attractions in Millennium Park.

Located in downtown Chicago, Millennium Park is one of the city's largest green spaces. It's easy to spend a few hours here, especially since most of its attractions are free. The Frank Gehry-designed Jay Pritzker Pavilion hosts free concerts and other public events every summer. On a hot day, many cool off in the whimsical Crown Fountain , an interactive public artwork designed by Catalan artist Jaume Plensa.

Take a photo with "The Bean."

Chicago is full of public art , but this reflective sculpture by artist Anish Kapoor is one of the most recognizable pieces. While the Millennium Park attraction is officially titled "Cloud Gate," most visitors and locals affectionately call it "The Bean."

Admire Buckingham Fountain.

If you've ever watched Married with Children , this fountain set in sprawling Grant Park at the edge of Lake Michigan is one you'll definitely recognize. Opened to the public in 1927, it's one of the largest fountains in the world.

Take an architecture walking tour.

There are few better ways to experience Chicago's world-famous architecture than on foot. The Chicago Architecture Center offers several different walking tours, including some focusing on the skyscrapers that tower high above the city's streets.

See the animals at Lincoln Park Zoo.

This 35-acre zoo , founded in 1868, is one of the oldest zoos in North America. It's free to visit and hosts an annual holiday lights show .

Go to the theater.

Broadway isn't the only place to catch a show. Chicago has more than 200 theaters, including the well-known James M. Nederlander Theatre and Cadillac Palace Theatre in the Theater District. It's also worthwhile to check out the city's independent stages, such as the Tony Award-winning Chicago Shakespeare Theater at Navy Pier or the innovative Steppenwolf Theatre in Lincoln Park.

Shop the Magnificent Mile.

If you're looking to do some serious damage with your credit cards, look no further than the stretch of Michigan Avenue known as the Magnificent Mile . You'll find a mix of high-end designer stores, sprawling department stores, and more affordable retailers like Marshalls.

Tour a Frank Lloyd Wright house.

If you're a fan of architect Frank Lloyd Wright's work, head to the University of Chicago campus in Hyde Park, where you'll find the Frederick C. Robie House . The house, built in the early 1900s as a single-family home, is a fine example of Prairie School design and is among nearly two dozen homes in the area designed by the famous architect.

See the "Home Alone" house.

You'll need a car to get to this house in the Chicago suburb of Winnetka, but if you grew up on "Home Alone," it'll be worth the drive. You'll recognize it the second you pull up, but remember it's a private residence, so you'll have to appreciate it from the outside.

Go ice skating.

Chicago may get cold in the winter, but the joy of ice skating almost makes you forget about the freezing temperatures. From November to March, the Maggie Daley Ice Skating Ribbon in Grant Park and the McCormick Tribune Ice Rink in Millennium Park are popular spots for Chicagoans and visitors.

Catch a Cubs game at Wrigley Field.

Wrigley Field is one of the most charming stadiums in baseball. It's home to the former World Champion Chicago Cubs, and if you don't happen to be traveling during baseball season, you can still take a tour.

Learn about the history of Soldier Field.

The nearly 100-year-old Soldier Field is home of the NFL's Chicago Bears. Even if you're not into football, you might recognize it from the Clint Eastwood movie "Flags of Our Fathers" or the television show Chicago Fire . The stadium offers behind-the-scenes tours that pass through the locker rooms, interview room, skyline suite, and other areas.

Ride the Ferris wheel at Navy Pier.

If you're looking for a day of family fun, head to Navy Pier in downtown Chicago. The long pier features rides, games, restaurants, public artwork, and other attractions. Be sure to ride the Centennial Wheel for a truly spectacular view of Lake Michigan.

Take a walk in Oz Park.

There may not be a yellow brick road leading to Oz in Chicago, but there is a park that pays homage to the "Wizard of Oz," which author Frank Baum wrote while living in Chicago. Oz Park on the city's north side features sculptures of all your favorites, including Dorothy, Toto, and the Tin Man.

Explore a Chicago neighborhood.

Chicago is a city of neighborhoods — 77 of them, to be exact. Wicker Park, Bucktown, and Logan Square are worth exploring on the city's north side. On the south side, consider Pilsen and Chinatown. Architecture buffs are sure to appreciate the historical gems they'll find in Old Town.

Visit the DuSable Black History Museum and Education Center.

This Smithsonian-affiliated museum celebrates Black culture and pays homage to Jean Baptiste Point du Sable, the first permanent settler of Chicago. The museum holds more than 15,000 works, including paintings, sculptures, and historical memorabilia, such as the former desk of investigative journalist Ida B. Wells.

Eat your heart out.

Chicago is a foodie paradise that offers something for every palate and every budget. You'll find everything from hot dog joints like Jimmy's Red Hots to Michelin-starred restaurants like Alinea to deep-dish pizza places like Pequod's . Be sure to pack your stretchy pants, and remember, Chicagoans don't ask for ketchup on their hot dogs.

Visit the National Museum of Mexican Art.

This museum in the Pilsen neighborhood is an ideal place to immerse yourself in Mexican art and culture within Chicago's city limits. It's one of few major museums in the U.S. dedicated to showcasing Mexican, Latino, and Chicano art and culture.

Kayak along the Chicago River.

If you're craving an active adventure in the city, you can't go wrong with kayaking on the Chicago River. Urban Kayaks organizes a range of guided excursions, including tours at sunset and during the weekly Navy Pier fireworks show.

Check out the Museum of Contemporary Art Chicago.

Chicago has no shortage of museums, but when it comes to boundary-pushing exhibitions, the Museum of Contemporary Art Chicago (MCA) is second to none. The MCA's permanent collection includes more than 2,000 artworks from the 1920s to the present day, while rotating exhibits, performances, and talks are held throughout the year.

Hop between breweries.

Home to more than 160 breweries, Chicago is often dubbed the craft beer capital of the U.S. From cozy brewpubs to bustling beer gardens, there's something for everyone. Several production facilities, including Goose Island , Revolution Brewing , Lagunitas Brewing Company , and Dovetail Brewing , are also open for tours and tastings.

Stargaze at the Adler Planetarium.

You don't need to leave Chicago to see the stars – just head to the Adler Planetarium on Northerly Island. America's oldest planetarium is a destination for sky shows, exhibits, and special events. As a bonus, it stays open until 10 p.m. on Wednesdays.

Bike along the Lakefront Trail.

Chicago’s Lakefront Trail is a scenic 18-mile paved path along Lake Michigan between Ardmore Street on the north side and 71st Street on the south side. For a fun outing, rent one of the Divvy Bikes and explore it from top to bottom — including a break at one of the beaches along the way.

Celebrate St. Patrick’s Day.

Chicago's Irish pride beams as bright as the green dye in the river every March. Highlights include the annual Chicago St. Patrick’s Day Parade , river cruises, and food and drink specials at neighborhood pubs. If you're lucky (or a good planner), your trip might coincide with some of the festivities.

Stroll along The 606.

The Bloomingdale Trail Park (The 606) is an elevated recreational trail built on an abandoned railway. Similar to New York's High Line, the 2.7-mile-long path is dotted with public art installations and scenic lookouts. Access points can be found in four of the city's trendiest neighborhoods – Wicker Park, Bucktown, Logan Square, and Humboldt Park – so you can easily hop on or off.

Marvel at art among trees at the Morton Arboretum.

The Morton Arboretum was established in 1922 as a "great outdoor museum" by Joy Morton, founder of the Morton Salt Company. And with more than 1,700 acres and 22,000 plants, it certainly lives up to its mission. The park features rotating large-scale sculpture exhibitions and wellness events like forest therapy and yoga classes, making it well worth the journey 25 miles west of Chicago.

Spend an evening at the American Writers Museum.

Located in the heart of downtown Chicago, the American Writers Museum celebrates the work of historical and present-day writers, from poets to comics to novelists. The museum regularly hosts concerts and special events, including Get Lit museum nights, which bring together bibliophiles for drinks, special tours, and activities on the second Tuesday of every month.

Stop and smell the flowers at the Garfield Park Conservatory.

Garfield Park Conservatory is one of the largest conservatories in the nation, with two acres of public greenhouse space and 10 acres of outdoor gardens. The West Side centerpiece opened in the early 1900s and continues to be a destination for lovers of landscape architecture. In addition to permanent display houses, the conservatory often hosts special exhibits and spring flower shows. 

Learn about the city's criminal history.

Joining a crime tour is a fascinating way to learn about the city's prohibition-era gangsters like Al Capone, Bugs Moran, and Hymie Weiss. Opt for the Gangsters and Ghosts Tour for a storytelling stroll around the Chicago Loop, or board a bus for the Untouchable Tours' Original Gangster Tour led by guides in character as 1920s mafia members.

Admire the skyline from a cruise on Lake Michigan.

While Chicago's river cruises get a lot of attention, sailing around Lake Michigan can be just as fun. Tall Ship Windy offers a variety of cruises aboard a 148-foot, traditional four-masted schooner, including pirate-themed tours and skyline sailings that make the most of the Windy City's namesake weather.

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Everything you need to know before visiting Chicago

Aug 15, 2023 • 8 min read

Use these top tips to help you make the most of your time in Chicago © Ryan McVay / Getty Images

I’ve lived in Chicago for more than 30 years, and these are the top tips I tell all of my visitors: take public transport, hit the neighborhoods and drink Malört at your peril.

Then you need to know about local sports culture, the ridiculous taxes and the ketchup rule… and that’s just for starters. I've gathered together all the top insider tips you need to ensure a smooth visit to the Windy City.

Plan on 3 to 5 days to visit

It’ll take you two to three days to see the highlights, like the Art Institute , Wrigley Field , Millennium Park and Willis Tower . Adding an extra couple of days to your visit allows you to move out of the center and into the neighborhoods , where Chicago’s true heart beats.

Pilsen and Logan Square welcome you with chowhound eats and vibrant street art. Bronzeville has galleries and soul food restaurants and Andersonville is a jazzy, cafe-laden LGBTQI+ hub. Hyde Park, Wicker Park and Humboldt Park are other troves of great restaurants and attractions.

Don’t drive, especially downtown

Driving in Chicago is no fun. Traffic snarls not only at rush hours but also most times in between. Road construction on the main highway through town has only added to the nightmare. What’s more, parking is hard to find and costs a fortune, particularly downtown near the sights – garages routinely charge around $45 per day. Ditch the car and use public transportation to spare yourself the annoyance.

Buy a Ventra Card for public transportation

It’s easy-peasy to make your way around Chicago on public transport – mainly the L trains, which run on both elevated and subway tracks. They’ll get you to most sights and neighborhoods into the wee hours. Buses pick up the slack in areas that the L misses.

To save time and money, buy a rechargeable Ventra Card to use on transit and add value as needed. Cards are available at any L station (including at the airports) and save around $0.75 per ride over disposable fare tickets. You can also download the Ventra app and buy a digital Ventra Card. The app has the bonus of providing L and bus times, too.

Whether using a plastic or digital card, simply tap it at the turnstile as you enter the L station or at the farebox as you get on the bus. If you’ll be riding three or more times per day, consider buying an unlimited ride day pass for additional savings.

Use the L to get to and from the airports

The aforementioned traffic is no joke. Taxis and ride-shares can take forever to get between the city and airports. Instead, use the L train. The Blue Line from O’Hare and Orange Line from Midway take 30 to 40 minutes and cost $3 to $5. Not only are travel times often quicker on the L, but it’s about 10 times cheaper than a cab.

Book museum and theater tickets in advance

Many museums, including the Art Institute , encourage tickets to be purchased online in advance from the museum’s website. A day or so prior should do it, unless there’s a blockbuster exhibit going on.

It’s also wise to book theater tickets beforehand, whether it’s for a world-class opera or booze-addled Shakespearean improv. A week ahead is usually plenty of time. Browse Hot Tix for same-week drama, comedy and performing arts tickets for half price.

Make restaurant reservations

Prepare to fork into platefuls of Michelin-starred comfort food and eat like royalty. Reservations are key, though, especially for weekend dining. Book through Tock , Open Table or Resy . A week or two in advance will work for most places, though hot spots such as Alinea and Girl & the Goat need to be reserved a couple of months out. Prime dining times are between 6pm and 8pm.

Pack a warm coat, but also a bathing suit

Chicago sits on the shore of vast Lake Michigan, which has a wild effect on the weather. It whips up heavy snow in winter and windy conditions year-round . Pack a warm coat, hat and sturdy shoes when visiting November through March. Even in summer, the temperature can drop fast, so bring a sweater when you head out for the day.

That’s not to say you shouldn’t also bring your bathing suit from June through August. The city has several beaches that beckon with sand and surf.

Where you stay depends on what you want to do

Downtown has loads of cool architectural hotels near the sights, but limited eating and drinking options after dark. Not ideal if you're looking to party but a good option if you're traveling with young kids.

Next door the Near North has hotels and evening action, but it’s pricey and a bit cookie-cutter. The West Loop, Lincoln Park, Lake View and Wicker Park all have abundant nightlife to keep you entertained into the wee hours. They’re not close to the main sights but are easy enough to access via the L. Book accommodations a month or two in advance, if possible.

Prepare for hefty taxes

A tax is levied on most goods and services in Chicago. It’s 17.4% for lodgings, 10.75-11.75% in restaurants and bars (it's higher the closer you are to downtown), and 10.25% for other items. The tax is typically not included in the price but added to the bill when you pay.

Cheer on the sports teams

Chicagoans are rabid sports fans – get to know the city's teams and you’ll make friends wherever you go in town.

Chicago’s two baseball teams inspire a diehard rivalry: the Cubs are the more moneyed North Side squad, while the White Sox are the blue-collar, working-class team on the South Side. Both have had great success in recent years. Then again, both have sucked in recent years, too! Usually, one team is up when the other is down.

The football-playing Bears ignite lots of fervor, but they’re typically not very good. They're followed by basketball's underachieving Bulls , hockey's try-hard Blackhawks , and soccer’s middling Fire .

Dress casual

Chicagoans dress informally. The apex of fashion for most men is a pair of khakis and a button-down shirt. Women's dress is similarly low-key, valuing comfort over high fashion. And don't worry about getting your best on for the evening. It's perfectly fine to wear jeans and casual clothes to dinner or the theater at night. No judgment here!

Never put ketchup on a hot dog

Weird but true: the red condiment does not go on local wieners. No one really knows why. One theory is that the famed Chicago-style hot dog – which is topped with mustard, sweet pickle relish, chopped onions, tomato slices, a dill pickle spear, sport peppers and celery salt – already has a perfect flavor balance. Adding ketchup is redundant and ruins the meaty harmony.

Grab a seat at the bar

Locals love to hang out in drinking establishments. Blame it on the long winter, when folks need to huddle together somewhere warm. Blame it on summer, when sunny days make beer gardens and sidewalk patios so splendid.

Beer is the drink of choice. No surprise given Chicago is home to more breweries than any other US city . Grab a seat in a neighborhood taproom, and you’ll be conversing about the Bears or the mayor in no time. You might even get offered a shot of Malört. It’s a local liquor famous for tasting awful . Downing one is a Chicago rite of passage.

Use the Pedway

Come wintertime, when the going gets tough and icy sleet knifes your face, head down to the Pedway . Chicago has a 40-block labyrinth of underground walkways, built in conjunction with the subway trains. The system isn’t entirely connected, and it’s confusing to figure out directions, but it’s also a dandy way to escape the elements. Look for "Pedway" signs above ground at points of entry.

Be courteous on the L

Let passengers get off the train before getting on yourself – wait beside the open door until everyone has departed. When you take the escalator in the stations, stand on the right side and walk on the left side.

Don’t smoke pot in public

Even though it’s legal to buy recreational marijuana throughout the city – at licensed dispensaries, cash only – you can only toke on private property. A backyard or balcony is fine, a car or cafe is not. Always check with the property owner to make sure they allow it.

As for cigarettes, you can’t smoke inside bars, restaurants and other public places, or within 15ft of the entrance.

Don’t let the headlines scare you away

Chicago has the unfortunate reputation of being the USA’s murder capital. While it’s true the city has the largest total number of homicides of any American municipality, it ranks much lower on the list when considered on a per capita basis .

Most of the violence is concentrated on the West and South Sides, where a handful of neighborhoods account for more than half of all shootings . These are communities where segregation and isolation have intensified inequality, and local gangs account for much of the bloodshed .

Overall, serious crime in Chicago has been dropping in recent years, according to city statistics. Still, it’s wise to take normal, big-city precautions, especially if solo at night. Many crimes involve cell phone theft, so be subtle when using yours. If driving, stay aware of your surroundings, as carjackings have been on the rise.

This article was first published Sep 16, 2021 and updated Aug 15, 2023.

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Chicago   Travel Guide

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Why Go To Chicago

"It is hopeless for the occasional visitor to try to keep up with Chicago – she outgrows his prophecies faster than he can make them," wrote Mark Twain in "Life on the Mississippi." Although Twain made up his mind about the Windy City before it even reached its 50th year, his impression of Chicago has proven long-lasting. America's third-largest city has been described in a myriad of ways throughout its lifetime. When Thomas Edison and Nikola Tesla were competing for the right to use their forms of electricity to illuminate the 1893 World's Columbian Exposition (also known as the Chicago World's Fair), Chicago was known as a city of industry. When Prohibition set in, notorious mobsters like Al Capone transformed Chicagoland into their own dangerous playground. And intense immigration surges throughout the 20th century brought a host of new identities to the Windy City, including Greek, Polish, Italian, Irish and Jewish.

Today, Chicago remains just as diverse, boasting a thriving arts scene, various shopping districts and a cornucopia of eateries. First-time Chi-Town visitors are sure to have their eyes to the sky for at least a day or two. Chicago's skyscrapers and public art are absolutely worth admiring: Tag along on a  Chicago Architecture River Cruise  or pass a few hours in  Millennium Park  and you'll find yourself spending lots of time looking upward. For a bird's-eye perspective, head to Willis Tower's  Skydeck Chicago  or the John Hancock Center's  360 CHICAGO Observation Deck . After, dive headfirst into all the city has to offer – from exceptional museums to a thriving sports culture and deep-dish pizza that takes delicious to whole new depths. If you need a little help navigating Chi-Town, consider signing up for one of the best Chicago tours .

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• # 3 in Best Food Cities in the U.S.
• # 3 in Best Weekend Getaways in the Midwest
• # 7 in Best Party Cities in the U.S.

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Best of Chicago

Best hotels in chicago.

• # 1 in The Langham, Chicago
• # 2 in The Peninsula Chicago
• # 3 in Four Seasons Hotel Chicago

Best Things to Do in Chicago

• # 1 in Millennium Park and Cloud Gate
• # 2 in Grant Park and Buckingham Fountain
• # 3 in Art Institute of Chicago

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Chicago Travel Tips

Best months to visit.

The best times to visit Chicago are April through May and between September and October, when the temperatures are warm, a variety of festivals take place and crowds are manageable. Summer marks Chicago's peak tourist and  festival season , with travelers from around the country hoping to take advantage of the warm weather and abundant activities. You'll find higher lodging rates during these seasons, but you'll also escape Chicago's notoriously bitter winters. Chicago experiences frigid temperatures from November to March, but if you can hack it, hotel and airfare deals are easy to find.

Weather in Chicago

Data sourced from the National Climatic Data Center

What You Need to Know

Winter is no walk in the park Winter temperatures in the teens and 20s are made worse by biting wind chills. Come prepared with a warm hat, a reliable pair of gloves, a thick coat and sturdy boots if you're visiting during this season.

You don't need wheels Forget the car: Chicago's extensive public transportation system is a much better (and easier) way to get around. A Segway tour is another fun way to sightsee without having to rely on your own two feet. The city also has a bike-share program called Divvy.

You've got a lot to see So schedule wisely. Group the things you want to do by neighborhood to avoid wasting time in transit.

Consider a tour For a local's perspective of the city, book a tour . Whether you're looking for a food tour, a boat tour  or a walking tour , you'll find a variety of experiences to choose from.

How to Save Money in Chicago

Bundle up  The weather outside may be frightful, but there are plenty of deals to be found during the winter months. Many  hotels slash their rates, and cheap flights are easy to come by.

Head north  Hotels in the Loop cater to business travelers staying on the company dime. For a more down-to-earth (and affordable) place to hang your hat, check out the bed-and-breakfasts in North Side neighborhoods like Lincoln Park and Lakeview.

Invest in an all-access pass  The  Chicago CityPASS  and the  Go Chicago Card  grant access to Chi-Town's most popular  attractions  for one set price. This will help you shave big bucks off your entertainment expenses.

Culture & Customs

Chicago boasts its fair share of fine restaurants , but don't miss your chance to sample the regional fare. Chicagoans strongly believe that their pizza and hot dogs are better than those in  New York City  – you may simply want to agree rather than spark a debate. And when you're ordering a beverage, remember that in Chicago soda is called "pop."

Residents of Chicago are also dedicated to their sports teams. You should have no trouble finding a fellow fan of "da Bears" or "da Cubs" (phrases made famous by "Saturday Night Live") at one of the many sports bars scattered throughout Wrigleyville.

If you prefer performing arts to sports,  The Reader  and  Time Out Chicago  can point you to musical and theatrical performances taking place around the city. And don't forget to check out one of the city's famous comedy shows, which are offered regularly through local comedy groups like  The Second City  and  UP Comedy Club .

What to Eat

Most people associate Chicago cuisine with three things: pizza, hot dogs and steak. They wouldn't be wrong. The Windy City has an ongoing rivalry with  New York City  over who can serve up the better slice – while New Yorkers prefer wide and flat, Chicagoans like their pizza with a deep crust that can carry loads of toppings. For hot dogs, New Yorkers like their hot dogs simple with potato buns and ketchup, mustard or relish, while Chicagoans enjoy their beef franks on a poppy seed bun with yellow mustard, chopped white onion, tomatoes, dill pickles, pickled peppers and a dash of celery salt.

Chicago is also known for its  steakhouses  – the Loop and the North Side are littered with fine dining establishments that serve prime cuts of beef. Some of the most reputed steakhouses include Joe's Seafood, Prime Steak & Stone Crab  just off The Magnificent Mile and  Bavette's Bar & Boeuf  in the River North area. Just be warned: A good steak doesn't come cheap in this town.

Another Chicago dish that's popular with locals, but not as well-known to tourists is the Italian beef sandwich. Created by Chicago's Italian immigrant community in the early 1900s, this seasoned roast beef sandwich soaked in meat drippings and topped with spicy giardiniera or sweet Italian peppers is found on many hot dog stand and restaurant menus. But, if you want to enjoy an authentic Italian beef sandwich, locals recommend visiting  Portillo's . Two locations – one on West Ontario Street in River North and another on West Taylor Street near the South Loop – are available in the downtown area.

If you're looking to save on dining (but don't want to survive on pizza, hot dogs and Italian beef sandwiches alone), move away from the downtown area into Chicago's more immigrant-dominated neighborhoods. Travel west for the hummus and tzatziki in Greektown, pasta in Little Italy or tacos in the Lower West Side. Or, head south of downtown to Chinatown for Asian specialties. If you're not sure what you're in the mood for, North Side neighborhoods like Streeterville, Lakeview and Lincoln Park boast eclectic restaurant scenes. Authentic Indian and Pakistani fare are also available west of the North Side's Rogers Park neighborhood along West Devon Avenue. Another great way to explore Chicago's wealth of culinary options is on a  food tour  or one of the best Chicago walking tours .

When you've got a hankering for a cold, crisp beer, consider touring one of the  city's top breweries . Or, head out for a night on the town to one of the  bars locals love , such as Cindy's rooftop bar or Jake Melnick's Corner Tap . And if you have time, locals say you should make reservations for brunch. Chicago is home to an array of brunch spots, including Lincoln Park's Batter & Berries , home of the French toast flight, or West Town's Beatnik , with its globally inspired menu and popular boozy slushies .

As you would in any big city, exercise caution when you're out and about. Keep your valuables with you at all times. Make sure to have a clear sense of your surroundings when traveling after dark, and avoid walking alone as much as possible. Neighborhoods in the South and West sides are prone to gun violence and are best avoided, especially after dark. Keep in mind that the White Sox stadium is located in the South Side, but visitors coming to games should consider using the L, which makes a stop right outside the stadium. Neighborhoods like South Loop, Kenwood and Hyde Park are not as affected as areas west of Lake Michigan (where poverty is more prevalent), but it's still best to stay alert at all times.

Getting Around Chicago

The best way to get around Chicago is via public transportation – specifically the L train. Operated by the Chicago Transit Authority, the L (short for "elevated train") is cheap and easy to use. The CTA also operates an extensive bus system with routes servicing nearly every attraction, but the bus may be difficult for newcomers to navigate. There's also the Metra regional train system that makes stops throughout downtown Chicago and in neighboring cities and suburbs. You can use public transit to reach the city from both nearby airports. O'Hare International Airport (ORD) sits 18 miles northwest of downtown and can be accessed via the L's Blue Line, and Chicago Midway International Airport (MDW) is located about 11 miles southwest of downtown and can be reached using the L's Orange Line. Cabs and ride-hailing services are also available, although high starting rates and extra charges make this option a bit expensive. Parking garage and street parking fees are pricey as well, but if you decide you need a set of wheels, rental agencies can be found at both airports.

For some of the best views of the Chicago skyline, head just north of the city to the Lincoln Park Zoo .

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Internationally recognized chefs, striking architecture, open green parks, world-renowned artwork, and a friendly Midwestern attitude come together to make Chicago one of the country’s best big cities. Here, travelers find a huge playground with an always-hot dining scene, happening shows and nightlife, and lavish hotels, plus free access to amazing concerts, public art, parks, and a spectacular lakefront.

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Photo by Amanda Hall/age fotostock

When’s the best time to go to Chicago?

Summer is the peak time to visit Chicago. During the warmer months, tourists and locals swarm the city for long days, biking and beaching along Lake Michigan, rooftop-hopping, and a variety of festivals. For milder (if not unpredictable weather), fewer crowds, and better deals, visit during the shoulder seasons of April through May and September through October, when temps hover between 50 and 70 degrees. Chicago winters are cold and windy, but this is a city that never sleeps. Dining, cocktailing, and culture continue to thrive throughout the winter, and the city gets especially festive during the holiday season.

How to get around Chicago

Most travelers to Chicago fly into O’Hare or Midway International airports. The city center is a 17-mile, $55 taxi ride from O’Hare and a 12-mile, $45 taxi ride from Midway. Alternatively, Chicago’s rapid transit system, the “L,” runs from both airports. To get downtown, take the Blue Line from O’Hare (45 minutes) or the Orange Line from Midway (25 minutes). Chicago is flat and walkable, but “L” trains, buses, and taxis will also get you anywhere you want to go.

Public transportation is also more reliable as of late with taxis in the city sometimes scarce. Use the trip planner on the Chicago Transit Authority website to figure out how to get from point A to point B. Train rides cost $2.50; bus rides cost $2.25. You’ll need a CTA Ventra fare card to ride the train, but buses also take cash. Fare cards can be purchased at vending machines at all “L” station stops and other retail locations and digitally via the Ventra Card app.

Can’t miss things to do in Chicago

- Spend time along the Chicago River. Start with a 90-minute Chicago Architecture Foundation Center River Cruise with Chicago’s First Lady; it is led by experienced docents who provide a strong foundation for your visit. You’ll discover works by visionary architects like Harry Weese and remarkable new buildings, including the 101-story, Jeanne Gang–designed St. Regis Chicago skyscraper, as well as the city’s fascinating history and culture. River cruises also offer a bird’s-eye view of the buzzy Riverwalk scene and ambient restaurants like Pizzeria Portofino . You’ll wish you had a boat of your own to zip around in and guess what, you can with Chicago Electric Boat Company , which rents everything from easy-to-drive retro electric boats, cycle boats, and pontoon boats to privately chartered yachts.

- Take your pick of incredible museums, including three of the city’s best on the lakefront’s Museum Campus: the Shedd Aquarium , Adler Planetarium , and the Field Museum, the last of which has an exceptional permanent exhibit on ancient Egypt. There are also the little-known gems, like the National Museum of Mexican Art and the American Writers Museum. Families with young children will have an especially good time at the Peggy Notebaert Nature Museum, which has a 2,700-square-foot butterfly haven and is set in the gardens of Lincoln Park, near the free Lincoln Park Zoo . The Museum of Science and Industry is also endlessly fascinating for kids of all ages. Housed in the original Palace of Fine Arts from the 1893 World’s Colombian Exhibition, the museum is a magnificent space with exhibits that include a high-tech Science Storms plus an entire U-505 submarine, the only German submarine in the United States.

- If you’re visiting in summer, get out on Lake Michigan for an entirely different view of the city, one that leaves you gob-smacked with its bright blue, ocean-like vibes. Hit North Avenue Beach for the volleyball scene and a dip in the water, rent a Divvy bike and ride along the lakefront path, or try out any number of boat tour options from Navy Pier.

- Take in Chicago’s rich and varied art scene. Colorful street murals and local galleries populate Wicker Park, while formal museums like the Museum of Contemporary Art Chicago and the extensive Art Institute of Chicago showcase impressive, well-curated collections. Next door to the Art Institute, stroll through Millennium Park for a fine introduction to friendly, proud Chicago. Take in the public art and fountains, the much-photographed Bean, the gardens, and even beyond to explore Grant Park.

- Catch a baseball game at Wrigley Field, a brick stadium built in 1914 that serves as home base for the beloved Cubs. The ivy walls surrounding the outfield, the manually updated scoreboard, the accents of fans around you—all provide a strong taste of local culture. After the game, grab a beer at one of Wrigleyville’s many iconic bars, like Guthries Tavern , or snag a seat in the chic bar across the street inside the modern Hotel Zachary .

- Chicago has its share of super towers and seeing the view from the top is stunning. The John Hancock’s 360 Chicago Observation Deck on the 94th floor has the wild “Tilt” experience with downward facing views. Go even higher at Skydeck Chicago on the 103rd floor of the Willis Tower, where you can also step out onto the glass-box Ledge .

Food and drink to try in Chicago

- Beyond deep-dish pizza and Chicago-style hot dogs, the city is home to some of the best steakhouses in the country, including Steak 48 with its fancy glass-enclosed booths and RPM Steak , as well as gastropubs and up-and-coming artisan butcher shops, like Lardon .

- Zero in on the best neighborhoods for your favorite culinary fare and you’ll understand why many people visit Chicago just to eat. Fill up on fresh Mexican food in Pilsen, try rolled ice cream and bubble tea in Chinatown, and indulge at Little Ukraine’s famous bakeries. Want a little bit of everything? Design your own foodie crawl in Fulton Market, dominated by some of the city’s best restaurants. Find Au Cheval for amazing burgers, the pretty rooftop at Aba, and Time Out Market Chicago, a food hall of stalls representing Chicago’s highest-rated local restaurants.

- Splurge-worthy tasting menu restaurants are all the rage for serious foodies, and you’ll find some of the best in the country in Chicago. Grant Achatz’s famed Alinea , one of the top molecular gastronomy restaurants in the world, and themed Next should be at the top of the list, as should buzzy newcomers that include art-forward Esmé and Filipino-inspired Kasama .

- If you’re a fan of Top Chef, you’ll find several winning chefs and their outposts here, including Joe Flamm’s Italian Croatian Rose Mary , Stephanie Izard’s Girl and the Goat and fun Duck Duck Goat, and Rick Bayless’s Xoco and Topolobampo.

- Cocktailing is an event unto itself in Chicago. When the weather is right, make your way to any number of fabulous rooftop lounges. Favorites include Cindy’s overlooking Millennium Park and the lake, Pendry Chicago’s Château Carbide for French atmosphere, Peninsula Chicago’s Shanghai Terrace (where you can also dine on some of the best Chinese food in the city), Devereaux, and the new Bar Avec decked out in greenery and coastal Spanish flair. If it’s the sultry indoors you’re seeking, don’t miss the scene and complex concoctions at the Violet Hour, artfully made cocktails at José Andrés’s Pigtail, and the playful tiki bar–themed Three Dots and a Dash .

Culture in Chicago

- Chicago hosts some excellent outdoor events and multi-stage summer music festivals, including the Lollapalooza , Riot Fest, and Pitchfork Music Festival. There’s also the Pride Parade, the world’s largest free blues festival, and Taste of Chicago , an event that draws more than 3.5 million people to sample from 70-plus food vendors. Fall brings Chicago Gourmet, hosted by Bon Appétit; the Chicago International Film Festival; and the Chicago Marathon. The year ends with Christkindlmarket, a Christmas shopping and German food market that’s part of the Magnificent Mile Lights Festival .

- It may not be New York, but Chicago’s performing arts scene holds court with iconic theater houses, like the Steppenwolf Theatre , Lyric Opera of Chicago, and Goodman Theatre. Broadway-bound plays have made their world premieres here; you may be able to catch one at the Chicago Shakespeare Theater and James M. Nederlander Theatre. You can also check out something funny at the world’s premier comedy club and a first stop for some of the best comedians of all time, Chicago’s Second City .

- Chicago has more than a few intimate concert halls that are definitely worth planning a trip around. Try to nab tickets to a show at the Chicago Theatre , Aragon Ballroom, and Thalia Hall, for starters. You might also be able to time a summer visit with a free outdoor concert at the modern Jay Pritzker Pavilion.

Local travel tips for Chicago

- Though the nickname “Windy City” initially referred to Chicago’s bloviating politicians, winters in the Midwest are no joke and the wind in Chicago is strong. If you plan to visit anytime between December and late March, bundle up and aim for a majority of indoor activities, which can include a Chicago Blackhawks hockey game, a concert at the Chicago Theatre, and dinning on Randolph Street, aka Chicago’s “Restaurant Row.”

- Getting out of the city for a day trip can be easily accomplished on the Metra rail trains or with a car rental, and there are great restaurants, museums, and parks in the neighborhoods beyond the Loop and Magnificent Mile. Check out the South Side, where you’ll find Hyde Park with its charming Sophy Hyde Park hotel and chef Erick William’s Virtue Restaurant, the DuSable Museum of African American History, and the future site of the Obama Presidential Center .

Local Resources

• Chicago magazine
• The Chicago Reader
• Eater Chicago

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USA TODAY 10Best

Readers' picks: An essential guide to the best things to do in Chicago

May 2, 2024 // By Jacky Runice

By Jacky Runice Travel Journalist May 2, 2024

I fancy myself a Chicago know-it-all (lifelong Chicagoan, radio host, journalist, nosy neighbor), but just about every Chicagoan feels the same.

This guide highlights the USA TODAY 10Best Readers’ Choice Award winners of Chicago, from awesome restaurants and bars to the greatest hotels, events, and activities in this world-class town.

Chicago has been voted among the top 10 for Best Beer City , Most Walkable City in the U.S. , and Best Summer Destination , among others — all for good reason!

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Bookmark this list for your next trip to Chi-town.

Best hotels in Chicago

Voted one of the Best New Hotels in the U.S., The St. Regis Chicago is one of the city’s many architectural marvels, designed by award-winning architect Jeanne Gang. The property includes premier butler service, nightly champagne sabrage, and The St. Regis Spa , one of Chicago’s wellness meccas.

The hotel is home to two of Chicago’s finest restaurants: Tre Dita , a love letter to Tuscan cuisine, and the airy and light-filled Miru .

Insider tip: The hotel’s rooftop terrace overlooks the city with bird’s-eye views of fireworks at Navy Pier (crowned the Best Place to See Fireworks .)

The Peninsula Chicago Hotel is an extraordinary place to roost. Z Bar, Pierrot Gourmet, and Shanghai Terrace beckon with warm weather terraces and stellar food and beverage. Afternoon tea service in The Lobby is especially festive during the holidays when the hotel does it up with live music, extravagant decor, ice skating, and spectacular overnight packages. Those are just a few reasons readers voted this establishment among the best hotels for the holidays .

Need relief from the buzz of the city? Book a seasonal treatment at Leaf Spa at Fairmont Chicago Millennium Park , voted one of the best hotel spas in the country.

Environmentally minded visitors go for the LEED Gold-certified Virgin Hotels Chicago , voted one of the country’s best eco-friendly hotels .

The Publishing House , which has earned a 10 best ranking for Best Bed and Breakfast , will completely change the minds of travelers who don’t think they like bed and breakfasts, thanks to the chic decor, laid-back ambience, and outstanding breakfast near Chicago’s Restaurant Row.

Readers voted SOPHY Hyde Park as a Best Boutique Hotel . The South Side vibe combined with the hotel's smart rooms, artistic indoor, and outdoor spaces complements the cultural essence of the neighborhood that the Obamas once called home.

Best Chicago restaurants, cafes, and sweet shops

When that midafternoon snooze hits, sip a phenomenal cup of joe at Big Shoulders Coffee , a Best Independent Coffee Shop winner. With a former chef-turned-coffee roaster at the helm, stop here for no-nonsense artisan beans, roasted to perfection.

There are handmade candies galore at Windy City Sweets , a 2023 winner for Best Candy Store , from nostalgic treats to signature, homemade fudge, s’mores, and more. At Katherine Anne Confections , which got a nod for Best Chocolate Shop , you’ll find seasonal flavors plus classics like salted caramel.

Stock up on bakery goods or enjoy biscuits and gravy and two-fisted sandwiches at Wheat's End Cafe , one of the best gluten-free bakeries in the country.

In a city that takes its pizza seriously, both Chicago’s Pizza and Robert’s Pizza and Dough Co. made the top 10 for best gluten-free pizzerias for their in-house crusts and array of toppings.

The Oakville Grill & Cellar , one of 2024’s best new restaurants, has a great happy hour and weekend brunch. Featuring ingredients from farms and ranches across the Midwest, enjoy menus for lunch and dinner on the all-season patio.

Chicago has a plethora of notable steakhouses, and Asador Bastian , a Basque-inspired chophouse in River North's Gallery District, is something really special. Another Best New Restaurant winner, here you'll enjoy several varieties of flame-kissed beef, seafood, and a tortilla Española that will whisk you right to San Sebastian, Spain.

Traveling to or from Chicago? Don’t overlook the restaurants at O’Hare Internationl Airport , one of the best airports for dining . Notable stops include Rick Bayless’ Tortas Frontera, Berghoff Cafe for German items, cheeseburgers at Billy Goat’s, or Gold Coast Dogs for Chicago-style hot dogs and Italian beef sandwiches. For drinks, hangout at Goose Island Beer Company or Publican Tavern.

Best Chicago bars

With more than 160 Chicago breweries capturing the imagination and outsider appeal of craft beer culture, this Best Beer City continues to bag a barrel-full of awards.

Pilot Project Brewing , a springboard for startup breweries bringing exciting new brews from around the world, and Sleeping Village are both award-winning beer bars . Visit the Pilot Project Brewing’s incubator and taproom to sample beer, craft non-alcoholic brews, tea, and coffee.

Among 2024’s best new breweries , Black-owned Funkytown Brewery brings diversity to the craft brew space, winning multiple awards for suds like Hip-Hops, R&Brew, and Cuffin’ Season. Also voted a Best New Brewery by USA TODAY 10Best readers: Turner Haus, a Black, family-owned enterprise in Bronzeville. They brew and name beers after the family matriarchs.

Readers voted Chicago’s first botanical brewery and restaurant, Forbidden Root , as a Best Brewpub for its continuously rotating menu of Midwestern food and beverage tweaked with the seasons. Another Best Brewpub: Old Irving Brewing Company .

Don’t miss women-owned ERIS Brewery and Cider House , which topped the list as Best Cidery in the country.

Best events in Chicago

Chicago teems with festivals. Windy City Smokeout, an outdoor country music and BBQ festival, was a winner of the Academy of Country Music Awards' Festival of the Year, as well as a USA TODAY 10Best Readers’ Choice Award for Best Specialty Food Festival . Count on an impressive lineup featuring some of country music’s biggest names, along with the ultimate BBQ and craft beer from around the country.

A Chicago tradition since 1980, the Taste of Chicago thrills locals and visitors who want to experience Chicago’s expansive food scene, peppered with live music, entertainment, and family fun. The free-admission event takes place over three days in Grant Park. Chicagoans don’t mourn the end of festival season when the first leaves float off trees; they just keep partying!

The Chicago German-American Oktoberfest is a wunderbar Best Oktoberfest filled with music, dancing, and lots of wurst, pretzels, and beer.

The Magnificent Mile Lights Festival winds down Michigan Avenue and up to a top 10 spot on the Best Holiday Parade list. Stroll over to Christkindlmarket , the award-winning German-style bazaar that will fill you with holiday cheer.

Best attractions and other things to do in Chicago

Whether participant or fan, the Windy City has a roster of activities for sports fans year-round. One of two classic historic ballparks still standing in the U.S., Wrigley Field , clutched a spot as one of the best MLB stadiums . The 1914 ballpark has modern amenities, from a sensory room to electric vehicle charging stations. Don’t miss iconic Chicago snacks like Garrett Popcorn, Home Run Inn pizza, Vienna Italian beef, and Anthony Bourdain’s favorite, Hot Doug’s.

When the dogs start barking, get off of your feet and onto Chicago’s First Lady Cruises , a Best Boat Tour winner, an ideal way to see iconic architecture, or settle into a kayak to paddle the Chicago River.

This city has numerous must-visit institutions, like the internationally admired Art Institute of Chicago . This Best Art Museum is rife with Hoppers, Picassos, Van Goghs, and O’Keefes.

The most popular exhibit every year at the National Museum of Mexican Art is for the Day of the Dead. The museum dazzles with gleaming altars, whimsical sugar skull sculptures, and eye-popping art celebrating the dearly departed in colorful ways that are anything but grim. It ranks as one of the best free museums in the country.

Brush up on your science smarts and feel the physics at the massive Museum of Science & Industry , the largest science museum in the Western Hemisphere and a winner for Best Science Museum in the country.

Since Chicago was deemed one of the most walkable cities in the U.S. , you can easily torch some calories at the city’s first elevated park, The 606 ; the 18.5-mile Lakefront Trail ; walking paths at Millennium Park ; or just tooling around the neighborhoods.

About Jacky Runice

Born in Bucktown when bulletproof was a home safety choice and not a coffee order, Jacky Runice has been knocking around Chicago as a professional print, online and broadcast journalist and editor specializing in separating the riff from the raff in culture, entertainment, food, travel and pure unadulterated fun. Jacky is a member of the International Food, Wine & Travel Writers Association (IFWTWA). In her best Chicagoese, Jacky asks, "Who has the time or money to blow on hotels, attractions, restaurants, exhibits and activities that blow?"

Read more about Jacky Runice here.

Connect with Jacky via: Website | Facebook | Instagram | Twitter | Pinterest

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24 travel tips every first-time Chicago visitor needs to know

Chicago is a friendly city for tourists, but we’ve collected a few useful things to know before you arrive.

Welcome to Chicago! We’re glad you’re here (or considering a trip, at least). Whether you’re visiting on business or pleasure, we know it can be daunting to travel to a new city for the first time. There are logistical hurdles: figuring out the public transportation options , navigating the grid system, knowing the best neighborhoods to stay in. And then there are the cultural questions: What’s the best time to visit? What should you do with your time? Is deep dish truly all it's cracked up to be? We’ve drawn from our experience as Chicagoans, and polled our own visiting friends, to help prepare you for what you should know as a new arrival.

RECOMMENDED: Your essential Chicago travel guide

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Chicago travel tips for first-time visitors

1.  Take the "L" to and from the airports.

Beat the traffic and surcharges and skip the taxi or rideshare when you arrive. Our regular Chicago Transit Authority "L" (short for "elevated") trains offer direct service to both Chicago airports: the Blue Line serving O’Hare and Orange Line for Midway International Airport. A $2.50 fare from Midway or $5 from O’Hare for regular service downtown in under an hour feels like a steal to us when we travel to other cities without such easy airport access.

2.  Get a three-day (or seven-day) CTA pass.

No need to rent a car if you're sticking close to the city. In the smartphone age, the CTA is easy enough to navigate even for newbies. Fares, though, can be a little harder to keep track of: You could load a dollar amount onto a Ventra card and then try to do the math every time you spend $2.50 on a train ride and $2.25 on a bus—or maybe that counted as a $0.25 transfer if it was within two hours of your last ride? Much easier to buy a three-day pass, which is $15 for 72 hours of unlimited rides. If you’re staying longer, a seven-day pass on a new Ventra card will run you just $20—totally worth it if you’re spending that much time here. All can be purchased from the Ventra vending kiosks at either airport and any CTA station, as well as many supermarkets and pharmacies.

3.  If you do drive, download the ParkChicago app.

If you’re driving into the city and want to use your car while you’re here, download ParkChicago ( parkchicago.com ) to your phone for all your street parking needs. Create an account with your license plate number and link a credit card, and you’ll pay in the app using the zone number printed on signs like this one where paid street parking is available. Rates vary by neighborhood. (Many residential streets will be marked permit-only, while a blessed few unmarked streets are actually free to park on—check carefully for signage before you assume.)

4.  While you’re at it, download all of these apps to help you get around.

Google Maps, Apple Maps or Waze will give you solid directions, and the Uber and Lyft apps can find you a ride at just about any address and any time of the day or night (most rideshare drivers work for both services, in our experience). Transit Stop  is our favorite for real-time arrival projections for L trains and bus routes, and if you’re a nervous navigator, you can tell the app exactly where you’re going and it will give you a heads up when your stop is approaching. Check out more transportation apps we love here .

5.  Get the gist of the grid system.

Unlike a lot of cities, Chicago’s streets are laid out on a generally reliable grid system. Here’s the quick-and-dirty version: The intersection of State and Madison Streets, smack in the middle of the Loop, is the zero point of the grid. Street numbers fan out from there on north-south and east-west axes, and every eight blocks (outside of the Loop, at least) equals a mile. There are angle streets and river branches and historical quirks here and there to create confusion and six-corner intersections, but the grid is a solid foundation for getting around. Also, if you remember nothing else, east is always towards the Lake. 

6.  Give yourself plenty of time to get where you’re going.

In a city of almost 3 million people, delays are almost bound to happen whether you’re on the L or on the expressway (which, by the way, is what we call our controlled-access highways, a.k.a. freeways, interstates or motorways). If you’re trying to make an appointment with a rigid start time—whether it’s a meeting, a dinner reservation or a theater curtain—allow more time than you think you need, just to be safe.

7.  Tipping is standard for many services. Here's how to do it.

In the United States, tipping is customary for service in several situations, and the standard rates in Chicago may be higher than you’re used to elsewhere in the country. At sit-down restaurants, where you have a server taking your order at your table and seeing to your needs through your meal, you should tip at least 20 percent of your total bill for good service. If you’re out for drinks, a dollar per drink is usually fine if you’re ordering from the bar—more if they’re complicated cocktails.

If the establishment accepts credit cards, you can add the tip onto your total when you sign the bill. Many restaurants and coffee shops also now have a payment system that allows you to add a tip automatically to your bill via credit or debit card, and calculates the percentage for you.

In the wake of the COVID-19 pandemic, some restaurants and bars will add a surcharge to your bill to compensate for lost revenue and increased costs as a result of the pandemic. This charge is not a replacement for a tip, and you should still prepare to add a tip on your bill. 

Other situations will call for cash tips: Give a valet parking attendant a couple of dollars when they retrieve your car, and tip a bellhop or skycap a buck or two for each of your bags they handle. Hotel housekeeping staff should be tipped about $5 per day of your stay, which you can leave out in the room when you check out.

8.  You might need cash in other situations, too.

While it’s increasingly uncommon, there are a remaining few cash-only venues around the city that don’t accept credit cards—among them, some of our favorite dive bars and cheap eats establishments. It’s also good to have cash on hand if you’re planning on visiting any summer street festivals or looking to make a purchase at art or craft fairs; many small vendors can now accept credit cards via services like Square, but it's a good idea to bring cash just in case (and to avoid the high fees that are often found at on-site event ATMs). 

9.  Be prepared to have your purse or bag searched at large venues.

Whether you’re a business commuter or a tourist, unless you’re driving your own car everywhere you go you’ll probably be carrying a purse, tote, briefcase or bag of some kind to lug your stuff around. Security precautions at certain large venues—stadiums and ballparks, theaters, concert venues and music festivals—will mean an agent asking to take a cursory peek inside your bag before you go in; it’s standard practice. Certain venues, though, won’t allow very large bags or specific items inside at all, and they won’t be able to hold anything for you at the gate or the cloakroom. If you don’t want to find yourself making a trip back to your car or hotel and missing part of your event, it’s best to check the rules ahead of time.

10.  Skip the chains and stay in one of these local hotels…

You can stay in a Hyatt or a Hilton anywhere you go. When you’re here, splurge instead on one of the best hotels in Chicago —unique digs like the Chicago Athletic Association or the Ace Hotel. Or look at the city’s best boutique hotels , gems like the Freehand, Hotel Lincoln or the Robey.

11.  …or try an Airbnb, like one of these intriguing options.

Rent out an extravagant apartment or a homey condo for the duration of your stay—we’ve chosen some of the city’s most attractive options  here .

12.  There’s nothing “too touristy” about taking a tour.

The Chicago Architecture Foundation’s boat tours along the Chicago River are, frankly, one of our favorite reasons to have out-of-town guests (and they're fun to check out even when we don't have out-of-town guests). It’s just one of dozens of the best tours of Chicago , including walking tours and bike tours. You can also find food tours or brewery tours to maximize your use of time.

13.  Or take a self-guided tour of our best public art.

The unnamed Picasso sculpture in Daley Plaza and, more recently, Millennium Park’s Cloud Gate (a.k.a. “The Bean”) have become symbols of the city. But there’s great public art to be found all over the place in Chicago, from murals by Hebru Brantley to mosaics by Marc Chagall to sculptures like Lorado Taft’s Fountain of Time . Even the enormous facade of the Merchandise Mart  has become a canvas for video art with the Art on theMART program.

14.  Bring comfortable walking shoes.

Chicago’s terrain is relatively flat and you won't find many hills to climb, unless you’ve built a side trip to one of our nearby hiking trails into your visit. But you’ll probably wind up doing more walking than you might think. Our city blocks are long, and both CTA stations and parking spots can be a good distance from your destinations.

15.  Wear layers. Year-round.

The weather in Chicago can fluctuate wildly in a matter of hours: Summer storms roll in out of nowhere, or the temperature rises 30 degrees Fahrenheit from morning to midday. If you’re going to be out on the town all day, it’s best to dress with options to shed or layer on as the day progresses. Even at the height of summer or winter this is true: Pitchfork  or Lollapalooza summer festival attendees in tank tops and short-shorts often find themselves wishing for a hoodie when the evening chill sets in, and there’s nothing worse than the overheated feel of being too bundled up on a packed CTA car in January.

16.  But summer is what we do best.

We can make a great case for every season in Chicago, but it’s hard to deny that summer is when visitors and residents alike can take the best advantage of what the city has to offer. After a long winter, Chicagoans scramble outside to outdoor dining and rooftop bars , our great public parks , Cubs and White Sox games, and of course to one of Chicago’s finest features—the 26 miles of beaches and open lakefront that make up the city’s eastern edge. We take our summers seriously.

17.  Speaking of summer, street festivals are a must.

We’ve already breathlessly sung the praises of summer in Chicago, but summer festival season deserves a shoutout all its own. Every weekend from spring well into autumn, there are multiple lively festivals to choose from, each with delicious food, live music and other fun activities to explore. From art fairs and cultural and LGBTQ+ festivals to exuberant, jam-packed concerts and celebrations of a specific food or drink item (e.g. Ribfest, Apple Fest and something called Seltzerland), there’s truly something for every taste. 

18.  Get out of downtown.

A lot of the city’s hotels are clustered in River North, on the Mag Mile and in the Loop. Not coincidentally, so are a lot of chain restaurants and tourist traps. (It’s no surprise the only TGI Friday’s in the city is just off Michigan Avenue). Just like visiting Times Square doesn’t mean you’ve seen New York City, if you want to see how Chicago really lives, you’ll need to venture out into the neighborhoods. We like to call this a city of neighborhoods, and each area of the city has its own identity and attractions. Start here with our neighborhood guides .

19.  You could spend a week on museums alone.

Remember we said you’d be doing a lot of walking? A good chunk of that could take place inside Chicago’s must-see museums . The Art Institute alone is the second-largest museum in the United States—at over a million square feet and with 300,000 pieces in its collection, don’t expect to knock it off your list in an afternoon. You’ll have to pay admission to most of the big institutions; free days are generally offered only to Illinois residents, but a Chicago CityPASS is a good way to get discounted admission to several. And plenty of smaller free museums and galleries never charge admission and are definitely worth your while.

20.  We still love Old Style, but we’re increasingly a craft beer town.

While Chicago has always been a beer-loving city, there was a dark period of a decade or so after Peter Hand Brewing closed in 1978 when no beer was actually being made here. The closest you could get to a “local brew” was stuff from Milwaukee. But in the late ’80s and early ’90s, a few hops-headed entrepreneurs launched Chicago’s first brewpubs, where beer was made and drank on the same premises. One of these, Goose Island, made its first foray into bottling and distribution in 1995; within another decade, the craft beer boom had begun. Now, Goose sits alongside names like Half Acre, Revolution and Lagunitas on any list of Chicago’s best breweries , but there are well over 100 breweries operating in the city and suburbs, many of which have attached taprooms and offer brewery tours,  and events like FOBAB (Festival of Barrel-Aged Beers) and Illinois Craft Beer Week have become tourist draws all their own.

21.  You can (and should) skip the Magnificent Mile.

We mentioned the chain restaurants around Michigan Avenue. Well, these days most of the shops lining the pedestrian-packed sidewalks of the Mag Mile are also outposts of department stores and brands you can find elsewhere in the country (or even elsewhere in the city). For more unique retail, look where the locals do: great shopping neighborhoods like Wicker Park and Bucktown, Lincoln Park, Lakeview, Logan Square or Andersonville.

22.  Experience the local sports culture.

From the Michael Jordan-led Bulls dynasty in the ‘90s to recent championship titles by the Blackhawks, Cubs and Sky, Chicago prides itself on heavy-hitting sports teams and wildly passionate fans. With most stadiums easily accessible by train or bus and single-game tickets relatively affordable if you book in advance (it’s possible to get White Sox tickets for as little as $8 , for example), cheering on one of the many local teams with a hot dog and an Old Style in hand is a great way to spend an afternoon in Chicago. 

If you’re not much of a sports person, it still helps to know when the local teams are playing for getting-around purposes. If you’re heading north on the Red Line and the Cubs are in town, be prepared for a packed-to-the-gills train or bus and possible delays. There’s even a handy website for quick references.

23.  There’s way more to Chicago theater than downtown, and more to comedy than Second City.

The big musicals that visit the Loop under the banner of Broadway in Chicago are a major tourist draw; some visitors build their trips to Chicago around getting to see Broadway-style shows without having to go to New York. And hey, we’re not going to tell you not to see Hamilton  (or whatever other marquee show is playing) if that’s what brings you here. But Chicago’s homegrown theater isn’t centralized around a theater district. Instead, theaters large and small have cropped up across the city and suburbs; you can catch a show in neighborhoods from Lincoln Park to Jefferson Park, Back of the Yards to Grand Crossing, and many residents become loyal subscribers of the theaters in their own backyards. Similarly, while Second City has produced a lot of famous names, it’s not the only game in town for the improv and sketch comedy Chicago’s famous for. You’ll find a greater variety of shows (and possibly more comfortable seats) at Lincoln Lodge or the Annoyance, and many more of the city’s best comedy nights take place in bars, bookstores and other non-theater venues.

While you’re here

Best things to do in Chicago that locals and tourists will love

• Things to do

These attractions and events are fun for first-time visitors and residents alike

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Chicago Travel Guide

Last Updated: April 15, 2024

Best known as the “Windy City” because the local politicians blow hot air, Chicago is one of my favorite cities in the entire United States — especially in the summer when the weather is perfect.

Because the winter is harsh here, the city comes alive in the spring and summer as residents buzz about after being confined inside. There’s not one person I know who doesn’t say, “You can’t get better than Chicago in the summer.”

Chicago’s biggest draws include its green space, the most famous being Grant and Millennium Park, home to the iconic Chicago Bean sculpture (officially known as Cloud Gate). The city also boasts world-class food, fun nightlife, lots of activities, outgoing people, and an uplifting atmosphere. There’s a lot to do here for people of any budget or travel style.

This travel guide to Chicago can help you plan a fun and affordable trip without breaking the bank!

Table of Contents

• Things to See and Do
• Typical Costs
• Suggested Budget
• Money-Saving Tips
• Where to Stay
• How to Get Around
• How to Stay Safe
• Best Places to Book Your Trip
• Related Blogs on Chicago

Top 5 Things to See and Do in Chicago

1. Relax in Grant and Millennium Park

Located downtown, these gigantic parks provide a great place to hang out, have a picnic, or go for a run. People play chess here when the weather is nice and during the summer there are a lot of free concerts. Grant Park stretches along Chicago’s waterfront and is the larger park, while Millennium Park is the subsection where the famous “Chicago Bean” sculpture is located. Officially titled “Cloud Gate,” this iconic work of public art is a must-see while visiting Chicago. Starting at noon on the 1st and 3rd Saturdays April-November, the Chicago Cultural Center hosts walking tours focusing on the art of Millennium Park.

2. Stroll down the Magnificent Mile

Often nicknamed “Mag Mile,” this stretch along Michigan Avenue from the Chicago River to Oak Street is known for its upscale designer boutiques. In fact, rent here is the 3rd highest in the US (after Fifth Avenue in New York City and Rodeo Drive in Beverley Hills). Even if you don’t want to blow your budget on some expensive threads, it’s still an experience to stroll down the avenue and take in the sights, and the people, and enjoy the view of the Chicago River. There are several landmarks and attractions along the avenue too, including the 360 Chicago observation deck for expansive views over the city.

3. Experience St. Patrick’s Day

Next to Ireland , Chicago is the best place to be on March 17th. To honor its large Irish-American population, the city dyes its river green, hosts a huge parade, and parties until the sun comes up (complete with copious amounts of green beer). The tradition began in 1843 when the city’s first Irish parade was held, but it wasn’t until 1962 that the dyeing of the Chicago River started, at the suggestion of a local plumber’s union. This union is still responsible for the green river each year, though they won’t divulge their secrets on the dye used (it’s environmentally friendly, though). Take a river cruise on the emerald waters or snap a pic from the sidelines and enjoy. This is one of the biggest days of the year here!

4. Have fun at Navy Pier

This 3,300-foot-long (1,010 meters) pier on the shoreline of Lake Michigan started off as a shipping pier but has also been a prison for draft dodgers during World War II, a Naval training center, and a temporary university campus. Since 1995, it has reopened to the public in its current form, and become sort of like a carnival in a city. It’s Chicago’s second-most visited tourist attraction (after The Bean) and contains some rides, a Ferris wheel, lots of restaurants, a Shakespeare theater, boat tours, a large number of beer gardens, mini-golf, and more! It’s a good place to have some silly fun (especially if you have kids).

5. Try deep dish pizza

Chicago developed the deep-dish pizza, as well as the stuffed crust pizza, and no trip is complete without trying both. The deep-dish pizza was invented in 1943 by Pizzeria Uno, which is now a national restaurant chain. For something more local, Chicagoans swear by Lou Malnati’s. Personally, I’m not usually a huge fan of deep dish but I was impressed by theirs! If you really want to indulge, hop on a pizza tour offered by Chicago Pizza Tours, where you’ll get to sample all the varieties of pizza on offer in this city. Tours start at $59 USD.

Other Things to See and Do in Chicago

1. visit the oriental institute museum.

The Oriental Institute (OI) of the University of Chicago is a leading research center for the ancient Middle East. Their museum is home to a huge archaeological collection of objects from the Near East, including ancient Egypt, Israel, Syria, Turkey, Iraq, and Iran. Established in 1919, the museum has all kinds of artifacts, photographs, historical records, and even a giant 17-foot-tall statue of King Tut that weighs over six tons! Suggested admission is $10 USD.

2. See the Chicago Cultural Center

The former site of the Chicago Public Library, this historic landmark is known for its exquisite Tiffany mosaics, especially in its performance venue Preston Bradley Hall. Its rooms were inspired by the Acropolis of Athens , the Palazzo Ducale in Venice , and the Palazzo in Florence . It has changing art exhibits, events, performances, and free guided tours of the historic building (Thursdays and Fridays at 1:15pm). Check the website to see what events and performances are available during your visit. It’s free to visit.

3. Get Shown Around By a Local

Chicago has a local greeter program, which offers free walking tours of various neighborhoods from a knowledgeable local. This is a great opportunity to see more of the city while learning about it directly from an expert local guide who can answer all your questions. You can sign up at chicagogreeter.com (you need to do it at least 10 days in advance). I highly, highly, highly recommend doing this!

4. Stop by the City History Museum

This museum provides a solid overview of the history of Chicago, with an in-depth focus on the Great Chicago Fire in 1871 that burned down most of the city (the fire killed 300 people and left 100,000 people homeless. Abraham Lincoln’s final draft of the Emancipation Proclamation was lost in the fire too). The museum has 22 million items, including President Lincoln’s deathbed and the clothing he and his wife wore when he was assassinated. The rotating exhibitions highlight different events and cultural groups that contributed to the city’s history, like the Polish immigrants that came to the city starting in the mid-1800s and the way art was used to influence societal change during the 1960s and 1970s. Admission is $19 USD.

5. See the Cubs play

Locals are incredibly passionate about their baseball team. Get in the spirit and head out to a game at the Cubs’ home stadium, Wrigley Field. Even if you don’t know a lot about baseball, it’s still super fun. It gets really intense when the Cubs play Chicago’s other team, the White Sox. The season goes from March-November and tickets usually start around $15 USD for the upper deck and go up from there.

6. See Robie House

This Frank Lloyd Wright masterpiece, completed in 1909, is a premier example of his Prairie School design. From the overhanging roofline to the expansive interior, the home design balances simplicity with perfectly placed details. The choices of each element, like the limestone incorporated into the exterior and the iridescent glass of the windows, was done with intention to bring a feeling of expansive natural landscapes. Wright helped make Chicago architecture famous and this house is one of his best-known buildings. Today, the house is located on the University of Chicago campus and is listed as a UNESCO World Heritage site along with 8 other of Wright’s most emblematic works. Admission starts at $20 USD, which includes a guided tour of the interior.

7. Visit the Art Institute of Chicago

This is Chicago’s most famous museum, and in fact one of the oldest and largest art museums in the world. From photography to architecture to textiles, it houses a collection that includes works by Eva Hesse, David Hockney, and Ellsworth Kelly. This is where you can see the Hartwell Memorial Window designed for Tiffany Studios more than a century ago and a famous Vincent Van Gogh painting, The Bedroom. You’ll also find a 12th-century statue of the Buddha and 16th century German armor made for jousting. Founded in 1879, the museum has over 300,000 items in its permanent collection and hosts upwards of 30 special exhibits each year. Admission is $32 USD.

8. Take a food tour

Get to know the city through its culinary scene, from deep-dish pizza to microbreweries to Chinatown’s best restaurants. Get Your Guide offers a huge assortment of tours depending on your culinary interests. Usually, they involve some educational element. You can combine your love of food with architecture, history, or kayaking. Others focus on certain items, like donuts, or specific neighborhoods, like the culturally diverse Westside. There’s even a tour that combines traditional Chicago staples dishes with gangsters like Al Capone. Tours start from $55 USD and go up from there.

9. View some war-inspired art

The National Veterans Art Museum (formerly The National Vietnam Veterans Art Museum) is a great yet seldom-visited museum. It features over 2,500 works of art created by Vietnam war veterans and, more recently, veterans from Iraq and Afghanistan. The entrance has 58,226 dog tags hanging from the ceiling, representing the soldiers who died in Vietnam. It’s a stark, somber reminder of our overly-romanticized notion of war. Admission is free, though donations are welcomed.

10. Get acquainted with nature

Established in 1857, The Peggy Notebaert Nature Museum is a beautiful institution with roof-top gardens and plenty of information about the ecosystems surrounding Chicago. The “butterfly haven” is the most interesting — it’s an enclosed space with over 200 species of butterflies, a waterfall, and garden paths. There’s an exhibit about the natural wetlands of Illinois and the endangered species that live there and a resource center focused on sustainability. Outside the building you’ll find the Deb Lahey Nature Trails where you can walk through and learn about plant life native to the area. They also organize dozens of educational programs for both kids and adults. This museum is open daily and it costs $17 USD.

11. Catch an improv show

Chicago is the birthplace of improv comedy and a visit to the city wouldn’t be complete without catching a show. There are tons of companies here — many of which have given birth to comedy greats like Tina Fey, Amy Poehler, Stephen Colbert, Mike Myers, Steve Carell, Eugene Levy, Bill Murray, and a ton of others. Second City is the most popular venue/troupe. Tickets start at around $25 USD. The iO Theater has been a hotspot for comedy and improv in Chicago for decades, has four stages, and continues to put on shows five nights a week. Tickets here star around $23. The Laugh Factory, ComedySportz, and Zanies are just a few of the other popular venues in the city.

12. Go to the beach

When most people think of Lake Michigan, they don’t imagine sand, waves, and water as far as the eye can see — but it’s there! Downtown Chicago runs right next to the shore and offers a little piece of nature in a city of skyscrapers. North Avenue Beach is one of the most popular because of its location just north of downtown. You can even rent SUPs, kayaks, and jet skis there. Loyola Beach is a little further north and is much quieter, if you want to get away from the crowds. 31st Street Beach is at the edge of Burnham Park, south of downtown, and another place to find rentals for water activities. 57th Street Beach, Montrose Beach, and Ohio Street Beach are other most popular choices.

13. See the Willis Tower

The Willis Tower (formally the Sears Tower) held the title of the world’s tallest building for 25 years. Currently, it’s the third-tallest building in the US and the 23rd tallest in the world. Standing at 1,450 feet (110 stories) tall, visitors can take the elevator to the SkyDeck (the highest observation deck in the United States) for panoramic views over Chicago. For those who don’t mind heights, the SkyDeck’s Ledge is a glass box extending over 4 feet over the city, offering heart-pounding views of the urban landscape below. Admission is $32 USD.

14. Explore the Field Museum of Natural History

This museum was built for the World’s Columbian Exposition of 1893 to house its impressive biological and anthropological collections. Built in the Neoclassical style, the museum has 24 million objects, including exhibits on everything from mummies to meteorites, and more. Some sections focus on specific peoples, like the Maori of New Zealand. Others highlight flora and fauna, such as birds native to North America, and plant life from around the world. 3D movies are a fun way to learn more about interesting topics, like dinosaurs that once lived in Antarctica. There’s also a library with over 275,000 books. Admission starts at $30 USD. The expansive garden of native plants outside the museum is free to visit.

15. Stroll the Chicago Riverwalk

Do like the locals do and hang out on the south bank of the Chicago River, where you can walk the Chicago Riverwalk from Lake Shore Drive to Lake Street (it’s a little over a mile). Grab a glass of wine at the Riverwalk Wine Garden by City Winery and enjoy some people-watching. It’s a gorgeous place for a stroll in the summer! At night, you can see the projections of Art on theMART, the largest permanent digital art exhibition in the world.

16. Visit the Adler Planetarium

This was the first planetarium in the United States. It boasts immersive theater programs, rotating exhibitions, and other fun events (including lectures). You can virtually experience the depths of powerful black holes and the heights of Voyager 1, the farthest manmade object from Earth. There are also awesome special events, like Adler After Dark which lets you explore the planetarium while enjoying drinks and live entertainment. Admission starts at $19 USD.

17. Take a bike tour

To explore the city’s main sights and cover a lot of ground, take a bike tour. Bobby’s Bike Hike uses expert local guides so you learn a ton about the city. They offer food tours, neighborhood tours, and tours of Chicago’s main attractions, all by bike. The Lakefront Neighborhoods tour is a good way to get familiar with the city and its layout. The Bikes, Brews, & Bites tour combines gives you a chance to sample a few iconic Chicago dishes and learn the history behind them while exploring and enjoying local craft beers along the way. It’s a fun way to explore and you get to see a lot too! Tours start at $46 USD.

18. Float on the Chicago River

Getting out on the river is a great way to see the city from a different perspective. Paddle around in a kayak from Urban Kayaks, bike your way through the water on a Cycleboat (it’s also BYOB!), take an architecture boat tour, or go traditional and take a dinner cruise. Prices vary greatly depending on what you choose, but expect to pay at least $45 USD to get out on the water.

Chicago Travel Costs

Hostel prices – During peak season, a bed in a 4-6-bed dorm costs about $50-70 USD and $35-65USD in the off-season. For a room with eight beds or more, expect to pay around $45-60 USD in peak season and $30 – 45 USD off-peak.

A basic private room starts at $136 USD during peak season and goes up from there. Prices drop to around about $70-120 USD in the off-season. Free Wi-Fi is standard and most hostels have self-catering facilities. Some hostels also offer free breakfast and a few have a bar/restaurant on premises.

Budget hotel prices – Budget two-star hotels start at $110 USD per night in peak season. In the off-season, prices drop to around $85 USD. Expect basic amenities like free Wi-Fi, AC, TV, and a coffee/tea maker.

There are also lots of Airbnb options in Chicago. A private room starts at $40 USD per night while an entire home/apartment averages $130 USD per night. Expect to pay double (or more) if you don’t book in advance.

Food – Chicago has lots of fast food and street food options. The city is famous for deep dish pizza, Italian beef sandwiches, and Chicago dogs, which are simple hot dogs dressed with mustard, hot peppers, tomato slices, green relish, and a pickle spear. Another dish to try in the city is a jibarito sandwich, which was created by Puerto Rican immigrants. It’s typically thin-sliced steak, tomato, lettuce, cheese, and mayonnaise between a “bun” of smashed and fried plantains.

You can get a huge hot dog, a chili dog, or a few tacos for under $5 USD, or a sandwich for under $10 USD. A personal deep dish pizza starts at about $13 USD (Lou Malnati’s Pizzeria is the best place to order it). Fast food (think McDonald’s) is around $11 USD for a combo meal.

You can eat at an inexpensive casual restaurant with table service for around $25 USD. For a three-course meal with a drink, expect to pay closer to $55 USD.

Chinese food is around $9-13 USD and you can find Thai food for around $13-15 USD. Beer is $7 USD, a cocktail is $11-15 USD, and a glass of wine is $10 -12 USD. In terms of non-alcoholic drinks, a latte/cappuccino is $5 USD while bottled water is $2.50 USD.

If you cook your own food, expect to pay around $50-60 USD per week for basic staples like pasta, rice, vegetables, and some meat. There are plenty of grocery stores around, even close to the downtown area. Mariano’s is known for high quality and low prices.

Backpacking Chicago Suggested Budgets

If you’re backpacking Chicago, expect to spend about $80 USD per day. This budget covers a hostel dorm, using public transportation, cooking your own food, and free attractions like walking tours, the parks, and the beaches. If you plan on drinking, add $20 USD to your daily budget.

A mid-range budget of about $240 USD includes staying in a private accommodation, eating out for most meals, enjoying a couple of drinks, taking the occasional taxi, and doing some paid activities like museum visits or a bike tour.

On a “luxury” budget of about $430 USD or more per day, you can stay in a hotel, eat out anywhere you want, drink as much as you’d like, take more taxis or rent a car, and do more paid activities. After that, the sky is the limit!

Chicago Travel Guide: Money-Saving Tips

Chicago is an expensive city, especially when it comes to attractions and accommodation. But, like any major city, there are always pockets of affordability if you know where to look. Here are some ways to save money in Chicago:

• Get the Chicago City Pass – There are two different sightseeing passes available for Chicago. The CityPASS lets you choose either three or five attractions from a list of nine. Prices range from $102 USD to $139 USD. Go City passes offer more flexibility with entrance to more than twenty-five attractions. The All-Inclusive pass gives you entrance to an unlimited number of attractions. Prices for this pass range from $124 USD for a one-day pass to $234 for a five-day pass. The Explorer Pass gives you entrance into a specific number of attractions from the list. Prices range from $84 USD for a two-attraction pass to $189 for a seven-attraction pass. The Explorer passes are valid for sixty days. These passes are worth it if you are going to see a lot of attractions. Do the math before you get them though!
• Redeem hotel points – Be sure to sign up for hotel credit cards and use those points when you travel. There’s nothing better than free accommodation and most cards come with at least 1-2 nights free. This post can help you get started with the basics so you can start earning points today and have plenty for your trip.
• Stay with a local – Couchsurfing is the best way to save money on accommodation in Chicago. You’ll not only get a free place to stay but you get to connect with a local who can share their insider tips. It’s perfect for budget travelers who want to make connections.
• Look for the happy hours – The Ultimate Happy Hours website lists all the happy hour drink and food specials around Chicago. It’s updated with new info frequently!
• Go on a free walking tour – This is a great way to learn the history behind the places you are seeing and avoid missing any must-see stops. Free Chicago Walking Tours has several interesting walking tours that can show you the main sights. Just be sure to tip your guide at the end!
• Bring a water bottle – The tap water here is safe to drink so bring a reusable water bottle to save money and reduce your plastic use. LifeStraw is my go-to brand as their bottles have built in filters to ensure your water is always clean and safe.

Where to Stay in Chicago

Accommodations are expensive in Chicago. However, there are a lot of hostels (with private rooms too) and budget hotels that can help keep your costs down. Here are my recommended places to stay in Chicago:

• Found Chicago River North
• Chicago Getaway Hostel
• Parthenon Hostel
• Freehand Chicago

For more hostel suggestions, be sure to check out my complete list of the best hostels in Chicago!

How to Get Around Chicago

Public Transportation – The Chicago Transit Authority operates the L Train (elevated subway train) and the bus system. Their website has a complete list of routes and planning tools. The L Train costs $2.50 USD per journey, which is automatically deducted from your Ventra card (a rechargeable card that you can buy at any L station). The Ventra card itself costs $5 USD, but that amount gets refunded when you register the card.

The train from the airport costs $5 USD. You can also take a city bus, which is $2.25 USD.

There are also passes available, including a one-day pass for $5 USD, a 3-day pass for $15 USD, and a 7-day pass for $20 USD.

Water Taxis – Water taxis are a fun way to get around some parts of Chicago. A one-way ticket between two docks costs between $6USD. You can get an all-day pass with unlimited trips for $10. If you’ll be staying in the city longer, a 10-ride pass is available for $25.

Bicycle – Chicago is incredibly bike-friendly. Divvy is the city’s bike-sharing program. There are 5,800 Divvy bikes and you can get an unlimited day pass for $18.10 USD (for rides up to three hours each). You can also pay $1 USD to unlock a bike and then prices start at $0.18 USD per minute of your ride, depending on whether you take a bike or scooter. You can purchase these passes at station kiosks or via the app.

Taxis – Taxis are expensive here! Everything is meter-based starting at $3.25 USD and then $2.25 USD per mile. Skip the taxis if you can.

Ridesharing – Uber and Lyft are way cheaper than taxis and are the best way to get around a city if you don’t want to take a bus or pay for a taxi. I would definitely take them late at night over the bus too.

When to Go to Chicago

Spring (April to the end of May) and fall (September to the end of October) are both excellent times to visit Chicago, thanks to pleasant temperatures and fewer crowds.

Fall is especially nice, with daily temperatures averaging 60-70°F (15-21°C). You need to pack a sweater for this time of year, but tourist attractions are less crowded and hotel/hostel rooms are cheaper. The parks around the city are full of trees so it’s a great time to see the leaves changing. Chicago also has unique Halloween celebrations like Fall Fest and the Night of 1,000 Jack-o-Lanterns.

Summer (June-August) is peak season in Chicago. It’s hot, with temperatures reaching the mid-80s°F (high 20s°C), and tourist crowds are at their highest. Although it’s nice to take advantage of the weather, keep in mind that prices increase for accommodations and vacancies are low. August can be rainy, so pack a light rain jacket. This is the best time of year for attending outdoor events like the Millenium Park Summer Music Series.

Spring is a good time to visit as well. Temperatures average between 47-70°F (8-21°C), so you’ll want to pack layers. Outdoor activities begin to pick up and you can enjoy time on the river or a day watching a baseball game. There are flower shows and it’s cherry blossom season in the city as well.

Avoid visiting in winter unless you don’t mind some super cold days! The wind can be sharp during the winter months in Chicago. High temperatures average between 31-37°F (-1-3°C), but can feel much colder with the wind. If you want to do a lot of museum hopping or sightseeing indoors, you can save a lot of money on accommodations.

How to Stay Safe in Chicago

Although Chicago gets a bad reputation for crime and violence, it’s still a safe place to backpack and travel. Violent attacks tend to be confined to certain areas (especially where drug and gang violence are a problem) and rarely impact visitors. As a traveler, you’re likely to stick to the Loop, Wicker Park, Bucktown, and the Old Town, all of which are very safe.

Avoid Chicago’s South Side unless you want to see a White Sox game (the L Train stops right outside the stadium).

You might encounter petty crime, like theft, around famous tourist landmarks. Keep an eye on your belongings at all times, especially while taking public transportation.

If you’re approached by strangers asking for money or directions, use caution. This may be an attempt to draw you into an unwanted situation. Give brief, firm answers and move away to an area with more people.

At some attractions, like the Art Institute or the Field Museum, you may get approached by scammers who claim they can give you a cheaper tour inside. Avoid these “guides” as it’s all a scam. Read this post on common travel scams to avoid .

Solo female travelers should generally feel safe here but the standard precautions apply (never leave your drink unattended at the bar, never walk home alone intoxicated, etc.). For more specific tips, visit one of the numerous solo female travel blogs. They’ll be able to provide better tips than I can.

If you experience an emergency, dial 911 for assistance.

Always trust your gut instinct. Make copies of your personal documents, including your passport and ID.

The most important piece of advice I can offer is to purchase good travel insurance. Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. You can use the widget below to find the policy right for you:

Chicago Travel Guide: The Best Booking Resources

These are my favorite companies to use when I travel. They consistently have the best deals, offer world-class customer service and great value, and overall, are better than their competitors. They are the companies I use the most and are always the starting point in my search for travel deals.

• Skyscanner – Skyscanner is my favorite flight search engine. They search small websites and budget airlines that larger search sites tend to miss. They are hands down the number one place to start.
• Hostelworld – This is the best hostel accommodation site out there with the largest inventory, best search interface, and widest availability.
• Booking.com – The best all around booking site that constantly provides the cheapest and lowest rates. They have the widest selection of budget accommodation. In all my tests, they’ve always had the cheapest rates out of all the booking websites.
• Get Your Guide – Get Your Guide is a huge online marketplace for tours and excursions. They have tons of tour options available in cities all around the world, including everything from cooking classes, walking tours, street art lessons, and more!
• SafetyWing – Safety Wing offers convenient and affordable plans tailored to digital nomads and long-term travelers. They have cheap monthly plans, great customer service, and an easy-to-use claims process that makes it perfect for those on the road.
• LifeStraw – My go-to company for reusable water bottles with built-in filters so you can ensure your drinking water is always clean and safe.
• Unbound Merino – They make lightweight, durable, easy-to-clean travel clothing.
• Top Travel Credit Cards – Points are the best way to cut down travel expenses. Here’s my favorite point earning credit cards so you can get free travel!

Chicago Travel Guide: Related Articles

Want more info? Check out all the articles I’ve written on United States travel and continue planning your trip:

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A Snob’s Guide to Chicago

Is this list exhaustive? Maybe not. But it is highly opinionated, and that’s all that really matters.

I started visiting Chicago regularly after college, when my closest friends moved there. We went to the old Bistro 110 and felt very proud when we graduated to drinks at the Violet Hour and the Aviary, and then dinner at the Publican and Girl & the Goat (still favorites). There are things on this list I’ve loved for 30 years. Others became musts more recently. I also get a little help from my highly opinionated friends and family. Let’s call them the HOFs.

1. Check into the recently refreshed and perfectly located Park Hyatt Chicago. Ask for a lakeside room (on an upper floor). The Lake Michigan and Park Suites feel as if you are actually on the water.

2. “Walker Bros. for breakfast!” HOF and Chicago native Brooke Garber Neidich advises. “49ers pancakes, very crispy bacon, fresh-squeezed OJ.”

3. Take an architecture cruise. I like the Chicago Architecture Center River Cruise. I do this every time.

4. Have lunch at RL. Before Polo Bar in New York, before Ralph’s in Paris, there was RL in Chicago. It’s the OG.

5. Check into the Peninsula Chicago. Also right there on the Magnificent Mile. Have afternoon tea in the lobby and dumplings at the Shanghai Terrace. In winter ask about the skating rink!

6. The Langham (and its big, gorgeous rooms) is also a favorite.

7. Walk along Michigan Avenue to the Art Institute. (On the way, take your Kapoor Bean selfie.) The Thorne Miniature Rooms are a must, as is the Seurat that inspired Sondheim and Grant Wood’s American Gothic . The museum website has a great “what to see in an hour” guide.

8. ”The Field Museum of Natural History is also fabulous,” interjects HOF William Li. “The Hall of Jades! Go.”

9. “And the Fairy Castle at the Museum of Science and Industry!” Brooke says.

10. Riverwalk? Yes, says HOF Kate Chappell, news anchor for NBC Chicago. “End with sunset views at Tiny Tapp.”

11. Do the Frank Lloyd Wright Home and Studio tour in Oak Park. Ice cream at Petersen’s (around since 1919) afterward.

12. “Go see Robie House,” says my HOF niece and Chicago undergrad, Cayla, of Wright’s landmark. Reservations required. Afterward “get a Mediterranean omelet ­cafeteria-style at Valois, and try to sit at President Obama’s table, or have excellent Southern-inspired food at Roux.”

13. See a show at the Goodman Theatre. The hot ticket for 2024 will be Taylor Mac and Rob Ashford’s Midnight in the Garden of Good and Evi l (June 25–August­ 4).

14. And at the Steppenwolf. Laurie Metcalf will star in an as yet untitled show. It doesn’t get more Chicago than that.

15. And anything at the Lyric Opera.

16. “ The chorizo-stuffed bacon-wrapped ­medjool dates at Avec,” I say.

17. “A steak and a martini at Gene & Georgetti!” Brooke says.

18. “The tuna crudo and stracciatella appetizer at Rose Mary,” Cayla says. (I second this, and also a walk around the Fulton Market District.)

19. “The Hong Kong–style roast meats at Sun Wah BBQ,” William says.

20. “ The chicken pot pie, truffle bucatini, and the burger at Armitage Ale House,” Cayla says.

21. “Pasta at Monteverde. Any of them,” says basically everyone you will ever talk to.

22. “The thin crust pizza at Nancy’s in West Loop,” Kate says. That’s all I’ll say on the pizza matter.

23. The Kalamata chicken at the Athenian Room. It’s how Chicago theater royalty Carrie Coon and Tracie Letts celebrate their anniversary. (If that doesn’t matter to you, the rest of this list might not either.)

24. Wait in line for the Au Cheval burger. It’s a rite of passage. Same goes for dinner at Alinea. I have never been, and am ashamed.

25. Go to a Garrett Popcorn shop before you leave. Get tubs of the cheddar-and-caramel. Bring me some.

Editor-in-Chief Stellene Volandes is a jewelry expert, and the author of Jeweler: Masters and Mavericks of Modern Design (Rizzoli).

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Chicago, il.

Visit Chicago

Chicago travel guide video.

Discover sightseeing, shopping and sports in Chicago. Illinois’ largest city has a cultural scene that is as impressive as its skyline on the shores of Lake Michigan.

Within downtown Chicago’s Loop, visit galleries and restaurants. Snap a photo of Cloud Gate , known as The Bean , the iconic silver sculpture in Millennium Park. See the city unfold beneath you from the glass-bottomed ledge of Willis Tower.

Explore the neighborhood of Lincoln Park. Sunbathe on the namesake park’s public beaches, visit the animals in the Lincoln Park Zoo and discover exotic plants in the Lincoln Park Conservatory.

Ride the Ferris wheel in the waterfront Navy Pier district. Go shopping along the Magnificent Mile, the city’s famed shopping strip.

At Ernest Hemingway Birthplace and Museum, tour the childhood home of one of America’s most enduring authors. Visit Frank Lloyd Wright Home and Studio for a peek into the legendary architect’s life and work. Nearby, see the self-proclaimed “jewel” that Wright designed, Unity Temple.

Team spirit is strong in Chicago. Watch the Chicago Bears play on their home turf at Soldier Field. Root for a home run for the Chicago Cubs at iconic Wrigley Field.

Visit Chicago’s many outstanding museums. See ancient Mesopotamian carvings and art by Claude Monet at the Art Institute of Chicago. Learn about the city’s past at the Chicago History Museum. Check out the Apollo 8 spacecraft and other fascinating exhibits at the Chicago Museum of Science and Industry. See dinosaur bones and Egyptian mummies at Field Museum of Natural History.

Transport yourself to an African savannah, the Australian outback and the Arctic tundra at the Brookfield Zoo.

Explore beyond Downtown Chicago and visit Shedd Aquarium. Farther afield, the North Suburbs, West Suburbs and Aurora offer a break from the city bustle. Visit LEGOLAND in Schaumburg or see a polo match in Oak Brook. Spin through dozens of roller coasters and rides at Six Flags America in Gurnee.

Where to stay in Chicago

Downtown Chicago

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

Known for its great bars and fantastic lake views, there's plenty to explore in Lakeview. You can visit top attractions like Wrigley Field and Lake Michigan, and jump on the metro at Southport Station or Addison Station (Red Line) to see more of the city.

• Chicago Hotel Deals
• Vacation Rentals in Chicago

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Check Chicago hotel availability

Getting around chicago.

Public transportation in Chicago is comprehensive . Visitors can get just about anywhere in the city by combining various modes of transport, including the "L" train, CTA buses, taxis, rideshares, bicycle stations and walking. To visit Chicago's suburbs, the Metra Rail connects downtown with other Chicagoland hubs. This travel guide should provide more detailed answers concerning inter-city transportation options. Visit the Chicago Transit Authority (CTA) website. Browse Chicago rental cars .

Best time to visit

For warm temperatures that aren’t too hot, relatively minimal lines at popular attractions and a good range of festivals and cultural activities, try to visit Chicago between April and May or between September and October. With the highest temperatures reaching around 87 F (30 C), July is the hottest time to visit, but also one of the busiest. Avoid August if you don’t like rain, as this is the wettest month.

Popular places to visit

• Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

• McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

• Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

• Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Things to do

Odyssey lake michigan premier dinner cruise, chicago architecture center river cruise aboard chicago's first lady, reviews of chicago, 5/5 - excellent.

My first time was in Chicago and I love it definitely i I will visit again

2/5 - Disappointing

Had riots. Some locations i worked at i didnt feel safe. Going to get food was a challenge. But these are trying times.

I was born and raised in Chicago. It will always be my favorite city.

Being that most of everything was still closed the scenery was beautiful.

Loved going up to Chicago and would stay at this hotel again. I was called home do to a death in the family so I left a day early -- they were to send a refund to Expedia -- will that be credited to my charge card?? call me Rex Camp 317/507-4048

Read travel guides and advice on visiting Chicago

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• Places of interest
• Naval Base Great Lakes
• Soldier Field
• United Center
• Michigan Avenue
• Chicago Riverwalk
• Art Institute of Chicago
• Northwestern University
• Willis Tower
• Donald E. Stephens Convention Center
• University of Chicago
• Woodfield Mall
• Field Museum of Natural History
• Chicago Theatre
• Chicago Museum of Science and Industry
• Loyola University Chicago
• Gurnee Mills
• Allstate Arena
• University of Illinois Chicago
• Lincoln Park Zoo
• SeatGeek Stadium
• Schaumburg Convention Center
• John Hancock Center
• Merchandise Mart
• Water Tower Place
• LEGOLAND® Discovery Center
• Rosemont Theatre

A Beginner’s Guide to Chicago’s Underrated Beaches

Chicago has a little secret that most locals don’t share.

The beaches here are some of the best in the country. I may be biased as a Chicagoan, but I’ve traveled the globe as a travel writer, and my favorites are right here at home on Lake Michigan. The lakefront spans 18 miles, with more than two dozen free beaches offering spectacular views of the city. Each stretch has its own personality — and everyone seems to swear by a different favorite. Even better: Many of the beaches here have bars and restaurants attached, so you basically never have to leave. Here are some to try.

Kathy Osterman Beach

5800 N Lake Shore Drive

Located on the north end of Lake Shore Drive in Edgewater, this is truly a neighborhood gem. It’s quiet on weekdays, but on the weekends, it gets filled with locals who gather to play beach volleyball, swim and throw beach picnics. There isn’t parking, so you’ll have to walk, Uber or take the 147 bus here (it drops you two minutes from the beach). It’s worth it, as the water is very calm, and you can easily find a nice sandy spot to yourself. 

Montrose Beach

4400 N Lake Shore Drive

It’s all about the dogs at this pooch-friendly beach, but there’s way more on tap as well. Come here to kiteboard, watch the Navy Pier fireworks, go fishing, eat hot dogs, get some ice cream and drink beer, plus visit a bird sanctuary and two restaurants serving everything from tacos to traditional beach fare. Paddleboards and kayaks are available to rent, there’s a lifeguard on duty, and there’s even live music at the bar. There is parking, but if you want to score a spot, you should get there early in the day. The beach is large, so it can accommodate the masses who adore it, but those parking spots aren’t as plentiful. 

Oak Street Beach

1000 N Lake Shore Drive

One of the most popular beaches in Chicago, this is a see-and-be-seen sort of place. The free beach feels like a resort, although it’s smack dab in downtown Chicago. There are chairs to rent, concessions to eat, volleyball to play and bikes to ride. There’s even wifi, if you want to go that route (a better option: logging off and getting a beach massage under the tent from Coup De Main). When you get hungry, head to Oak Street Food and Drink, Whispers Restaurant or Boucher Brothers, all of which are fantastic summer options. This beach is on the smaller side, so be prepared to become friends with everyone around you, which is sorta the point of Oak Street Beach. It’s truly an Instagrammable scene. 

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12th Street Beach

1200 S Linn White Drive

This is such a great location, especially for anyone who wants to divide their day: the morning at the Museum Campus checking out the Adler Planetarium, Shedd Aquarium and Field Museum, and the other half just down the street at the 12th Street Beach. Make sure you come hungry: Del Campos is the beach restaurant, and they’ve got a full Mexican menu, along with the Chicago-style hot dog (because of course they do). This beach is one of the tiny but great ones. It’s not typically crowded, even on weekends, as it’s a little off the beaten path. And it doesn’t have volleyball or loud partying. If you’re looking for a quiet, cozy beach with fantastic tacos, calm water, families and parking, this one may become your fast favorite. 

Fullerton Beach

Post-pandemic, Fullerton Beach isn’t what it once was. While we were all sheltering at home, Lake Michigan’s rising waters took over the location, destroying it. Not to worry. Today, it’s not a traditional beach, but if you’re looking to relax without sand everywhere, then head here — because Chicagoans know how to make the best of every situation. It’s all grass and cement, so lots of people head here to relax in the sun, cycle and have picnics. It’s right on the water, but it’s more of a chill-out spot than a place to take a dip. But it has one of the best views of the city and of the lake, so it’s also a nice place for a photoshoot. When you get hungry or thirsty, you can still partake at Sandbox Beach Cafe, which has the best homemade guac in the area. Or head to Castaways, just down the lakefront on North Avenue Beach , where you’ll find live music and a big party scene (you’ll probably also spot some of the beachgoers who were getting their tan on at Fullerton). The frozen pina coladas, mai tais, margaritas and craft beers at the bar are worth a trip here on their own, but a beach where you don’t have to wipe yourself down at the end of the day? This is a true Chicago unicorn.

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The post A Beginner’s Guide to Chicago’s Underrated Beaches appeared first on InsideHook .

Travel | Chicago hotels among Michelin Guide’s first…

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Travel | chicago hotels among michelin guide’s first ‘keys’ awarded to us properties.

Last year, when World’s 50 Best issued its first global ranking of hotels, only two properties in the US made the cut: the Equinox and Aman New York hotels, both in Manhattan.

Now Michelin has arrived stateside, in its second-ever presentation of “keys”—a new system from the eponymous tiremaker that’s doling out one, two or three key emblems, like its restaurant stars but to the world’s worthiest hotels.

Out of more than 1,000 luxury hotels across the country, 11 were awarded three keys. The winners were all in California and New York, from Post Ranch Inn in Big Sur to Single Thread Inn in Healdsburg and the Whitby Hotel in Midtown. Aman New York, echoing its position on World’s 50 Best, was also included; Equinox, meanwhile, received no keys at all.

Importantly, keys were only distributed to hotels in seven primary markets across the US where the Michelin Guide also reviews restaurants: New York City, California, Chicago, Florida, Colorado, Atlanta and Washington, D.C. Michelin says next year’s ceremony will expand to include more of the US.One key denotes a “special” stay, two make it “exceptional” and three reflect hotels that are “extraordinary.”

Gwendal Poullennec, international director of the Michelin Guide, has described the criteria for these awards in highly subjective terms. Earlier this month he told Bloomberg that these most exceptional properties will be judged based off “the experience” alone. Rather than requiring them to adhere to certain definitions—like having a spa, pool or minimum staff-to-guest ratios—the hotel experience “has to be memorable and singular in a way that will give people a feel for local character,” he explained. At the awards ceremony, he built upon that sentiment. “We’re not a checklist of amenities,” he said.

This is still an improvement over other ranking systems, which rely on already-published articles by outside media or complimentary stays to produce their results; by contrast, Michelin has committed to independently paying for its hotel reviewers to stay at each property. In an interview after the ceremony, Poullennec went further, adding that multiple inspectors stay at each hotel, sometimes multiple times, before assigning keys.

“We have boots on the grounds, inspectors working the field in every country, leaving no stone unturned and also looking for discoveries, new openings, in order to be fully up to date in their recommendation,” Poullennec said in remarks during the key presentation.

The intimate US ceremony, held at New York City’s Museum of Art and Design, is the second such presentation by Michelin this month, with the first-ever awards being handed out to French hotels on April 8, in Paris. At that event, 24 hotels were awarded three keys, including five of Paris’ 12 “palace” hotels. And more such ceremonies are coming: Awards will be announced in Spain next week and in Italy on May 7, before heading to Japan in July.

To some US hoteliers, Michelin’s recognition holds outsize importance. In background conversations leading up to the event, owners of several new independent hotels in major cities held hope that earning multiple keys could help them compete with better-established luxury brands such as Aman, Rosewood or Ritz-Carlton. That may be the case for the boutique London-based Firmdale Hotels, whose two New York hotels, the Whitby and the Crosby Street Hotel, both earned three keys.

Others in more remote locations expected that any honor could help them lure talent—places like Twin Farms in Barnard, Vermont, or Blackberry Farm in Walland, Tennessee, for example. Unfortunately the prospect will have to wait.

It’s not that Michelin is the only designation that consumers can use to parse quality hotels. Walk into many of the key-awarded hotels, and you might see a Forbes’ five-star plaque—that honor was given to some 80 luxury hotels in the US in 2023, and American travel magazines dole out similar recognitions each year. But Michelin’s reputation spans much of the globe, in a way that the others do not.

“Our users say that when they are looking for places to stay, they will spend on average 10 hours on 10 different platforms to do so,” Poullennec said at the ceremony. “They’re at a loss. There is a demand for real recommendations and independent ones, that you can trust and go beyond brand labels, and that apply from one country to another—a global reference.”

Still, there are many skeptics. Michelin’s entry into the hotel market comes at a time when the company is looking for new revenue streams and attracting criticism for expanding its Michelin Dining Guides in a way that prioritizes destinations with big marketing budgets, even when they don’t have the restaurant quality to back it up.

The Atlanta Michelin Guide, for instance was sponsored by the local tourism board in a deal worth $1 million, but no restaurant in the city earned more than a single star. Its inclusion as one of the first destination in the hotel keys presentation will come as a surprise to luxury hotel afficcionados; the city is not widely known as a hub for luxury hotels, and only three hotels in the city were included, each with one key.

Pouillennec tells Bloomberg the overlap is because restaurant critics need places to sleep; that made it logistically feasible to prioritize these places. Although, as he told Bloomberg earlier in Paris, they’re not excluding the possibility of sponsored hotel guides in the future.

Also leading to skepticism about the awards is Michelin’s acquisition of Tablet Hotels, which took place in 2018 for an undisclosed sum; it’s a curated booking platform for luxury and boutique hotels that features some 6,000 hotels globally and around 950 properties in the US.

The technology gives Michelin a place where it can facilitate bookings for its recommended hotels, earn commissions from them, and also collect feedback from guests about their stays. As a result, some hoteliers have wondered whether Michelin has prioritized Tablet properties in its inspections; the company says reviews are completely independent and carried out by full-time employees, but adds that every hotel it recognizes is immediately bookable on its website.

“Nothing matters more than the independence of our recommendations,” Poullennec said.

In all, 124 hotels in the US were recognized with keys. Here is the full list of winners divided by market:

• The Beverly Hills Hotel, Dorchester Collection
• Post Ranch Inn, Big Sur
• SingleThread Inn, Healdsburg
• Hotel Bel-Air, Dorchester Collection, Los Angeles
• Auberge du Soleil, Auberge Resorts Collection, Rutherford
• Meadowood Napa Valley, St. Helena
• Canyon Ranch Woodside, Woodside

New York City

• Crosby Street Hotel
• The Whitby Hotel
• Aman New York
• Casa Cipriani New York
• L’Ermitage Beverly Hills
• The Maybourne Beverly Hills
• The Peninsula Beverly Hills
• Ventana Big Sur, an Alila Resort
• Bernardus Lodge & Spa, Carmel Valley
• The Stavrand, Guerneville
• Montage Healdsburg
• The Madrona, Healdsburg
• Montage Laguna Beach
• Rosewood Miramar Beach, Montecito
• Milliken Creek Inn & Spa, Napa
• Four Seasons Hotel San Francisco at Embarcadero
• The Battery, San Francisco
• Cavallo Point Lodge, Sausalito
• Pendry West Hollywood
• Chateau Marmont, West Hollywood
• North Block, Yountville
• Bardessono, Yountville
• Pendry Chicago
• The Langham
• The Peninsula Chicago
• Mayfair House Hotel & Garden, Miami
• The Setai Miami Beach
• Faena Hotel Miami Beach
• Four Seasons Hotel at The Surf Club, Miami Beach
• The Fifth Avenue Hotel
• The Carlyle, A Rosewood Hotel
• The Mark Hotel
• Hotel Barrière Fouquet’s New York
• Nine Orchard
• Pendry Manhattan West

Washington, D.C.

• Rosewood Washington, D.C.
• The Jefferson
• Stonehurst Place Atlanta
• The Candler Hotel Atlanta
• Hotel Clermont
• Four Seasons Resort Napa Valley, Calistoga
• Harbor House Inn, Elk
• Downtown LA Proper Hotel
• Soho Warehouse DTLA, Los Angeles
• The Aster, Los Angeles
• The Paramour Estate, Los Angeles
• The Prospect Hollywood, Los Angeles
• Stanly Ranch, Auberge Resorts Collection, Napa
• Pendry Newport Beach
• Dive Palm Springs
• Holiday House Palm Springs
• La Serena Villas, Palm Springs
• Sparrows Lodge, Palm Springs
• Rancho Caymus Inn, Rutherford
• 1 Hotel San Francisco
• Hotel Drisco, San Francisco
• Hotel San Luis Obispo
• San Luis Creek Lodge, San Luis Obispo
• El Encanto, A Belmond Hotel, Santa Barbara
• Casa Del Mar, Santa Monica
• Fairmont Miramar Hotel & Bungalows, Santa Monica
• Santa Monica Proper Hotel
• Shutters on the Beach, Santa Monica
• The Georgian, Santa Monica
• The Sea Ranch Lodge, Sea Ranch West
• Chamberlain West Hollywood
• Hotel 850 SVB, West Hollywood
• Palihouse West Hollywood
• Soho House Holloway, West Hollywood
• Sunset Tower Hotel, West Hollywood
• The Charlie, West Hollywood
• Chicago Athletic Association
• Nobu Hotel Chicago
• The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
• Viceroy Chicago
• Waldorf Astoria Chicago
• Hotel Jerome, Auberge Resorts Collection, Aspen
• The Little Nell, Aspen
• Mollie Aspen
• Clayton Hotel & Members Club, Denver
• Four Seasons Denver
• The Crawford Hotel, Denver
• Sonnenalp Hotel, Vail
• Four Seasons Vail
• Mandarin Oriental Miami
• Mr. C Miami – Coconut Grove
• 1 Hotel South Beach, Miami Beach
• Esmé Miami Beach
• Hotel Greystone – Adults Only, Miami Beach
• The Betsy – South Beach, Miami Beach
• Ette Hotel, Orlando
• Lake Nona Wave Hotel, Orlando
• The Ritz-Carlton Orlando, Grande Lakes
• Palihouse Hyde Park Village, Tampa
• The Tampa Edition
• 1 Hotel Brooklyn Bridge, Brooklyn
• Ace Hotel Brooklyn
• Wythe Hotel, Brooklyn
• 1 Hotel Central Park
• Baccarat Hotel & Residences
• Ritz-Carlton New York, Central Park
• Ritz-Carlton New York, NoMad
• The Beekman – A Thompson Hotel
• The Bowery Hotel
• The Greenwich Hotel
• The Hotel Chelsea
• The Ludlow Hotel
• The Peninsula New York
• The Wall Street Hotel
• Warren Street Hotel
• Pendry Washington DC – The Wharf
• Riggs Washington DC
• The Dupont Circle Hotel
• The Hay-Adams Hotel

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• The First MICHELIN Key Hotels: All the Keys in the United States

The MICHELIN Guide announces top honors for U.S. hotels in 2024.

Hotels NYC California Washington D.C. MICHELIN Keys

New York City by The MICHELIN Guide

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On April 24, 2024, the MICHELIN Guide revealed the brand new list of One, Two, and Three Key hotels in the United States. In this first ever announcement of MICHELIN Keys in the United States, hotels in Atlanta, California, Chicago, Colorado, Florida, New York, and Washington DC were eligible for the distinction. This announcement of the most outstanding hotels in the country comes four years into a comprehensive refresh of our hotel selection. The MICHELIN Guide now includes over 5,000 hotels across the world, and not a single one is simply a room for the night. These are places that significantly add to your experience as a traveler, each vetted and judged excellent in five categories: architecture and interior design, quality and consistency of service, overall personality and character, value for the price, and a significant contribution to the guest experience in a particular setting. Which brings us back to the Keys. The culmination of countless hours of evaluation by our team of experts, the Key hotels below represent the highlights of our broader selection. Like the MICHELIN Stars for restaurants, the MICHELIN Keys are our most outstanding hotels. In total, the 2024 MICHELIN Guide hotel selection in the United States includes 11 Three Key hotels, 33 Two Key hotels, and 80 One Key hotels. Want to know more about the MICHELIN Key? Here’s everything you need to know . Or, head below to look at all the Keys.

How To Look Through the List

Jump straight to the list or take a deeper dive into select key hotels..

Take a peek at SingleThread, the five room inn with Three Keys and Three Stars. Explore the one street in Chicago that leads to seven Key hotels. Or find out more the Cliff House suite at our only Three Key hotel in Big Sur, California. Subscribe to our newsletter for more like this.

Highlights of the United States 2024 Key Hotel List

The Three Key Club in New York City

Expect: The highest luxury and impeccable design in Soho, Midtown, and the Financial District. Within the small club of Three Key hotels in the United States, four make their home in New York City. The Aman New York (Midtown) and Casa Cipriani (the Financial District) both make use of glamorous Beaux Arts buildings, the former a gold-crowned skyscraper in Midtown, the latter a glamorously restored ferry terminal at the very southern tip of Manhattan. Each is a refuge: an elegant, painstakingly designed escape from bustling city life. Meanwhile, two Firmdale hotels round out the list of Three Key hotels in New York City. Each is a quintessential example of the style and execution of the group’s co-owner and interior designer, Kit Kemp. Click the links here to explore the whirl of colors and collage of art that define the Crosby Street (Soho) and the Whitby Hotel (Midtown). Also read: Every Three Key Hotel in Paris

Jewels on the Coast: Up and Down California

Its sheer breadth of size and variety means it’s no surprise to announce California as the state with the most Key hotels in America. Here, we’ll point you towards coastal gems like the sublime architectural achievements in Big Sur ( Post Ranch Inn and Ventana ), beachside luxuries in Santa Monica (in particular: the newly opened Georgian ), and wine country favorites like SingleThread and the Madrona . What we love: how each one of these hotels opens the door to the very best of their locations — and gives us a look at each setting through fresh eyes.

Across America: The Golden Age of Celebrity

Our French Keys bask in the tradition of ancient vineyards, stone chateaus, and historic palaces. In the United States, we see a different tradition. In Los Angeles, places like Chateau Marmont , the Paramour Estate , Sunset Tower , and the Charlie date back to guests and residents as illustrious as Clark Gable and Marilyn Monroe. These are spaces that play ingeniously with their history, even as they forge ahead with cutting-edge amenities and experiences. But it’s not just California. New York’s historic artist hotspot, the Hotel Chelsea , once hosted Bob Dylan and Andy Warhol. Today, it decorates every space with art donated by former residents. Look too to the Chicago Athletic Association , a former member’s club for 20th century business magnates and athletes — now among the city’s most impressive and vibrant hotels. Also read: Hollywood Glamor at the First Key Hotels in Los Angeles

Click below to jump to each distinction: 

The three key hotels.

California (Beverly Hills):  The Beverly Hills Hotel, Dorchester Collection California (Big Sur): Post Ranch Inn California (Healdsburg): SingleThread Inn California (Los Angeles):  Hotel Bel-Air, Dorchester Collection California (Rutherford):  Auberge du Soleil, Auberge Resorts Collection California (St. Helena):  Meadowood Napa Valley California (Woodside):  Canyon Ranch Woodside New York (NYC):  Aman New York New York (NYC):  Casa Cipriani New York New York (NYC):  Crosby Street Hotel, Firmdale Hotels New York (NYC):  The Whitby Hotel, Firmdale Hotels

NEW: New York by The MICHELIN Guide – expert insights on where to dine, stay and explore

The two key hotels.

California (Beverly Hills): L'Ermitage Beverly Hills California (Beverly Hills): The Maybourne Beverly Hills California (Beverly Hills): The Peninsula Beverly Hills California (Carmel Valley): Bernardus Lodge & Spa California (Big Sur): Ventana Big Sur California (Guerneville): The Stavrand California (Healdsburg): Montage Healdsburg California (Healdsburg): The Madrona California (Laguna Beach): Montage Laguna Beach California (Montecito): Rosewood Miramar Beach California (Napa):  Milliken Creek Inn & Spa California (San Francisco):  Four Seasons Hotel San Francisco at Embarcadero California (San Francisco):  The Battery California (Sausalito):  Cavallo Point Lodge California (West Hollywood): Chateau Marmont California (West Hollywood):  Pendry West Hollywood California (Yountville):  Bardessono California (Yountville):  North Block Washington D.C.:  Rosewood Washington, D.C.   Washington D.C.:  The Jefferson Florida (Miami):  Mayfair House Hotel & Garden Florida (Miami Beach):  Faena Hotel Miami Beach Florida (Miami Beach):  Four Seasons Hotel at The Surf Club Florida (Miami Beach):  The Setai Miami Beach   Illinois (Chicago): Pendry Chicago Illinois (Chicago):  The Langham, Chicago Illinois (Chicago):  The Peninsula Chicago New York (NYC): Hotel Barrière Fouquet's New York New York (NYC):  Nine Orchard  New York (NYC):  Pendry Manhattan West New York (NYC): The Carlyle, A Rosewood Hotel New York (NYC): The Fifth Avenue Hotel New York (NYC):  The Mark Hotel

The One Key Hotels

Washington D.C.

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New Borealis Amtrak Train Connects St. Paul to Chicago

Beginning May 21, the new train will stop in Wisconsin Dells, Milwaukee, and more on the way to Chicago, starting at $41 one way.

by Saija Maki-Waller

May 2, 2024

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Amtrak Train

Currently there’s only one Amtrak to Chicago from the Twin Cities, but the new Borealis route from the railroad company will double the daily train options for travelers, making stops in Red Wing and Winona before cruising through Wisconsin. 

For those who have made it in the Twin Cities without a car, wanting to skip the drive, or are looking for a fun and affordable way to sightsee, the Amtrak route opens up new possibilities for regional travel. Starting May 21, hop on the train midday at Union Depot in St. Paul, with coach prices for the 7 hour and 24 minute ride starting at $41 one way. 

The state-sponsored trains will feature wide reclining seats and, thankfully, no middle seat. Enjoy an on-board café and views of the Mississippi River from the Twin Cities to La Crosse, Wisconsin. 

“A second daily passenger rail service connecting St. Paul to Chicago via Milwaukee is a welcome addition to our transportation system, providing more choices and travel flexibility for passengers,” said Nancy Daubenberger, commissioner from the Minnesota Department of Transportation in a statement on the Amtrak website. “We look forward to continuing these partnerships as we work toward further building out passenger rail options in the Midwest.”

Until the Borealis line officially opens, you can still move from St. Paul to Chicago with Empire Builder, another Amtrak route that rides through the Pacific Northwest. Take it to Chicago or take it all the way to Seattle. 

Trains are one of the most environmentally conscious modes of transportation, putting out less greenhouse gas emissions than roadways and airways. With the expansion of passenger trains in the midwest, consider the Borealis a new and picturesque way to get to and from the Windy City.

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