downtown chicago tour

THE 10 BEST Tours & Activities in Downtown / The Loop (Chicago)

Tours & activities in downtown / the loop.

• Sightseeing Tours
• Historical & Heritage Tours
• Cultural Tours
• Up to 1 hour
• 1 to 4 hours
• 4 hours to 1 day
• 5.0 of 5 bubbles
• 4.0 of 5 bubbles & up
• 3.0 of 5 bubbles & up
• 2.0 of 5 bubbles & up
• Chinese (Traditional)
• Likely to Sell Out
• Special Offers
• The ranking of tours, activities, and experiences available on Tripadvisor is determined by several factors including the revenue generated by Tripadvisor from these bookings, the frequency of user clicks, and the volume and quality of customer reviews. Occasionally, newly listed offerings may be prioritized and appear higher in the list. The specific placement of these new listings may vary.

1. Chicago Architecture River Cruise

2. Chicago River 90-Minute History and Architecture Tour

3. Chicago River 45-Minute Architecture Tour from Magnificent Mile

4. Chicago Architecture Center River Cruise aboard Chicago's First Lady

5. Chicago: Gangsters and Ghosts Walking Tour

6. Skydeck Chicago Admission Ticket

7. Lake Michigan Sunset Cruise in Chicago

8. Chicago River Boat Architecture Tour

9. Insta Walk and Polaroid Photoshoot in Chicago

10. Big Bus Chicago Hop-On Hop-Off Sightseeing Tour

11. Chicago Favorites Food and Walking Tour

12. Chicago Crime and Mob Bus Tour

13. Chicago in a Day: Food, History and Architecture Walking Tour

14. 360 CHICAGO Observation Deck Admission

15. Flyover in Chicago

16. Chicago CityPASS®

17. Chicago River Cocktail Cruise

18. Chicago Gangster and Food Walking Tour

19. Chicago Buffet Lunch Cruise on Lake Michigan

20. Chicago Lake and River Architecture Tour

21. Chicago Craft Brewery Barrel Bus Tour

22. Chicago Walking Food Tour With Secret Food Tours

23. Lake Michigan Skyline Cruise in Chicago

24. 2-Hour Guided Segway Tour of Chicago

25. Chicago's Secret Interiors Architectural Tour

26. Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

27. Chicago City Minibus Tour

28. Field Museum of Natural History Admission Tickets

29. Blue Man Group at the Briar Street Theater in Chicago

30. Chicago Architectural River Cruise

What travelers are saying.

• United States

35 Fun & Unusual Things to Do in Downtown Chicago, Illinois

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Thousands of tourists make their way to Chicago every year, and for good reason. The “windy city” has plenty to offer in the form of great architecture and a stunning skyline filled with skyscrapers, world-class museums, a growing craft beer culture, and a shoreline that mixes modern waterfront areas with miles of beaches and iconic landmarks.

The list of places to visit in Chicago is long and exciting and covers everything from amazing food to an exciting cultural scene.

No matter why you’re visiting, though, there are plenty of fun things to do in Chicago – so many, in fact, that we are focusing our list on the best things to do in Downtown Chicago , a 35-block area famous for its vibrant urban atmosphere.

1 – Take a sightseeing river cruise

There’s no better way to admire the city’s great architecture than from the water – and the Chicago River offers the perfect opportunity to relax on board a cruise and enjoy Chicago’s iconic skyline.

Most cruises depart from Navy Pier and for 60-75 minutes (depending on which cruise you choose) will take you to see many of the city’s most famous landmarks, including the Tribune Tower, Marina City, and the John Hancock Center skyscraper.

You’ll sail under historical bridges, be able to listen to a live narration, and discover all three branches of the Chicago River as you learn about the buildings that helped shape the city.

Drinks are available for purchase and cruises depart several times a day, so you can choose the time more convenient for you.

• boat tours in Chicago

Read more about the best Chicago architecture boat tours

2 – Soak up some sun at Millennium Park

Covering almost 25 acres, Millenium Park is much more than just a green space in the heart of Chicago. Filled with interesting art and great attractions, the park has become a gathering point and the place to be for major annual events (like the lighting of the city’s Christmas tree every year).

Crown Fountain is perhaps the best-known spot in the park – a video tower sculpture that displays videos as it spouts waters into the reflecting pool next to it.

The park’s Jay Pritzker Pavilion, a massive outdoor amphitheater, is home to the Grant Park Symphony Orchestra and Chorus and holds musical series, summer concerts, and performing arts events.

Another favorite in the park is Cloud Gate (aka The Bean), a massive 10 m× 13 m×20 m stainless steel sculpture that reflects a distorted Chicago on every inch of its surface.

Near the northwest end of the park, there’s Wrigley Square, best known for its Millenium Monument, a fun semi-circle of 12-meter-tall Roman-style columns popular for photo opportunities and events.

3 – Get your culture fix at one of the many art museums in Chicago

Chicago is home to some incredible museums, and your list of things to do in Downtown Chicago should certainly include some of them.

With a world-class collection of over 300,000 pieces, The Art Institute of Chicago is a good place to start. If you’re still hungry for more great art, try the Museum of Contemporary Art , where the collection focuses on post-WWII artists.

With a massive collection of work by Ansel Adams, portraitist Julia Margaret Cameron, and street-photography pioneer Julia Margaret Cameron among many other famous names, the Museum of Contemporary Photography  is a great place to spend a couple of hours discovering the great American photographers of the past century.

Housed in a former private mansion, the Richard H. Driehaus Museum is an homage to the stunning decorative arts of the past two centuries. In addition to original art nouveau items, the home features lots of Tiffany glass and artworks and marble sculptures.

For a unique experience, it’s hard to beat the WNDR Museum , an immersive experience that features exhibits like an Infinity Mirror Room, audio-visual installations, and optical illusions.

Read more about the best museums in Chicago

4 – Enjoy the waterfront views at Navy Pier

The 1,000-meter-long pier has become one of Chicago’s most recognizable and popular destinations. Sitting right on Lake Michigan and home to a number of attractions, shops, and restaurants, the pier is a busy place no matter the season.

Outdoor attractions include everything from remote control boats to a drop tower, an old carousel, and a state-of-the-art Centennial Ferris Wheel that will take you over 60 meters up into the air for breathtaking 360-degree views over Chicago and Lake Michigan.

Other attractions include a 370-square-meter maze, a one-acre botanical garden, and the Chicago Children’s Museum. On rainy days, an IMAX theater and the Chicago Shakespeare Theater offer great indoor options as well.

Even if you don’t visit any of the attractions, the pier itself is a great place for a walk and often features outdoor art installations and live music in summer. The 45-meter Schooner Windy tall ship departs from Navy Pier and offers not only great views of the shoreline but also a choice of a Pirates-inspired sail or a sunset sail.

• Navy Pier Centennial Wheel tickets

5 – Say hi to marine creatures big and small at the Shedd Aquarium

Home to over 30,000 animals, the Shedd Aquarium is divided into major zones like Caribbean Reef, Amazon Rising, Polar Play Zone, and Waters of the World.

Learn about the animals inhabiting Chicago’s local waters, say hello to rescued green sea turtles, meet red-bellied piranhas and green anacondas, and pet giant rays. Or head to the underwater viewing area to come face to face with beluga whales, dolphins, and penguins.

A 4D theater inside the aquarium shows water-inspired films like Sea Monsters and Ice Age. There are also special temporary exhibits focused on beautiful marine creatures, the unique Australian Lungfish, sharks, and American alligators.

6 – Discover Chicago’s past with a gangsters and crime tour

The Windy City is historically known for being home to notorious mobsters during the 1920s Prohibition Era. Al Capone once called Chicago home and ran an underground gambling and bootlegging “industry” that was worth millions of dollars.

Today, plenty of tours will take you to the hot spots of Prohibition-era mobster activity, showing you the criminal underworld of Chicago and giving you a glimpse of how big names like Capone, the Untouchables, and John Dillinger forever changed the city.

Both walking and bus tours are available, and both come with a history-savvy guide who will take you to the most important location of Chicago’s criminal past. Visit the place where the St Valentine’s Day Massacre took place, stop by an old gangster headquarters, see where Al Capone used to carry out business and also where he went for fun, and stop by Harry Caray’s Italian Steakhouse to visit the secret vault once used by Frank Nitti.

Gangsters and Ghosts tours are also available, where you’ll get a peak into Chicago’s most haunted places, including the Palmer House and Death Alley.

• gangsters and crime tours

7 – Take the kids to the Chicago Children’s Museum

At the top of things to do in Downtown Chigaco if you have kids is this interactive museum located at the popular Navy Pier. At almost 8,000 square meters, it’s one of the largest children’s museums in the country.

Four floors of hands-on exhibits are divided into three age groups, including babies and toddlers, ages 4-8, and ages 9 and up. This means everybody gets a chance to have fun learning for hours on end at the Chicago Children’s Museum .

Exhibits include everything from boats and climbing corners to an art studio, a kids’ town, a dinosaur area (complete with an excavation pit), and a tinkering lab where young scientists can explore technology, math, and engineering concepts.

8 – Catch breathtaking panoramic views from the 360 Chicago Observation Deck

There’s no better place to catch breathtaking 360-degree views of Chicago’s skyline than from the top of the 360 Chicago Observation Deck.

Set 94 stories up in the air, near the top of the John Hancock Center skyscraper, the observatory offers bird’s-eye views of many city landmarks as well as the lakefront shoreline and it’s definitely one of the best things to do in Downtown Chicago.

Just getting to the observatory is thrilling (you’ll be riding one of the fastest elevators in the country), but the real excitement here is TILT, a thrill ride in the form of a glass platform that tilts forward at a 30-degree angle so you can get the best downward-facing views from 1,000 meters up in the air.

The observatory is also home to the Architect’s Corner Café and Bar and an open-air SkyWalk.

• 360 Chicago Observation Deck tickets

9 – Discover local delicacies with a food tour

Chicago has its share of special local foods – perhaps the most famous ones being the Chicago deep-dish pizza or Chicago-style pizza and the iconic Italian beef sandwich – and the best way to experience them is through a food tour.

Stroll through the streets of Chicago with an expert guide and discover the best spots to taste a number of foods. Learn about the history of the city as you walk past famous landmarks like the Chicago River and Millennium Park and discover great architecture and street art.

Sink your teeth into some deep-dish pizza, sip a local beer, taste a Chicago-style hot dog, and enjoy original Italian pastries. You can even choose special food tours like a 2.5-hour Taste of Chinatown walking tour or a half-day tour exploring both the food and the architecture of Chicago. There’s even a donut tour for a mouth-watering sweet experience at some of the best donut shops in the city.

• food tours in Chicago

10 – See Chicago like never before from the Willis Tower Skydeck

The 108 stories tall Willis Tower is best known for its observatory. It’s not only the tallest Skydeck observatory in the country but also one of Chicago’s most popular attractions.

Here, visitors can step into retractable glass balconies – essentially glass boxes with a glass floor extending more than 1 meter out from the building.

Not only can you look 400 meters straight down over the streets below, but also get 360-degree views over Lake Michigan and spanning four states on clear, sunny days. Don’t miss out on this thrilling experience when in Chicago!

• Willis Tower Skydeck Chicago tickets

Hot tip: Cheap Skydeck Chicago Tickets – How to Save up to 20%

11 – See the city’s most famous buildings with an architecture tour

Chicago’s most iconic buildings sit near the river – and there’s no better way to enjoy them than with an architecture river cruise tour. Jump onboard and let your expert guide introduce you to landmark buildings as you cruise along all three branches of the Chicago River.

You’ll pass by the 36-floor neo-Gothic skyscraper Tribune Tower, the Rookery Building (Chicago’s oldest standing high-rise), and the Wrigley Building, a stunning 1920s skyscraper with a bright white facade. You’ll also see the Chicago Water Tower, listed on the National Register of Historic Places and once used to pump water from the lake.

Would you rather try an architectural walking tour of Chicago? For a shorter, self-guided architecture tour, head to the 2 km-long Chicago Riverwalk .

Otherwise, try The Loop route, which takes you through the best of Downtown Chicago art-deco buildings, where you’ll step inside the dazzling lobby of the Rookery Building, see the vibrant facade of the Chicago Board of Trade, and marvel at the beauty of buildings right out of the roaring 1920s.

Some of these walking tours will also take you to the Chicago Cultural Center (famous for its Tiffany glass dome) and the Chicago Architecture Center , where you’ll have a chance to learn more about the city’s architectural history.

• architecture tours in Chicago

12 – Visit the stunning Holy Name Cathedral

This breathtaking Gothic Revival cathedral was built after the Great Chicago Fire of 1871 destroyed two of the main churches in the city.

The result is an architectural marvel that mixes dark wood with lots of stained glass and details like massive bronze doors, 21-meter-tall ceilings, and a number of sculptures and castings depicting the apostles and Old Testament scenes.

The church is home to two pipe organs often used during mass and an overall design that focuses on the “Tree of Life” theme of Biblical salvation.

The Holy Name Cathedral is open to visitors during the day if you just want to admire its beauty and take some photos.

13 – Walk the historical Michigan Avenue

Running from the shore of Lake Michigan all the way through the city, Michigan Avenue was once primarily residential. Over the years, the road has been extended north of the Chicago River and now crosses over the Michigan Avenue Bridge (officially named the DuSable Bridge), connecting Chicago’s south side and north side.

Today, a walk down Michigan Avenue is one of the must-do things in Downtown Chicago. Home to some of the city’s most important attractions – including Millennium Park and The Art Institute of Chicago – Michigan Avenue has become an attraction in itself. Part of the reason for that is the stretch of the avenue known as the Magnificent Mile .

Flanked by skyscrapers and similar to Fifth Avenue in New York, the Magnificent Mile is filled with luxury shops, restaurants and 5-star hotels, and a number of Chicago landmarks. During the Christmas season, over a million lights are used to decorate the trees lining up the avenue.

• walking tours in Chicago

14 – See the world’s largest dinosaur at the Field Museum of Natural History

With a collection of over 24 million objects, the Field Museum of Natural History (FMNH) is one of Chicago’s most impressive museums. The collection covers everything from fossils and meteorites to ancient civilizations, creepy creatures, gemstones, and biodiversity.

The main attractions here are, without a doubt, the dinosaurs – which include SUE (the most complete T.rex ever found) and Titanosaur Máximo, the largest dinosaur that ever lived at 37 meters long and almost 9 meters tall.

There’s also a 3D theater, a kid-friendly PlayLab, and an exciting Egyptian exhibit complete with mummies, a 4,000-year-old boat, and an ancient burial chamber.

The FMNH is part of the Museum Campus, a 57-acre waterfront park that’s also home to a number of other attractions such as the Adler Planetarium, the multi-purpose Soldier Field stadium, the Shedd Aquarium, and America’s largest convention space at McCormick Place.

• Field Museum of Natural History tickets

15 – Catch a game at the United Center

This multi-purpose indoor arena is the permanent home of the National Basketball Association’s Chicago Bulls and the National Hockey League’s Chicago Blackhawks. Other sporting events, including NCAA basketball, professional wrestling, and mixed martial arts tournaments are sometimes held at United Center as well.

With a capacity of over 20,000, the arena has also become a popular venue for concerts – over the years, everybody from Paul McCartney to Lady Gaga to the Rolling Stones has performed here.

The arena features a number of statues representing some of the most famous house players, including Michael Jordan and Blackhawks legend Bobby Hull.

If you’re visiting Chicago during the pre-season (which starts in October), you should be able to get tickets last minute to cheer for the local team.

16 – Discover the city with a hop-on hop-off bus tour

Save time and money and see all the city’s top sights with a hop-on hop-off bus tour. You’ll avoid headaches and trying to figure out an itinerary – just jump on board and get off at the stop of your choice to explore and take some photos.

When you’re ready, just get back on the open-top, double-decker bus and continue on your journey as you listen to the audio commentary and learn more about Chicago’s history and culture.

The bus takes you on a two-hour loop that includes 11 stops, such as the Navy Pier, the 360 Skydeck, Museum Campus, and the Chicago Riverwalk.

If you want to see a different side of the city, grab a seat on the Big Bus Chicago Night Tour , a 75-minutes non-stop tour that takes you to see the most stunning landmarks as the city lights turn on.

• bus tours in Chicago

17 – Celebrate the world of sports at the Chicago Sports Museum

The 2100-square-foot Chicago Sports Museum not only houses a massive collection of sports memorabilia, but it’s also home to interactive experiences that will make you feel like your favorite sports stars are right there with you.

Learn about the evolution of baseballs, test your vertical jump against the giants of basketballs, see game memorabilia, and explore the history of Chicago baseball. You can jump into a racing car simulator and learn about the superstitions and legends of the sports world.

You can even see the original Sports Almanac prop from the movie “Back to the Future II,” which predicted the Chicago Cubs would win the World Series in 2015. The Cubs, which had not won a World Series since 1908, actually won the title in 2016 – just a year off from what the movie predicted.

18 – Trick your mind at the Museum of Illusions

Stop by this museum to discover a great collection of magic and trickery exhibits that will both confuse you and amuse you! Get ready for lots of interactive fun created with paint, holograms, and clever design.

Over 80 mind-bending illusions will keep both kids and adults busy for a couple of hours – Step into a spinning vortex tunnel, walk into rooms that defy the laws of physics and practice some anti-gravity moves, come face-to-face with a bottomless pit, and shrink yourself to tiny sizes.

You’ll find plenty of perfect selfie opportunities here; each exhibit even has a mark to show you where to stand for the best photos!

• Museum of Illusions tickets

19 – Take a Segway tour around Grant Park

Looking for things to do in Downtown Chicago when you only have a couple of hours to fill? You can discover Chicago’s beautiful lakefront on a fun Segway tour as you learn about the area’s history and famous landmarks.

Most tours start at the Buckingham Fountain in Grant Park and then bring you closer to popular attractions like Lake Michigan and the city skyline, Museum Campus, and Millennium Park.

Don’t worry if this is your first time riding a Segway! Your tour guide will guide you through the basics before you set off on your adventure. There is nothing like seeing the city on a Segway tour – you’ll be able to cover a lot more ground than you would walking and have lots of fun in the process!

• segway tours in Chicago

20 – Spend an afternoon discovering Lincoln Park

Chicago’s largest park has so much to offer, you’d need an entire day to truly explore it all. Over 1,200 acres of green space serve as home to nature reserves, recreational facilities including a golf course and a skate park, and a number of public beaches that offer great swimming and boating facilities. North Avenue Beach is particularly popular and offers plenty of space for lounging shoreside and water activities.

Perhaps the most famous attraction here is the Lincoln Park Zoo , a 35-acre space home to over 1,000 animals. The Conservatory is another big draw, home to displays of everything from giant palms to an orchid room. The Peggy Notebaert Nature Museum is a nice complement, with a butterfly house and exhibits about the ecosystem of the region.

If you’re up for learning more about Chicago and American history, the Chicago History Museum offers a great look into the growth of the city, chronicles Lincoln’s assassination, and provides a number of exhibits for kids.

21 – Enjoy the magic of Lake Michigan

The largest (by area) of the five Great Lakes, Lake Michigan attracts thousands of visitors every year, who mostly come here for water sports like sea kayaking, kitesurfing, and yachting.

A number of wide and busy beaches line up the shoreline, with Ohio Street Beach offering convenience (it’s very close to Navy Pier) and lots of open space to lounge. Winter visitors often stop by the fascinating phenomenon of ice volcanoes forming on the lake.

Boat tours are a great way to discover the beauty of the lake. You can choose between a relaxing skyline or a brunch cruise. Or end the day with a relaxing dinner cruise where you can indulge both your eyes and your taste buds with a great all-you-can-eat buffet and onboard entertainment with DJ music.

Adrenaline lovers can choose an exciting speedboat ride that takes you on an architecture tour along skyscrapers and old bridges and ends with a massive fireworks display. There are also ferries that take passengers to different nearby islands for sunbathing in a bit more privacy.

If you’d rather stay on land, the 29km-long Lakefront Trail is a great way to explore the shoreline – no matter if you’re biking or hiking.

• Lake Michigan tours

22 – Get inspired at the American Writers Museum

The only museum in the country completely dedicated to American writers and their work, this quirky but interesting space offers exhibits on the work of novelists, poets, journalists, and even humor writers. There’s even a special section dedicated to the work of local Chicago writers.

Interactive stations allow visitors to play videos and sounds and even to activate scents connected to important literary works.

See how American writers from the 1600s and 1700s started to develop their own style away from European influence, what readers were choosing to read for fun through the centuries, and the writing habits of famous authors.

The American Writers Museum also hosts temporary exhibits and organizes special “meet the writers” evenings.

23 – Check out Soldier Field Stadium

The multi-purpose Soldier Field Stadium is home to the NFL’s Chicago Bears and the Chicago Fire FC soccer team, but it has also hosted a number of other events, including games for the Special Olympics, rallies from famous figures like Martin Luther King Jr, and the occasional hockey game.

The stadium can sit over 61,000 people, making it perfect for large events and shows. Concerts held here have included everybody from Barbra Streisand and Paul McCartney to The Rolling Stones, Madonna, and Jay-Z.

The 1924 stadium lost its National Historic Landmark designation in 2006 after an extensive renovation that modernized the space and added environmentally sustainable details.

24 – Visit The Second City, Chicago’s best comedy club

If you’re looking for things to do in Downtown Chicago once the sun sets, this one is a must. Chicago’s oldest improv theater takes its name from one of the city’s old nicknames. Back in the early 20th century, Chicago earned the second-place slot in an ongoing rivalry between Chicago and NYC as the best metropolitan area.

While this might sound like a loss, Chicago has embraced its nickname in a fun way – and you can see just that when you visit The Second City premier comedy club.

The club served as the starting point for many famous comedians – including Alan Alda, Mike Myers, and Bill Murray – and a number of well-known performers still take to the stage here regularly. Stop by any night of the week for a laugh-out-loud good time with live shows starting at 7 pm.

25 – Spend the day at Maggie Daley Park

The 20-acre Maggie Daley Park , located near Lake Michigan, is best known for its many activities and features available.

The biggest attraction is the half km long ice skating ribbon, which runs along one side of the park and offers slight changes in elevation for some fun challenges. During the summer, the space is used as a rollerskating area.

Two rock-climbing structures with a maximum height of 12 meters welcome both beginners and experienced climbers and offer both bouldering and lead-harnessed climbing.

For family-friendly fun, there’s an 18-hole miniature golf course, tennis courts, and an Alice-in-Wonderland inspired “play garden” filled with lots of water features, climbing spaces, slides, and bridges for kids of all ages.

26 – Take a helicopter tour over the Chicago’s skyline

Want to see Chicago’s beautiful architecture and green spaces from up above? A helicopter tour is the best way to do just that! Soar over Downtown Chicago, past the Willis Tower and over famous sights like Wrigley Field, the Navy Pier, and the Chicago River.

The 15-minute ride will allow you to capture stunning photos of the city in a Bell 206, turbine-engine helicopter. You’ll feel the rush of the flight combined with the excitement of seeing iconic landmarks like never before.

Private 45-minute scenic flights are a great choice if you’re traveling with your own group and want some privacy and out-of-this-world views of Chicago.

• helicopter tours in Chicago

Read more about helicopter tours in Chicago – which one is the best?

27 – Attend a performance of the Chicago Symphony Orchestra at Orchestra Hall

The historical Orchestra Hall at the Symphony Center has been home to the Chicago Symphony Orchestra and the Chicago Symphony Chorus for many years.

While the building retains many original architectural details dating back to 1904, the Orchestra Hall was extensively renovated in the 20th century to improve acoustics, re-organize seating spaces to avoid blind spots, and add rehearsal spaces and features like a cafe and better lighting.

The hall’s concert series includes a mix of classical masterpieces and unique new shows, including piano concerts, kid-friendly programs, and acclaimed guest conductors. There are also unique movie experiences throughout the year where you get to enjoy classic films — from Amadeus to The Princess Bridge to Harry Potter — on giant screens as the orchestra performs the film’s score live.

28 – Grab a drink or two during a beer-tasting tour

Chicago has become a great destination for craft beer, and you can try several of them in one single evening when you book a special guided tour of some of the best breweries in town – you’ll get a chance to see the brewing process and enjoy plenty of beer samples along the way.

For a truly unique experience, grab a seat on the Chicago Craft Brewery Barrel bus tour. Visit a number of craft beer breweries onboard a bus shaped like a giant barrel reminiscent of those used during the 1920s Prohibition Era.

Want to explore on your own? There are plenty of breweries in Downtown Chicago that are worth a visit, including The Moody Tongue brewery with its barrel-aged brews, Motor Row Brewing and its unique beers (don’t miss their Blonde Belgian honey wheat brew), and Rock Bottom Restaurant & Brewery , one of the original breweries in Chicago.

Miller’s Pub , one of Chicago’s oldest late-night spots, offers great comfort food and an old-school vibe perfect for grabbing some drinks.

• beer tasting in Chicago

29 – Indulge your inner space explorer at the Adler Planetarium

Despite its name, the Adler Planetarium is also an astronomy and astrophysics museum. Built in the 1930s as the first planetarium in the country, the Adler has become synonymous with the quest for understanding the universe.

Visitors should stop at the planetarium’s Doane Observatory first, which is open on select Wednesdays nights, before heading into the main building to explore more. There, you can catch a show at the massive Grainger Sky Theater or the Samuel C. Johnson Family Star Theater, which specializes in 3D shows.

The museum includes a number of exhibits dedicated to the history of stargazing, the Chicago night sky, the missions to the moon (which includes the original Gemini 12 spacecraft), and our solar system.

Visitors can take photos with some of NASA’s rovers, learn through interactive stations, and take a look through a 17th-century telescope.

30 – Test your wits at The Escape Game Chicago

Do you have what it takes to find clues, solve puzzles and beat the clock? You have just 60 minutes to test your problem-solving skills and unlock the room – and you will require great teamwork and a sense of adventure to make it happen!

Rated the #1 Escape Room in the country with over 6,000 reviews on Google, The Escape Game Chicago offers five scenarios to choose from. Become a secret agent in a mission around a mysterious spice market, travel back in time to the Gold Rush era, fix your spaceship that just crash-landed on Mars, or find a stolen Monet painting.

Expert players can try their luck in the Prison Break room, considered one of the hardest escape rooms ever designed.

• escape rooms in Chicago

Hot tip: Challenge your problem-solving skills at an escape room, highlighted as one of the best indoor activities in Chicago for groups

31 – Catch some late-night tunes at Buddy Guy’s Legends

Considered one of the best blues club in the country, Buddy Guy’s Legends prides itself for bringing the best blue acts and some of the world’s most talented musicians under one roof. Buddy Guy himself – a blues guitarist and singer who’s won eight Grammy Awards – performs at the club every January to a sold-out space.

Live shows are available seven nights a week but you can also stop by just to admire the amazing collection of personal items that cover the walls. From rare photos and artwork to Keith Richards and Eric Clapton’s personal guitars, there’s plenty to discover here.

32 – Grab a seat to the most exciting shows at the Chicago Theatre

The Chicago Theatre started life as an opulent movie theater in 1921 and is now considered one of the last surviving “grand movie palaces” in the country. The theater had space for a large live orchestra to accompany silent films, and an opulent interior that included stunning murals painted on the walls.

After years the neglect in the 1970s and a major restoration in the late 1980s, the Chicago Theatre now serves as a stage for everything from music concerts to comedy shows to stage plays.

Part of the restoration included revitalizing the theater’s interior and bringing back to life the grand lobby and staircase, Tiffany stained glass windows, and grand Wurlitzer pipe organ, one of the oldest of its kind still around.

• Chicago Theatre tickets & tours

33 – Connect with history at the International Museum of Surgical Science

Chicago’s most unique museum is home to a collection of items and exhibits focusing on the history of Eastern and Western medicine. From very early drawings and medical equipment to photographs, skeletons, and artifacts chronicling the breakthroughs and failures of medicine through the centuries, this is a museum that will awe, inspire and shock.

Special exhibits are dedicated to the 19th-century apothecary, polio and the use of the iron lung, pathology, the science of sight, and the history of dentistry.

The International Museum of Surgical Science also organizes temporary exhibits that focus on specific areas of medicine and history, such as a look into the deadly medicine of the Nazis, the world without polio, how the world has changed after 35 years of HIV/AIDS, and would healing through the ages.

34 – Catch a concert at the Civic Opera House

The country’s second-largest opera house, Civic Opera House , opened in 1929 and although it was extensively renovated in 1993, it still retains its original beauty. Limestone sculptures, gilt paint, and an opulent Art Deco lobby are still the heart of the building, where the traditional and the contemporary mix perfectly.

During the renovation, structural improvements and a state-of-the-art new sound system were added. Major operas like Madam Butterfly and La Boheme, as well as more modern options like Fiddler on the Roof now play here year-round.

35 – Let your imagination fly at the Briar Street Theatre’s Blue Man Show

Once a horse stable for the 19th-century Marshall Field department store, the space was abandoned and then used for several purposes until it reopened as the Briar Street Theater in 1985. With just 635 seats and an intimate elegant setup, this is a great space to truly appreciate a performance in the heart of Chicago.

While the theater still holds other performances (including full-length plays and musical shows) from time to time, it has mostly become known as the home of the performing Blue Man Group, where three characters painted in blue lead a multi-sensory experience combining music, theatrics, and visual effects.

• Blue Man Show tickets

How to get to Chicago?

A number of European airports (including Amsterdam, London, and Frankfurt) offer direct flights to Chicago’s O’Hare International Airport. From there, you can reach the heart of the city using airport shuttles and regional buses in about 40 minutes.

If you’re carrying a lot of luggage or arriving late and would rather go directly to your hotel, you have the option of using local taxi drivers, but be aware that extra fees might apply during busy hours or if you’re carrying lots of bags.

To save time and hassle, you can book an airport transfer . You won’t have to worry about timetables and you’ll arrive directly at your hotel’s door quickly and efficiently so you can make the most of your time in the city.

Where to stay in Downtown Chicago?

Sitting in a prime location overlooking the Chicago River, the Swissotel Chicago knows how to do luxury well. Expect sleek accommodations, a fitness center with panoramic views, and an award-winning restaurant. Plus, you’ll be within walking distance of all major Downtown Chicago attractions and steps away from Lake Michigan.

Just steps from Millennium Park, the Hampton Inn Majestic is a more affordable option with a great location in the theater district. It offers colorful, spacious rooms, and a 24/7 fitness center, and it’s surrounded by great restaurants and cafes.

Right on the Magnificent Mile, the 4-star Millennium Knickerbocker Chicago offers innovative design, well-appointed rooms, a ballroom with a gold-gilded domed ceiling, great farm-to-table cuisine, and a 1920s-inspired cocktail bar.

• best hotels in Downtown Chicago

Visiting Chicago on a budget?

If you’re traveling on a budget but still want to see as many tourist attractions in Chicago as possible, the Chicago CityPass or the Go Chicago Explorer Pass might be for you.

Both offer discounts of 48% or more on up to 7 attractions chosen from a long list of 25 available attractions that include Skydeck Chicago, Adler Planetarium, the 360 CHICAGO Observation Deck, and the American Writers Museum.

The passes often include extras such as skip-the-line access and unique features and attractions like four-hour bike rentals, a panoramic night tour bus, and a shoreline architecture river cruise to choose from.

Some of the passes are valid for 60 days after activation, so if you’re visiting Chicago for a week you could easily do one attraction per day and save lots of money.

Final thoughts

We hope you’ve enjoyed our list of the best things to do in Downtown Chicago! With plenty of world-renowned cultural attractions, beautiful waterfronts with innovative architecture, and a past right out of a gangster movie, you won’t run out of exciting attractions here.

Have another favorite must-see attraction in Downtown Chicago to recommend? Let us know in the comments below.

Home » Travel Guides » United States » Illinois (IL) » 15 Best Things to Do in Downtown Chicago

15 Best Things to Do in Downtown Chicago

When you’re visiting Chicago, head for the downtown district and you’ll be in The Loop. It’s more than an urban spread of cloud-high skyscrapers and cultural recreation centers. You’ll be amazed by what you find.

The Loop is a community area of the city which covers over one and a half square miles, is fronted by the stunning shoreline of Lake Michigan and backed by the Chicago River. There are lakeside trails, riverside walks, and enormous parks as well as museums, art galleries, and historical monuments.

While you may be in the city, you can be forgiven for thinking you’re in a coastal resort as there are several beaches within a few minutes of the Loop too. Downtown Chicago really is a suburb of the city which has it all and more. Don’t miss out on any of these fifteen fantastic things to do while you’re there. You’ll be kicking yourself if you do.

1. Boat Cruise

By day or night one of the best ways to take in the Loop skyline is from on the water. Board a boat at the Navy Pier and be prepared to be impressed by sights of Downtown Chicago as you sail by. Whether you take a cruise down the Chicago River or on Lake Michigan, you’ll get stunning and unforgettable panoramic views of iconic buildings and the Loop’s prominent monuments.

There are lunch, brunch or dinner cruises. Cruises for sightseeing or ones which offer educational information on the city’s architecture. For adrenaline junkies, there are speedboat tours and extreme thrill rides which will get your heart pumping as you speed over the water at 45 mph.

For the romantics, watch the fireworks display on Navy Pier light up the night sky from a cruise boat. Combine that with dinner onboard and a spot of dancing for a perfect night out Loop-style.

2. The Picasso

Catch an eyeful of The Picasso. An arresting, unnamed sculpture which dominates the Loop’s Daley Plaza. The weighty steel sculpture stands around fifty-foot tall, and is the subject of an ongoing, fifty-year long debate as to what it actually represents.

Is it a winged horse, a dog or a Cubist representation of a preferred model? Your guess will be as good as anyone else’s. The Picasso, or the Chicago Picasso, which was a gift to the city from the famous French artist, makes an unusual and outstanding presence in the plaza. The sculpture has also been a background prop in several well-known movies and as strange a visage as it has, it’s surprisingly photogenic.

The sculpture makes an interesting centerpiece in the plaza during the festive or farmer’s markets and music events which are held there regularly.

Related tour : Chicago’s Modern Skyscrapers Guided Walking Tour

3. Pizza, Popcorn & Pumpkin Pie,

There are three things you just have to try when you’re in Downtown Chicago. They’re all iconic foodstuffs which the city claims to have created or has adopted as its own.

Chicago-style pizza is double deep-dish high and when its cut, as thick as a slice of cake. Oozing with chunky tomato sauce, melted cheese and layer upon layer of whatever other ingredient takes your fancy, it’s been a staple comfort food of the city for over seventy years. Sink your teeth into a slice at Pizano’s on Madison Street or Giordano’s on Randolph Street.

Chicago-style popcorn is an unusual, but tasty combination of two different flavors of popcorn. Cheesy kernels are mixed with others which have been coated with caramel for a unique taste sensation which has not just Chicago, but the whole state of Illinois, addicted. No one knows for sure how it came about and no one’s too worried so long as they keep making it. You can get yourself a bucketful at Garrett’s on E Madison Street.

The official pie of the state of Illinois is pumpkin pie. Spiced with cinnamon and with a pastry crust base to keep all that pumpkin custard under control, it’s a filling sweet treat. Don’t miss out on grabbing a slice or two while you’re in the Loop.

4. Willis Tower Skydeck

The Willis Tower or the Sears Tower as it’s also known once held the number one position as the tallest building in the world. While it’s now been surpassed by several others, its observation deck is still the highest in the US at one thousand three hundred and fifty-three dizzying feet. There are incredible views of Chicago and Lake Madison through the deck’s windows.

If you’ve got the nerve, you can make the experience even more memorable. Step onto The Ledge, a glass-walled and glass-floored box which juts four feet out of the building – one hundred and three floors above the ground.

If you’re on the Ledge and feel as if you’re developing vertigo, don’t worry. It’ll just the building swaying in the wind.

Book online : Chicago Skydeck Experience Ticket

5. Lakefront Trail

The Lakeside Trail is a nineteen mile long, asphalt and concrete pathway which runs adjacent to Lake Michigan shoreline from the South Shore Cultural Center in Chicago to the city’s Kathy Osterman Beach. Part of the trail runs through the Loop, and it’s the ideal place to get some fresh air and exercise.

Renting a bicycle or a pair of inline skates is a fun thing to do if you don’t want to walk or jog. You can access the trail from Grant Park or E Monroe Street as well as various other points throughout the Loop.

Riding or walking out to the Adler Planetarium is recommended. You’ll get some great views of the Loop skyline from there.

6. Historic Route 66 Sign

Head to East Adams Street, just off South Michigan Avenue in Downtown Chicago and look up. You’ll find a surprising historic monument there which will make a great photo for your Instagram account. Snap a shot with the historic Route 66 sign to get your own personal memento of the iconic highway.

Route 66 is probably the most well-known highway in the world and has been immortalized in films, songs and stories. The original road was almost four thousand miles long and stretched from Chicago right the way across the US to Santa Monica in California. It begins, and ends, in the Loop.

7. Grant Park

Grant Park is the Loop’s three-hundred and nineteen-acre green space which is bordered by Lake Michigan. Its wide boulevards are perfect for strolling; there are numerous flower gardens, fountains, monuments, and a three-acre skate park.

Inside its boundaries, Grant Park encompasses three other parks, the Millennium, the Maggie Daley and the Hutchinson Field, which offer visitors access to sporting facilities and artwork. Two marinas, a university campus and the Art Institute of Chicago. It’s also where the Petrillo Music Shell, the Cloud Gate and the Buckingham Fountain are. All of those, you can read about further on.

The park hosts amazing food and music festivals throughout the year. Time your visit to coincide with The Taste Chicago, Lollapalooza or the Chicago Blues Festival and you’ll see the park thronged with crowds.

Don’t miss out on seeing the Agora, a weird and wonderful sculpture comprised of over a hundred headless and armless figures. It’s definitely photo-worthy.

8. Buddy Guy’s Legends

When you’re in Downtown Chicago, there’s one thing you have to do, and that’s listen to some Blues. In the Loop, one of the best clubs to do that is Buddy Guy’s Legends.

The club is owned by Blues legend Buddy Guy, winner of seven Grammy awards plus a whole lot more and has influenced more musicians than he’s had hot dinners. Now at the age of eighty-one, he’s not on the stage every night, but other top Blues musicians are.

There are live shows nightly and an in-house restaurant which serves Louisiana soul food in honor of Buddy’s ancestral roots.

9. Cloud Gate

The Cloud Gate is one public sculpture you can’t walk past without noticing. The one hundred ton, shiny stainless steel “bean” which was inspired by a droplet of mercury, is eye-boggling.

The Cloud Gate is in the AT&T Plaza in Millennium Park. Walk underneath the Gate’s arch and look up to see a distorted version of yourself and those around you. It’s an unusual experience.

Stand at a distance from the Cloud Gate to capture a photo of the Loop’s twisted skyscrapers reflected on the sculpture’s curved surface. Amazing.

10. Loop Retail Historic District

The Loop Retail Historic District is much more than departments stores. This area of the Loop which covers over twenty-six acres is full of historic buildings and landmarks which are just as interesting from the outside as they are on the inside.

If you feel the need to shop, step into Macy’s on State Street. The store covers a full eight floors of retail space and ranks as the second largest store in the world. Clock the two seven-ton timepieces attached to the corners of the building before you go in because once you’re inside, you’ll forget about time completely.

11. Riverside Walk

Wander down the Loop’s Riverside Walk, and you’ll find more than a towpath running alongside the water.

The mile and a quarter long paved pathway is lined with beer gardens, restaurants with terraces and cafes. More than just a walk by the riverside, the Riverside Walk is one of the best social hubs in Downtown Chicago.

Don’t miss out on trying a traditional and handmade Italian ice cream from the old-fashioned handcart. Their flavors are to sigh for.

12. The Art Institute Of Chicago

The Art Institute of Chicago, on South Michigan Avenue in Grants Park, may be housed in what looks like a forbidding mausoleum, but inside it’s an absolute trove of treasures.

It takes a full day to browse around as there is so much to see. The museum has over three-hundred thousand permanent exhibitions plus hosts countless temporary exhibits throughout the year.

The artworks are not restricted to American artists. There are numerous and varied collections displaying the works of notable artists from all over the world in multiple forms which range from oils and watercolors to photographs, prints, textiles, and furniture.

Book online : Art Institute of Chicago Skip-the-Line Ticket

13. Buckingham Fountain

The Clarence Buckingham Memorial Fountain, to give it its full title, is not only the centerpiece of Grants Park and the symbolic feature of the city of Chicago, it is one of the largest fountains in the world.

The magnificent fountain is tiered in layer upon layer of pink marble, surrounded by eight seahorses and has a central jet which spurts water to a phenomenal height of one-hundred and fifty feet.

Catch the hourly water shows from the middle of April through to mid-October or the evening performances when the sprays dance in rhythm with lights and music. Impressive.

14. Petrillo Music Shell

If there’s an outdoor music festival happening in the Loop, it’ll be happening at the Petrillo Music Shell in Grants Park.

The Shell houses a massive stage plus all the high-tech sound and lighting equipment needed to satisfy even the most discerning of performers and audiences. It’s fronted by tiered seating for five thousand and enough lawn space to accommodate thirty thousand spectators more.

Whether you watch the live bands performing at the Taste of Chicago or attend the Chicago Blues Festival there, guaranteed, the atmosphere will be buzzing.

15. Miller’s Pub

Eat, drink and maybe spot a celebrity at one of the Loop’s oldest establishments. Miller’s Pub, on S Wabash Street, has been operating since 1935 and has been in the ownership of its current proprietors since 1950.

Check out the gallery of famous faces on the picture wall, then sit back in one of the booths and enjoy a rack of Miller’s infamous ribs or their trademarked, HenryJ corned beef hash followed by a slice of Key Lime Pie.

Miller’s is a Loop tradition, don’t miss out on dining there.

15 Best Things to Do in Downtown Chicago:

• Boat Cruise
• The Picasso
• Pizza, Popcorn & Pumpkin Pie,
• Willis Tower Skydeck
• Lakefront Trail
• Historic Route 66 Sign
• Buddy Guy's Legends
• Loop Retail Historic District
• Riverside Walk
• The Art Institute Of Chicago
• Buckingham Fountain
• Petrillo Music Shell
• Miller's Pub

The Ultimate Guide To Downtown Chicago

Chicago, home to a diverse array of cityscapes & cultures!

Chicago, a quintessential city with a multitude of skyscrapers, museums, beaches, waterfronts, nightlife, sports venues, shows, and performances, offers a blend of stunning cityscapes and several cultures!

Renowned the world over for its amazing architecture and some of the tallest structures in the world, Chicago needs no introduction! Considered the birthplace of modern architecture, Chicago’s architecture and skyscrapers have inspired several other high-rise structures in other parts of the world! However, it’s not just the towering steel and concrete structures but also the well-planned parks, museums, waterfront, and shopping districts throughout the town that make Chicago one of the most sought-after destinations in the US!

Once home to the Native Americans, Chicago has seen some significant and fast-paced development, despite the devastating  Great Chicago Fire  that caused a lot of damage to the city in 1871. However, nothing could stop Chicago from growing, and soon several industries, including transportation, manufacturing, advertisement, and commerce, flourished in the city and attracted several immigrants from all over the globe. Making Chicago one of the most culturally diverse cities in the US! 

Located in northeast Illinois, on the shores of Lake Michigan, Chicago is also popularly known as the Windy City due to the year-round lake breeze coming off Lake Michigan. Lake Michigan also gives Chicago its waterfront and beaches, and the Chicago River, flowing through the city amid the towering building, gives Chicago its unique canal system and water taxis. However, Lake Michigan is also responsible for the harsh winters and snowfall in Chicago, making Chicago a less desirable destination during the winter months.

Chicago has endless sightseeing opportunities, complemented with a few excellent land and river tours offered by a few tour companies!

Chicago is one of the most popular tourist destinations in the world, featuring several architectural wonders, world-renowned museums, a state-of-the-art planetarium, waterfront recreational activities, diverse neighborhoods, live performances, shopping districts, and some of the best culinary experiences. However, there’re a few great tour options, including narrated bus and boat tours, that make it pretty easy to navigate the city and explore the several attractions in Chicago.

Here is my ultimate guide to Downtown Chicago, featuring essential trip-planning information, significant attractions, Chicago attractions map, shows, tours, and recommendations on hotels and restaurants in Chicago!

Planning Your Trip To Chicago

Directly flying into Chicago international airport and staying in downtown Chicago is the best way to explore the city!

Best Time To Visit Chicago : Summer is the busiest season in Chicago, with warm temperatures ideal for waterfront and outdoor recreational activities. However, summer’s also the time when you’re most likely to stand in long queues to get inside a museum or an attraction. If you don’t mind slightly cooler weather, visiting in spring and fall is a great option to beat the crowd in Chicago. Winter is harsh with regular snowfalls and is not the best time for outdoor activities, but there’s a ton of indoor things to do in Chicago that can be enjoyed during the winter months too. 

Time Required At   Chicago : With so much to see and do in Chicago, I recommend spending a minimum of two days to see the city’s major highlights. However, if you have more time, you could spend an entire week exploring every museum, multiple neighborhoods, take various tours, enjoy some of the great shows, and of course, indulge in some of the best cuisines and restaurants in Chicago. 

Getting To Chicago : The best and most comfortable way to get to Chicago is by flying into Chicago O’Hare International Airport, located very close to downtown Chicago. Alternatively, you could also take a train or a bus to Chicago.

• Flight : Chicago O’Hare International Airport is the closest airport to downtown Chicago and is serviced by several airlines. Located about 20 miles from the downtown, O’Hare International Airport (ORD), Chicago, Illinois, is the best airport to get to Chicago. 
• Train : Chicago Union Station, located in downtown Chicago, connects several cities and states to Chicago and is also a major hub for several train networks in the US.
• Bus : Greyhound offers bus services to Chicago, with the closest Greyhound bus stop located in Harrison Street, right next to downtown Chicago.

Parking & Transportation In Chicago : Most hotels and attractions in Chicago offer paid parking, and there are quite a few public parking lots in the downtown area. However, if you’re flying into Chicago and staying in the downtown area, which I highly recommend, you really don’t need to rent a car in Chicago. Traffic and finding parking can be challenging in Chicago, especially during the summer months, the busiest season in Chicago. Additionally, most of the attractions in Chicago are located close to each other and are better explored using public transportation, private cab, or a guided bus tour that takes you to all attractions.

Tours & Multi-Attraction Passes In Chicago : I highly recommend using a hop-on-hop-off tour service in Chicago so that you spend less time driving and finding parking and instead have more time at your destination. The best way to explore Chicago is by using the  Big Bus Tours  and purchasing a multi-attraction discounted pass from  CityPASS  or  Go City . You don’t have to buy separate tickets for the Big Bus Tours as it’s one of the attractions included in the Go City pass. A trip to Chicago is incomplete without doing the  Chicago Architecture Boat Tour , a narrated river cruise highlighting several architectural landmarks of the city.

Lodging & Dining In Chicago : Chicago is bustling with hotels ranging from boutique hotels to bread and breakfasts! Though there’re several places to stay outside the downtown area, I highly recommend staying in Chicago downtown for easy access to the attractions and an authentic Chicago experience. The dining options in Chicago can be overwhelming, ranging from fine dining to casual waterfront dining, but you must try a few popular Chicago dishes, including deep-dish pizza, Chicago hot dogs, and barbecue when visiting the town. I have reviewed the lodging and dining options in Chicago in detail in the later section of this post.

Other Attractions Near Chicago : Unquestionably, downtown Chicago is the main tourist attraction in the state of Illinois and should be on top of your list. However, if you’re done visiting all Chicago attractions and still have time or would like to take a break from the hustle-bustle of the city, I recommend visiting the  Bahai House of Worship , located about 18 miles north of downtown Chicago, and  Anderson Japanese Garden , located around 85 miles northeast of Chicago. 

Things To Do In Chicago

Chicago Attractions Map

Chicago brief overview.

• Chicago Bus & Boat Tours
• Several Downtown Attractions
• Several Shows & Performances
• Several Lodging & Dining Options

Bus & Boat Tours In Chicago

The best way to explore Chicago is by using a hop-on-hop-off bus tour to get to the museums and landmarks and marveling at the grandeur of skyscraping structures on-board a boat tour! 

Given the several sightseeing options, including numerous museums, parks, architectural landmarks, and waterfronts spread all over the town, driving and finding parking can be very time-consuming and can be a big challenge, especially if you’re traveling during the summer months. So, I highly recommend using one of the tour companies that offer hop-on-hop-off bus tours and river tours to get the most out of your trip to Chicago.

Hop-on-hop-off Bus Tours : The hop-on-hop-off narrated bus tours in Chicago are a great option to learn about the city’s history and culture and easily get around the city. There are a couple of tour companies that offer hop-on-hop-off bus tours in Chicago –  Big Bus Tours  and  City Sightseeing . These companies provide quite frequent busses, and I love that Big Bus also offers a phone app using which you could track the real-time location of the next shuttle. 

River Cruises & Tours : There are several river & lake cruises offered in Chicago, starting from the Navy Pier and the River Walk area. The most popular being the Chicago Architecture Cruise offered by –  Shoreline Sightseeing Cruises  and  Cruise Chicago , departing from Navy Pier and River Walk. You could also enjoy Lake Michigan and Chicago’s skyline on-board one of the  dining cruises  offered at the Navy Pier. 

Multi-Attraction Passes : Buying a discounted multi-attraction pass from CityPASS  or  Go City  can really save you money and, most importantly time, that you would otherwise spend standing in queue to purchase tickets at each attraction. 

Chicago Downtown Attractions

Chicago Riverwalk

Chicago Riverwalk is a pedestrian-friendly walking trail along the Chicago River, starting at Lake Street and going all the way to the lakefront. The Riverwalk features spectacular views of Chicago’s skyline, several restaurants, boat rentals, and Architecture River Cruises and can be accessed from different junctions and districts in the town.

Willis Tower

Willis Tower, a 110-story skyscraper in Chicago, was built in 1973 and remained the World’s tallest building for 25 years. Currently, it’s the third-tallest building in the US and the 23rd-tallest building in the World. The Skydeck observation deck at Willis Tower offers stunning views of Lake Michigan and downtown Chicago.

Millennium Park

Located in the heart of downtown Chicago, Millennium Park is home to Chicago’s most iconic landmark, “The Bean,”   a reflective steel sculpture where you can see the city’s skyline along with your reflection. The park also features the Crown Fountain, Jay Pritzker Pavilion, and Maggie Daley Park.

Art Institute of Chicago

The Art Institute of Chicago, located adjacent to Millennium Park, is one of the oldest art museums in the US and is home to several artworks from all around the globe, including European armors, miniature rooms, pieces of furniture, and a lot more.

Adler Planetarium

Adler Planetarium, located in the Museum Campus along Lake Michigan, features several exhibits, galleries, and shows. Our Solar System, The Universe, and Mission Moon are some popular exhibits. The planetarium’s state-of-the-art dome theater offers several shows, including Planet Nine, Imagine the Moon, One World, One Sky, and Skywatch Live.

Shedd Aquarium

Shedd Aquarium, also located in the Museum Campus, is a large indoor aquarium that’s home to several marine creatures from all around the globe. However, being very popular among kids and having limited capacity, you may find long waiting queues at Shedd Aquarium.

Field Museum

The Field Museum of Natural History is a colossal museum featuring several sections that might take an entire day to explore. The Museum’s most popular exhibits include – Sue the T. Rex, the largest and most complete T. Rex ever discovered, taxidermy of the man-eating lions of Tsavo, and ancient Egyptian mummies.

Located on Lake Michigan, Navy Pier is one of the most happening places in Chicago. There’s a ton of things to do in Navy Pier – Navy Pier Centennial Wheel & Rides, Architecture River Cruise, Dining Cruises, Chicago Children’s Museum, Chicago Shakespeare Theater, Crystal Gardens, restaurants, and more.

Often referred to as Chicago’s front yard, Grant Park is a public park located in the Chicago’s Loop district. The Park’s most famous attraction is the Buckingham Fountain, one of the largest fountains in the world, runs from 8 AM to 11 PM, from mid-May through October. When operational, the fountain produces spectacular water and light displays for 20 minutes every hour.

360 Chicago

360 Chicago, an observation deck located on the 94th floor of another Chicago skyscraper at 875 North Michigan Avenue, is one of the best places to explore Chicago’s skyline. The experience is quite similar to Willis Tower, but 360 Chicago also offers a thrilling experience, Tilt, where you’re tilted on a glass platform extending from the building.

Museum of Science & Industry

Museum of Science & Industry

The Museum of Science and Industry, located on Lake Shore Drive, is a science museum featuring several exhibits displaying the technical, scientific, and industrial achievements of modern times. With several exciting displays, including a real Submarine, Science Storms, Fairy Castle, Mirror Maze, it might take an entire day to explore the Museum.

Shows & Performances In Chicago

End a hectic sightseeing day by watching a spellbinding show at one of many theaters in Chicago!

Chicago is home to numerous theaters featuring several entertaining shows, including concerts, live performances, stand-up comedies, musicals, and much more. Whether you want to see a Broadway show or a locally inspired play, you will find it in one of Chicago’s 250 theaters! Touring the downtown and marveling at the architecture in the daytime followed by dinner and a show is my idea about an ideal trip to Chicago! 

There are about 250 theaters in Chicago that host shows and live performances by several renowned artists, bands, and production companies. The theaters in Chicago can be grouped into three major theater districts – Loop, Edgewater, and Belmont. Below, I have listed the most famous theaters in each district, along with the popular shows and links to the websites, where you can book your show tickets.

The Loop : The most popular theater district of Chicago, the Loop is home to some of the best and elegantly decorated theaters in the US, including  Oriental Theatre ,  Cadillac Palace Theatre ,  CIBC Theatre ,  Auditorium Theatre ,  The Lyric Opera ,  The Goodman , and  Broadway Playhouse . These theaters host some of the biggest shows, including Wicked, Hamilton, A Christmas Carol, Jesus Christ Superstar, and more. 

Edgewater : The  Edgewater theater district  is a lakefront neighborhood that’s home to several independently owned stores and theaters hosting shows and performances of several theater companies, including   The Neo-Futurists ,  Babes with Blades Theatre Company ,  Jackalope Theatre Company , and  Raven Theatre .

Belmont : The  Belmont theater district  of Chicago, a large lakefront theater district, is home to several theaters that host stand-up performances and shows, including Blue Man Group, Bluebird Arts, Laugh Factory, The Newport Theatre, and others.

Lodging & Dining In Chicago

I highly recommend staying in downtown Chicago for easy access to the attractions and an authentic Chicago experience!

Hotels In Chicago : Staying in downtown Chicago has several upsides, including easy access to several attractions and tours, there’s no need to rent a car, and the liberty to enjoy late-night shows and nightlife. There’re several hotels in downtown Chicago, ranging from boutique hotels to bread and breakfasts. Here’re are my top picks for hotels in downtown Chicago

• Waldorf Astoria Chicago : Located in the heart of downtown Chicago,  Waldorf Astoria Chicago  is a luxury hotel featuring lavish guest rooms, spa services, and several dining options.
• Four Seasons Hotel Chicago : With easy access to Chicago’s shopping and theater districts, the luxurious  Four Seasons Hotel Chicago  is an excellent lodging option in downtown Chicago.
• Hyatt Centric Chicago Magnificent Mile : The  Hyatt Centric Chicago , located on the Magnificent Mile, offers contemporary rooms, excellent guest service, and a couple of on-site dining options.
• Chicago Marriott Downtown Magnificent Mile : Located on Michigan Avenue, close to the Magnificent Mile,  Chicago Marriott Downtown  offers modern amenities, great views, and culinary experiences.

Restaurants In Chicago : The dining options in Chicago can be overwhelming, ranging from fine dining to casual waterfront dining; you will find every cuisine in Chicago! There’re so many eateries in every street of the town it’s impossible to try them all and pick one over the other. However, here’re a few dishes and joints you must try when in Chicago – Giordano’s deep-dish pizza, Chicago hot dogs, and Chicago’s famous barbecue ribs, sandwiches and shakes at Portillo’s, and mouthwatering Eli’s Cheesecake.

Other Illinois Attractions & Related Posts

Baháí House Of Worship

Anderson Japanese Gardens

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Cruises & Tours

Explore chicago by land, water or air.

Whether you’re in town for just one day or are a life-long resident, cruises and tours of Chicago are a great way to see the sights, discover something new, or treat yourself to an unforgettable experience.

From laid-back sightseeing cruises and elegant dining cruises to heart-pumping thrill rides to upscale private charters, Lake Michigan and Chicago River cruises departing from Navy Pier offer a memorable experience for all.

Our Cruises & Tours

Architecture & Sightseeing Cruises

Take in Chicago’s iconic skyline and the scenic Chicago River with sightseeing cruises at Navy Pier! These fun experiences offer guests panoramic city views along with entertaining and enlightening commentary about Chicago’s architecture and history.

Brunch, Lunch and Dinner Cruises

When you dine on Like Michigan, every table is the best in the house. Navy Pier’s brunch, lunch and dinner cruises pair world-class cuisine with panoramic views of the city and lakefront.

Speedboat Tours and Thrill Rides

This isn’t your parents’ leisure cruise! On these 30-minute speed boat rides, you’ll tear across Lake Michigan at up to 45 miles per hour while getting entertaining and informative commentary on Chicago.

Specialty and Holiday Cruises

There’s always something worth celebrating with cruises on Lake Michigan and the Chicago River. Our partners offer themed cruises for major holidays, as well as a wide variety of special events that are sure to get you in the party mood.

Groups And Private Charters

Perfect for corporate outings and special occasions, group cruises and private charters offer unforgettable experiences for up to 800 guests.

Bicycle Tours

Bike & Roll Chicago allows guests to rent bicycles for a fun experience on the lakefront.

Our Cruise Partners

Discover our partners: Spirit Of Chicago, Shoreline Sightseeing, Seadog Cruises, Odyssey Lake Michigan, Mystic Blue, Chicago Elite Private Yacht, & Tall Ship Windy

Cruise & Tour Types

Shoreline Architecture River Tours

Take Shoreline’s award-winning 75-minute Architecture River Tour to discover Chicago’s renowned landmarks as presented by our expert and entertaining guides. You’ll learn how Chicago rose...

City Cruises – Premier Dinner Cruise on Lake Michigan

Lake Michigan dinner cruises are the perfect setting for celebrating with friends, connecting with colleagues, or a romantic evening. Odyssey Lake Michigan dinner cruises are...

City Cruises – Premier Lunch Cruise on Lake Michigan

A two-hour Lake Michigan lunch cruise is the perfect way to enjoy time with family or the company of great friends. Retreat from a busy...

City Cruises – Signature Dinner Cruise on Lake Michigan

Celebrate a special occasion, host a group event or share a romantic evening aboard Spirit of Chicago. Great for parties of all sizes, a Spirit...

City Cruises – Spirit of Chicago Dinner Cruise

Catch the Chicago skyline at sunset during the most beautiful time of the year, and join us for a fun, laid-back, 2-hour cruise. Spirit's Lakefront...

City Cruises – Odyssey Lake Michigan Dinner Cruises

Odyssey Lake Michigan presents special prix fixe dinner cruises, offering guests the opportunity to try one of Chicago’s most unique dining experiences at an incredible...

City Cruises – Spirit of Chicago Brunch Cruises

Whether you’re a native Chicagoan, newcomer, or just visiting, a Spirit of Chicago brunch cruise is the perfect weekend outing. See well-known Chicago attractions from...

City Cruises – Signature Lunch Cruise on Lake Michigan

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DOWNTOWN CHICAGO TV & MOVIE SITES TOUR

Quick Details

• Calendar Availability: Daily
• User Ages: All ages
• Hour Glass Duration: 2 hours
• Tag Tour Type: Walking Tour/Self-Guided Tour
• Open Book Language: English

Downtown Chicago TV & Movie Sites Tour by On Location Tours

Enjoy a two-hour walking trip down movie-making memory lane as you visit sites from shows and movies like Ferris Bueller’s Day Off, The Untouchables, The Dark Knight, The Bear, and many more.

The tour begins near the Roosevelt University Auditorium Building, and features several iconic landmarks featured on-screen, including the Willis Tower, The Art Museum of Chicago, and Millennium Park. Kick off or wrap up your Chicago adventure with your family and friends as you see these city landmarks from a new blockbuster perspective. Throughout the tour, your tour guide, a local actor/actress, will offer interesting facts, trivia and behind-the-scenes scoops. See the sites where your favorite stars filmed your favorite tv shows and movies on the Downtown Chicago TV & Movie Sites Tour!

Looking for a more intimate way of seeing Chicago’s most-filmed locations? Check out our private tour options!

What Will You See On This Tour?

• Visit the Willis Tower and Calder’s Flamingo sculpture as you relive the parade scene as seen in Ferris Bueller’s Day Off
• Take a trip down to the L Train as seen in movies like The Fugitive, High Fidelity, and While You Were Sleeping
• Flash your group back to the early 20th century and live out your mobster lifestyle dreams at locations where Road to Perdition, The Untouchables , and Public Enemies were filmed
• Live out the iconic chase scenes featured in Blues Brothers
• Save Gotham with your favorite caped crusader as you visit Bruce Wayne’s penthouse building, the site of Harvey Dent’s fundraiser, and Harvey Dent’s office building, all seen in The Dark Knight

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Things to Do in Downtown Chicago

What to do in the loop.

This post will cover some of the most interesting things to do and see while visiting Chicago’s Loop neighborhood.

Since the Loop is a vibrant community of work and play, every traveler will find something that suits their tastes!

To write this post, I relied on the extensive experiences that I and my fellow local tour guides have of SoHo.

We lead dozens of  guided walking tours  through the streets of the Loop every week, guiding hundreds of visitors each week.

We know a thing or two about this place. We even wrote and published an audio tour of the area.

Listen to a sample of our Downtown Chicago Tour, written and recorded by one of our tour guides.

• What is the Loop
• 10 Things to See and Do
• Chicago City Pass Attractions

WHAT IS THE LOOP?

The name derives from the circle or “loop” that the cable cars in the 1800s made in this area and currently the elevated trains run along the same circular path.  

Alternatively, you can also get here using a hop-on-hop-off bus tour.  All bus companies have multiple stops in the Loop.

You can reach this area easily by using Chicago’s Public transit.  If you are new to Chicago, read our guide to using public transit .

And if you are driving in, a good parking lot is the 60 East Lake Street parking garage .

TOP THINGS TO SEE AND DO IN AND AROUND THE LOOP

There are a number of things to do in and around the Loop. Below are a few suggestions.

1. Explore the Architecture

While many visitors will stroll along the Riverwalk or take a boat tour to get their Chicago Architecture views, many of the architectural gems are hidden right in the Loop!  

One example of a great building that also has free events is the current Chicago Public Library and the past Chicago Public Library, now the Chicago Cultural Center. 

Both of the buildings are extraordinary and both have free programming!

To learn about the Chicago Cultural Center, join us on our seasonal Pedway Tour or Holiday Tour.

Hop onto our Birth of the Skyscraper-Architecture Tour to learn more about the current Chicago Public Library.

It also covers well-known Windy City landmarks in Grant Park such as the Willis Tower (formerly the Sears Tower) and visits Buckingham Fountain.

You'll also see some of the buildings on our Chicago Riverwalk and History Tour which talks about locations such as The Chicago Theater, The Wrigley Building, and The Chicago Tribune Building

The Magnificent Mile Tour takes guests past notable buildings such as The Tribune Tower, The John Hancock Building, and The Wrigley Building.

The best way to appreciate this living history of buildings is on our architecture tour but roaming on your own is still a perfect way to spend an afternoon.

If you want to try that you might like our Downtown Self-Guided Tour .

You might also enjoy the Chicago Architecture Center ( t h e CAC) which offers programs and presentations that display the architectural legacy of Chicago, as well as its ongoing innovations in this field.

2. Check out the Theatre District or Movies

The Loop was originally an area of old movie palaces, vaudeville acts, and jazz clubs.

Today it is a bit tamer, but still famous for a few iconic movie palaces turned into concert or theatre venues.

Theatres in the Loop area include:

• The Nederlander : a Broadway touring house
• The Chicago Theatre : holds concerts and special events
• The CIBC Theatre : a Broadway touring house
• The Goodman Theatre : the oldest regional theatre in Chicago
• Cadillac Palace Theatre : a Broadway touring house

If you are a film-lover, visit the Gene Siskel Film Center to catch film festivals, independent films, student films, foreign films, and art films. 

It is located at 164 N. State Street.  

If you’d like to catch the best big blockbuster, head to the AMC Movie Theatre at the Block 37 Mall. 

You can watch the next big hit while in a recliner and eating your dinner.

Pro-tip: Check out our self-guided Downtown Chicago Theatre Tour if you love theatre buildings .  

Of course, Chicago theatre is not limited to this one neighborhood and we encourage all visitors to travel outside of the Loop!  

To see a full calendar of all shows or to buy tickets for shows, click here .

3. Visit the Tallest Building in Chicago

The Willis Tower (known as the Sear Tower to locals) was the tallest building in the world from 1973-1998 standing at 442 meters (1.450 ft) with 110 floors.

While it isn’t the tallest in the world anymore, Chicago is still fiercely proud of the Skidmore, Owings, and Merrill Building! 

If you aren’t afraid of heights, check out the Willis Tower Skydeck which is on the 103rd floor at 1353 feet (412.2 meters).

You will see a spectacular view of the Chicago skyline and Lake Michigan.  

Our post on observation decks in the Chicago area will give you information on a few different places for a great view.

For a unique experience, step out onto the “Ledge”, an included attraction where you can stand directly over the street!  

4. Visit Millennium Park & Cloud Gate

While a bit outside of the official Loop, Millennium Park is still considered a part of the Loop neighborhood.

This park was built to celebrate the turn of the century and opened in 2005. 

Inside Millennium Park , there are many lovely gardens and several pieces of notable public art; the most recognizable is “Cloud Gate” which is more commonly referred to as “the Bean”.

This stainless steel reflective piece by Anish Kapoor is the centerpiece of Millennium Park. 

Learn more about it on our Loop & Millennium Park Tour.

Things to see in Millennium Park:

• Cloud Gate designed by Anish Kapoor
• Pritzker Pavilion designed by Frank Gehry
• Crown Fountain designed by Jaume Plensa
• Lurie Garden is a 5-acre garden that pays homage to our city motto “The City in the Garden”
• Wrigley Square and Millennium Monument (Peristyle) to honor the Millennium Park Founder’s
• The rotating Boeing Galleries - constantly changing public art
• BP Bridge designed by Frank Gehry (which heads to Maggie Daley Park)
• Nichols Bridgeway designed by Renzo Piano (which heads to the Art Institute’s Modern Wing)

Note that just across from Millennium Park is the famous Chicago bull statue, near the corner of N. Michigan Avenue and Washington St.

5. Enjoy Events at Pritzker Pavilion

During the summer months, the Pritzker Pavilion is an active hub of music, dance, and special events.

The best part is that all of the events are free!  

• Mondays & Thursdays: Enjoy concerts in the park with their summer music series.
• Tuesdays: You can watch movies in the park at their summer film series.  
• Tuesdays & Thursdays: There are early morning fitness classes with the summer workout series.

During the winter months, it is still a lovely destination because you can appreciate the incredibly artistic structure designed by the famed Frank Gehry himself.

6. Visit the Art Institute

The Art Institute of Chicago which was founded in 1879 is one of the oldest and largest art museums in the United States.

Travelers from all over the world visit peer onto Monet’s haystacks, Van Gogh’s self-portraits, and Seurat’s “Sunday in the Park.”  

Inside the Art Institute, you will find a unique Chicago treat, the Louis Sullivan original trading room from the original Board of Trade reassembled.

Also, behind the Art Institute is an original stock exchange arch design by Adler and Sullivan.

For information on ticket discounts, read our post: Art Institute Tickets and Discounts .

Pro Tip:  hop-on-hop-off bus tours stop right outside of the Art Institute!

Fun Fact:  The Art Institute is technically the location of the start of Route 66!  Be sure to find the Route 66 start sign!

7. Discover Public Art

The art in Chicago isn't always in museums - though Chicago has a great art museum centrally located near the Loop.

However, much of what you can find in the city is public art.

No entry fee, no docent - in fact, no walls. They are outside in parks and plazas!

Our post, Public Art in Chicago covers some of the works below in more detail.

• The Flamingo : designed by Alexander Calder can be found at 50 W. Adams St.
• Chicago’s Miro : designed by Miro is located across from Daley Plaza at 69 W. Washington St.
• Four Seasons: designed by Marc Chagall can be found at 10 S. Dearborn St.
• Monument with Standing Beast : designed by Jean Dubuffet is located at 100 W. Randolph St. in front of the Thompson Center
• Chicago’s Picasso: designed by Pablo Picasso, this sculpture is in Daley Plaza at 50 W. Washington St.
• Lions at the Art Institute: by Kemley are in front of the Art Institute at 111 S. Michigan Ave.
• Crown Fountain : designed by Jaume Plensa in Millennium Park at 201 E. Randolph St.
• Cloud Gate : by Anish Kapoor in Millennium Park at 201 E. Randolph St.

More recently, Chicago has started an exciting mural project in the Loop as well!

Check here for details about the Wabash Arts Corridor. 

More and more we are finding updated street art in the Loop, like the Muddy Waters mural memorializing the famed blues musician at 17 N. State St. by Kobra.

8. Stop In At Marshall Field’s

To visit a truly iconic Chicago establishment, you’ll need to visit the old Marshall Field building which is now the Macy’s on State Street.  

Architecturally, this building is a delight, but it is the inside that counts.

There is an incredible Tiffany Glass ceiling above cosmetics that will delight every traveler passing through.  

Looking for a perfect lunch destination? Head to the 7th Floor for the famous Walnut Room. 

This was the first restaurant opened in a department store.

After lunch, if you explore the 7th floor, you will see a wall of history about Marshall Fields.

The history of this building is quite interesting and is told on our Loop & Millennium Park tour.

If you have time to wander, go to the basement which boasts a tasty candy shop to sample Marshall Field’s Frango Mints. 

You’ll also find a very affordable cafeteria-style lunch destination in the basement if you find yourself needing a snack. 

When you are ready to leave, wander out through the Pedway through the stained glass museum.  

9. Visit the Museum Campus and Other Loop Museums

Museum Campus Chicago is a 57-acre green oasis on the lakefront situated at the south end of Grant Park.

The campus was first imagined back in 1909 and has grown since, bringing a number of art institutions closer together while also providing a shared area where folks can gather.

Today you'll find the Field Museum of Natural History, the Shedd Aquarium, and the Adler Planetarium, along with Solder Field, McCormick Place Bird Sanctuary, Northerly Island, and McCormick Lakeside Center.

For discounts and free days, read our posts on:

• The Field Museum
• The Shedd Aquarium
• The Adler Planetarium

The American Writers Museum is another Loop option for anyone who loves literature.

Head to the Money Museum if you are fascinated by old bills and the process of printing money.

The Museum of Contemporary Photography has an impressive range of collections and exhibitions from contemporary photographers as well as emerging and established artists.

With more than 30,000 photographs, including works by renowned names such as Diane Arbus, Walker Evans, and Robert Frank, the Museum of Contemporary Photography is nothing short of a treasure trove!

10. Relax in Daley Plaza

The Daley Plaza in Chicago is a great place to meet locals! 

It is a public square that is the home to the Picasso Statue which was a gift from Pablo Picasso. 

It is the perfect place to enjoy local coffee while pigeon watching or to catch a special event.  

• Thursdays, May - October are Farmer’s Market Days
• Saturdays, March - October are Food Truck Days
• Most weekends are daily lunch hours with House Music 
• Several times a week, there is a special event or concert
• Every day between late November-December 24- German-inspired Christmas Market

While you are in Daley Plaza, things to look for in the plaza or nearby include: 

• The Veteran’s Memorial - Next to the Picasso
• Miro’s Chicago statue across the street
• The First United Methodist Church - is across the street and is magnificent.  Check out their free “Chapel in the Sky” tour Tuesdays-Saturdays at 2 pm. 
• City Hall- An incredible building inside and out designed by Holabird and Roche
• The Daley Center built in 1965

Pro-Tip: Since the Loop is such a central area- there are often parades downtown- often marching right past Daley Plaza. Be sure to check out the parade schedule here.

11. Take in Some Shopping and Food

The Loop is known for the shopping along State Street and the tourist shops on Michigan Avenue. 

Michigan Ave. is arguably downtown Chicago's most famous street.

State Street is considered the shopping district of the Loop and is loaded with more discount shopping (unlike the Magnificent Mile with designer brands).  

You’ll find shops like Macy’s, H&M, Old Navy, Nordstrom Rack, and Urban Outfitters.

The largest mall in the area is Block 37 which has shops like the Disney Store, Zara, and a custom tennis shoe store.

As for food, the Loop has many delicious options for visitors who love to travel through food!

Of course, the most famous Chicago foods are: Pizza , Hotdogs, and Italian Beef Sandwiches, but Chicago is a food city and we pride ourselves on options! 

See below for just a sampling of food choices in the Loop area.

Iconic Chicago:

• Al’s Beef : 169 W Ontario St. | best known for their Chicago Hot Dog and Italian Beef Sandwich
• Italian Village : 71 W Monroe St | The oldest restaurant in the Loop
• Billy Goat Tavern : 60 E Lake St | While not the original location, still quite tasty!
• The Bergoff : 17 W Adams St | a German restaurant that received the first liquor license after Prohibition
• The Walnut Room : 111 N State St | a beautiful and historic restaurant on the 7th floor of Macy’s
• Pizano’s : 61 E Madison St | thin crust and deep dish pizza
• Giordano’s : 223 W Jackson Blvd | thin crust and deep dish pizza
• Garrett’s Popcorn : several locations! | Chicago’s official snack food

Budget Eats:

• James R. Thompson Center : 100 W Randolph | a giant American food court
• Taco Bell Cantina : 178 N Wabash | one of the first Taco Bell to serve alcohol
• Jason’s Deli : 195 N Dearborn | healthy choices and comfort foods
• Potbelly : several locations | a chain sandwich shop

Indulgent Meals:

• Petterino's : 150 N Dearborn | delicious Italian food with caricatures of the famous on the walls
• Rose Bud : 70 W Madison | a great date location with steak and pasta
• The Dearborn : 145 N Dearborn | chic American dining
• The Drawing Room / Chicago Athletic Association : 12 S Michigan Ave. | amazing view and amazing meals
• Catch 35 : 35 W Wacker | high-end seafood

Unique Places:

• Revival Food Hall : 125 S Clark | over 15 local eateries in one convenient and gorgeous location

12. Visit Navy Pier

Chicago's Navy Pier, lovingly called the "People's Pier," has certainly come a long way since it was originally constructed in 1914 as the world’s largest pier at 292 feet wide and 3000 feet long (89m x 914m). 

Navy Pier (originally called Municipal Pier #2) was built for shipping and entertainment.

Today, it is a cultural hub for locals and visitors of Chicago to explore unique dining, free and paid arts and entertainment attractions, and popular cultural exhibits

This is a great place to take kids as they're sure to enjoy the Centennial Wheel, a giant Farris wheel.

The Chicago Children's Museum is also there.

For more ideas of things to do, read our post 16 Top Things to Do at Navy Pier .

13. Enjoy Chicago Entertainment

Chicago is known for its comedy! Some of the best comedians came out of the Windy City; Bill Murray, Amy Pohler, Tina Fey, and Chris Farley, to name a few.  

During the chilly nights of March, a good laugh will be sure to warm you up. 

Check out Second City for sketch comedy, stand-up, and improv. 

Another local favorite is  i.O.  which is improv and sketch, and you can head to the  Laugh Factory  for stand-up.

You might visit the United Center for all sorts of events, from music to sports (the Bulls and Blackhawks play here).

Find tickets to United Center events here .

Stroll (run, bike) the Lakefront Trail.

This 18-mile trail runs along the western coast of Lake Michigan and is a favorite for walkers, runners, and those with bikes.

Best of all it's free. For more free things to do in Chicago, read our post .

The Lincoln Park Zoo is one of the oldest zoos in the country, and one of the last few free zoos.

With over 1,000 animals to see, kids are sure to enjoy it. Read our post Things to Do at the Lincoln Park Zoo .

14. Visit the Water Tower

As one of the oldest structures in Chicago's Loop area, the iconic Water Tower stands on North Michigan Avenue on the Magnificent Mile.

Originally built in 1869 to house a water pump that supplied nearby citizens with water, it was one of few buildings able to withstand the Great Chicago Fire of 1871.

Its significant role during this disaster - aiding firefighters in putting out raging flames - has made it a symbol of the city's strength and resilience.

The tower stands 154 feet tall with a square structure made entirely of limestone and features Gothic-style architectural elements.

It is listed on the National Register of Historic Places and has been used in a variety of ways, including as a public library branch and office for the renowned Chicago Park District.

Today there is an art gallery inside, City Gallery , which features photos of Chicago by photographers from the city.

CHICAGO DISCOUNT PASSES

While most of the things in the Loop aren’t on the Chicago City Pass- a few are! Many of Chicago’s biggest attractions have entry fees.

While you do pay for a tourist discount pass, it can give you a bulk discount and free admission into some interesting tours and museums, saving you up to 55%.

They can also save you time with skip-the-ticket-line privileges.

Each Chicago Tourist Discount Pass includes a variety of fun family-friendly activities and attractions.

Here are a few examples of what you can visit with a tourist pass, for a discount, or for free.

• Shedd Aquarium
• Skydeck Chicago
• Adler Planetarium
• Art Institute of Chicago
• Museum of Science and Industry   
• 360 Chicago Observation Deck

For more details, make sure to read our full post covering Chicago tourist passes .

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Chicago River Architecture Tour

Chicago's Original Architecture Tour®

Experience the city’s legendary architecture from the best seat in the house—the river. Our experienced tour guides detail the 130 year long history behind the skyline, while our bartenders and staff keep you comfortable and entertained. This comprehensive tour navigates through the heart of the city on all three branches of the Chicago River. It’s the one thing everyone tells you to do in Chicago, done right.

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• Adult: $44.00
• Child (4-12): $20.00
• Under 4: Free (ticket required)

TICKETS ARE NON REFUNDABLE BUT ARE TRANSFERABLE.

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