willis tower tour chicago

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The Height of Experience in Chicago

There’s something for everyone at Willis Tower. From grab-and-go dining options, to the thrilling views of the Skydeck, lush public greenspaces and everything in between.

Discover Catalog

Elevate your mood by visiting Willis Tower’s expansive, five-level retail and dining destination featuring a vibrant collection of merchants.

Step outside the third tallest building in the Western Hemisphere at 1,353 feet in the air, the Ledge’s glass boxes extend out 4.3 feet from the Skydeck. On your way up, check out the new 30-60 minute Chicago experience featuring the city's rich history.

Pictured above: Explore the City Like Never Before

Meet at Convene

Offering 70,000 square feet of meeting and event space in Chicago's iconic Willis Tower. Easily accessible for locals and out-of-towners.

Art of the Neighborhood

Stunning public installations by world-class artists — Immerse yourself in the local art scene with a trip featuring Olafur Eliasson and Jacob Hashimoto.

Elevated Spaces

TONE is a 30,000 square foot, state-of-the-art, tenant-exclusive fitness center

Tower House is a casual work and meeting place for tenants, complete with a café and bar.

Delivering the quintessential Chicago experience, the ideal space to inspire and impress.

A sophisticated tenant lounge and café with truly stratospheric views.

Offering 70,000 square feet of meeting and event space in Chicago's iconic Willis Tower.

Private club offering curated, aspirational and dynamic atmospheres on floors 66 and 67

The Terrace

Outdoor greensapce on top of Catalog, open to the public and all tenants.

Spectacular 360-degree views of Chicago, awe-inspiring space for special events.

Community Programming

Women of Willis is a building-wide networking initiative created to empower, elevate, and connect the women working within our neighborhood.

A new wide-ranging tenant-exclusive series of talks, panels, and workshops to spark creativity, foster collaboration, and drive success. Brought to you by EQ Office and Willis Tower.

Find Your Space

• Willis Tower App
• Tenant Resources
• Accessibility
• Health + Safety

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Skydeck Timed Tickets

Tickets are selected based on date and time. Select your date and then the time to gain admission into the line to access the elevators to reach the Skydeck, floor 103. Spaces are limited per 30 minute periods.

See amazing animals, incredible views, fascinating science, world-class art and more with Chicago CityPASS tickets.  One single purchase with 9 consecutive days of validity with line-skipping privileges at select attractions and instant delivery with convenient mobile or printable tickets.

Willis Tower Revitalized

Celebrate the 50th anniversary of Willis Tower with a trip to the 103rd-floor Skydeck combined with a tour of the transformative $500M redevelopment featuring a visit to Catalog’s restaurants and experiences and an exploration of the Tower’s history and construction.

Willis Tower, originally the Sears Tower, is one of the first super-tall skyscrapers. See how the Tower has been re-imagined for the 21st century. Guests will learn about the Tower’s history including its design and construction and experience the recent redevelopment to the exterior and interior s  that have revitalized the Tower and brought it to the forefront of sustainable skyscrapers. The guided tour portion visits the public spaces of the Tower, including its hospitable lobbies and 300,000 SF retail, dining and entertainment destination known as Catalog. A visit to the Skydeck and the glass Ledge at guests’ own pace is included in the ticket price.

About Skydeck Chicago

Skydeck Chicago is the breathtaking, thrilling observatory atop the iconic Willis Tower. The highest observation deck in the United States, Skydeck provides views of the city spanning up to four states and 50 miles on a clear day. Skydeck features The Ledge; five glass floor balconies extending 4.3 feet from Willis Tower and made up of three layers of half-inch thick glass laminated into one seamless unit. After an extensive transformation, Skydeck offers a can’t miss, one-stop attraction to discover and see all that the city of Chicago offers from an incomparable vantage point. The revamped attraction features a brand-new, lower-level, museum-like interactive experience that celebrates the unique personality, history, neighborhoods, and sites of Chicago.

Notes: 

• This tour requires advance reservations. Ticket sales close at 4 p.m. the day prior.
• Ticket Price includes a visit to the 103rd-floor Skydeck and Glass Ledge at the conclusion of the tour.
• Ticket Price includes entrance to the Chicago Architecture Center within 7 days of your tour. View the CAC's hours .
• Refunds and exchanges are not permitted with less than 24 hours notice

Upcoming Willis Tower Revitalized Tours

Thursday apr 18.

• 9:30am Buy Tickets

Thursday May 2

Thursday may 16, thursday may 30, thursday jun 6, thursday jun 13.

©Veni/Getty Images

Willis Tower

Top choice in Chicago

Willis Tower is Chicago's tallest building (and one of the world's loftiest). Breathe deeply during the ear-popping, 70-second elevator ride to the 103rd-floor Skydeck , then stride to one of the glass-enclosed ledges that jut out in midair for a knee-buckling perspective straight down some 1400ft.

A bit of history: it was the Sears Tower from its completion in 1973 until insurance broker Willis Group Holdings bought the naming rights in 2009. The building held the title of world's tallest building for almost a quarter century, surpassed by NYC's One World Trade Center in 2013.

Tickets and other information

Tickets are timed and should be purchased online in advance of your visit. The Skydeck is fully wheelchair-accessible, with complimentary wheelchairs available on a first-come, first-served basis. There are specific facilities for family travelers too, with quizzes and games for children. 

The entrance is on Jackson Blvd. Even with pre-booking, lines can take up to an hour on busy days (peak times are in summer, between 11am and 4pm Friday through Sunday, although some say sunset is the best time to visit).

233 S Wacker Dr

Get In Touch

312-875-9696

https://www.theskydeck.com

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Looping The Loop: spring fever hits the Windy City before a busy summer

It’s been 40 minutes now. 

Forty minutes of looping around The Loop trying to find the entrance to the Fairmont Chicago, Millennium Park in order to check in — after a nine-hour drive at that. Nerves became a little frayed under such conditions and The Loop, the fitting nickname for Downtown Chicago, is trying patience, worse than I90’s lengthy tests.

The GPS keeps returning the car to this dark underground roadway, from which we keep emerging. Round and round, again and again — the car has already driven along delightful Lake Shore Drive so many times it knows it’s own way there.

On this fifth loop around, the picturesque stretch has lost its charm. Then, as despair and exhaustion reach breaking point, instead of adding the hotel name, an address is tapped in instead — and bingo. Not a minute too soon we are finally pulling into the semicircular drive, welcomed by a very understanding valet. Live and learn — AI trains us, not just the other way round.

And so, deep breath, the poor automobile is off for a deserved rest. The human needs something similar, too — and that is soon happening. A beer and a bite in the hotel’s Columbus Tap — a sports bar type place with a surprisingly tasty Beyond burger, and lots of local beers to choose from — caps a long travel day nicely.

A busy city

This towering, multilayered, madcap city sat by the once mighty, much abused Lake Michigan, which stretches into the distance, creating a veritable third coast, awakens from its bitter winter’s lull with a fabled St. Patrick’s Day parade in March. But this coming summer sees Chicago in the spotlight as host the 2024 Democratic National Convention in August. Oh, and the NASCAR street race will rev through the city again that month; while the annual Lollapalooza takes over Grant Park for a weekend of music too. It is followed by Riot Fest in early September — yet another music jamboree.

The Loop reverberating to the sounds of the Red Hot Chili Peppers, one of Lollapalooza’s headliners last summer, was a sharp contrast to a springtime wander through soothing Grant Park. Late spring sunshine in full glow, a different sound of music emanated from the stage at the eye catching Frank Gehry designed Jay Pritzker Pavilion , which is home to the annual 10-week classical Grant Park Music Festival , featuring the Grant Park Symphony Orchestra and Grant Park Chorus, along with guest performers and conductors. This was a lunchtime orchestral rehearsal and anyone was free to sit and listen; what a treat. The Grant Park Music Festival runs mid-June through mid-August, usually; and concerts are free, too (201 E. Randolph St. grantparkmusicfestival.com ).

This early spring sees Expo Chicago, the International Exposition of Contemporary & Modern Art , now part of the London-based Frieze, at the Navy Pier’s Festival Hall, Apr. 12-14 ( expochicago.com ).  Set by the lake, the Navy Pier includes a fun fair and other traditional attractions, as well as theaters. Some might call it a tourist trap. Before setting off the Navy Pier, still undecided, a chat with a woman and her young son exploring the beautiful Fourth Presbyterian Church of Chicago on Michigan Avenue was the decider. The woman said they live in the condos overlooking the lake near to the Navy Pier: Mom: “Only tourists go there.” Son, countering mom’s put-down with a more considered approach: “But it’s a lot of fun to visit sometimes.”

Quite the opposite to the pier’s colorful fun, one of the most beautiful places in Chicago is Millennium Park’s wildflower garden. There are no superlatives to describe the respite this place offers to all beings: spring buds and brave early blooms lead to summer’s untamed beauty of plant-life left to be, and become a place buzzing with red admirals, peacocks, and monarch butterflies fluttering amongst bee and fly laden flowers. 

But, it is likely Millennium Park’s shiny sculpture The Bean that is a bigger draw — it’s a selfie heaven for the camera clique, this beautiful artwork, reflecting and refracting, and oddly calming in that.

Skyscrapers and wildflowers 

Chicago is better known for its skyscrapers than its wildflowers — this is where up-up-upward mobility in building was birthed. Every city has a high tower experience now, but, among the oldest, the Skywalk at the Willis Tower just turned 50 and is still a landmark. Formerly known as the Sears Tower, this was once the tallest building in the world, but tallest kept getting taller and now it’s simply historic — and tall. Step out onto its new glass floor, if you dare.

Chicago recently added another supertall: The St. Regis Chicago , a sleek, spindly 101-story skyscraper, designed by award-winning architect Jeanne Gang. This is now the third tallest building in Chicago, the 10th tallest in the United States, and the tallest building in the world designed by a woman. 

Back deeper in The Loop, the Langham Chicago is set in a 52-story landmark tower, built in 1971 as IBM's regional headquarters, and the last project designed by renowned architect Ludwig Mies van der Rohe, the father of Chicago’s modernist skyline.  Or is that post-modernist? With a touch of brutalism?

Around the city

One of the most interesting ways to find out which it is, and about The Loop’s mass of buildings is to take the First Lady Architecture River Cruise Tour, which not only navigates the Chicago River — the only river in America that flows backwards, but, in partnership with the Chicago Architecture Center, the cruise guide gives the backstory to the structures that already pack The Loop, and what’s to come.  The dock is located on Chicago's Riverwalk at Michigan Avenue and Wacker Drive. (112 E. Wacker Dr., cruisechicago.com ).

A CityPASS ticket discounts several downtown big attractions, including the Art Institute of Chicago, where major works by Monet, and Matisse, and Picasso, and Pollock are joined by the lower level Thorne Miniature Rooms gallery featuring exquisite tiny living (111 S. Michigan Ave., artic.edu ); and the Field Museum, named in honor of its first major benefactor, Marshall Field, the department-store magnate. Now one of the largest natural history museums in the world, one where visitors may meet Spinosaurus, the latest dinosaur in an amazing collection (1400 S. DuSable, fieldmuseum.org ).  

CityPASS also saves on admission to Skydeck Chicago and the city’s other vertigo testing observation deck, 360 Chicago at the top of the former John Hancock Center —  an unlovely black faced building built in 1965 — officially renamed 875 North Michigan Ave. in 2018. One thousand feet above the famed Magnificent Mile shopping stretch, TILT, a mechanized window, does exactly that, high above the street.

Skydeck Chicago includes an interesting history recalling how the city was defined by a devastating fire  — the Great Chicago Fire of 1871 destroyed most of the city, spurring the Great Rebuild that is the basis of this multilayered concrete and steel mass. There’s more on all that at the Chicago History Museum’s exhibition "City on Fire: Chicago 1871,} which runs until October 2024. It’s a family friendly, interactive, multimedia exhibit incorporating recorded stories from survivors of the fire (currently not discounted by CityPASS). 

There is yet another defining layer to The Loop besides up, down, and the bit in-between. Sitting in Miss Ricky’s American Diner in the Virgin Hotel (yes, Sir Richard Branson’s Virgin Hotel), or standing in the glass walled lobby of theWitt hotel on State Street, a layer so definitive of downtown Chicago is in full view: With great regularity, the elevated train trundles by, just overhead, both a part of the past and of the future, while being of great use in the now. 

Sweet dreams in the heart of The Loop

Fairmont Chicago — Millennium Park welcomes guests with its “inner circle” lobby bar, a great spot for a drink and some people watching; and the Columbus Tap, a casual eatery, but with good Fairmont culinary standards. Tucked in the basement,  Leaf Spa is a hidden gem, excellently staffed, and with a fun make your own scrub bar — guests may take their concoction home (from $215 per night, 203 N. Wabash Ave., fairmont.com ). 

Virgin Hotel, Chicago was the first property in the Virgin Hotels Collection brand. Opened in 2015, Miss Ricky’s American Diner has an Italian inspired dinner menu and all-American breakfast one — and train spotting! The clubby Cerise rooftop is the spot for drinks and far flung urban views. Rooms — a mix of mod dorm and airline inspired decor — are blessed with gorgeous Red Flower toiletries in the spacious showers (from $199 per night, 203 N. Wabash Ave., virginhotels.com/chicago ). 

St. Regis Hotel Chicago, from bottom to top, is a treat… or retreat. Opened in 2023, this luxury hotel standing so very tall where the Chicago River meets Lake Michigan, includes the 11th floor Miru restaurant where, each evening, there’s the “Champagne Sabrage” ritual on the adjacent terrace. Located on the tenth floor, the St. Regis Spa has purposeful pampering. Rooms are pricey, but for all the right reasons (from $700 per night, 401 East Wacker Drive, marriott.com ).

The Langham, Chicago retains the brand’s excellent Chuan Spa, where guests can indulge in signature Chinese medicine inspired wellness treatments, adjacent to  the pool and fitness center. Dine at Travelle on the hotel’s second floor; or relax in Pavilion, a gilded cage where “Afternoon Tea with Wedgwood,” the brand’s signature afternoon tea is served  (from $625 per night, 330 N. Wabash Ave., langhamhotels.com ).  

TheWit Chicago, a Hilton property in the Theater District, recently glammed up from the lobby to ROOF on theWit lounge, which has a glass retractable roof for those highly changeable seasons. The Spa @ theWit’s Flow massage uses expert hands to work travel worn muscles and joints with customizable modalities, and the State and Lake Chicago Tavern is a casual sports bar and restaurant (from $186 per night, 201 N. State St., hilton.com ).

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A tour of Ferris Bueller’s Chicago

Stuck at home? Take a trip through 1980s Chicago by revisiting this John Hughes classic.

If being stuck indoors while you practice social distancing has you pining for a day out on the town, dust off your copy Ferris Bueller’s Day Off and distract yourself with a nostalgic trip through 1980s Chicago. The movie was a “love letter” to the city from filmmaker John Hughes. “I really wanted to capture as much of Chicago as I could,” he said. “Not just in the architecture and landscape, but the spirit.”

Chicago isn’t just a backdrop for the beloved 1986 film. Places like Willis Tower, Wrigley Field, the Art Institute, and Lake Shore Drive played pivotal roles in the story—almost taking on lives of their own. And by capturing the city’s skyscrapers, cultural landmarks, streets, and people on film, Midwesterners were able to claim a piece of Hollywood for themselves.

Many of the sites featured in Ferris Bueller’s Day Off also were personally meaningful for Hughes. For instance, as a high schooler growing up in Northbrook, Illinois, the future director often escaped suburbia by wandering the halls of the Art Institute.

Here are some of the most iconic Chicago filming locations in the ’80s classic.

Cameron's House

Ferris’s loyal sidekick Cameron Frye lives in a modernist home designed by architect A. James Speyer located in Highland Park. The property’s glass-encased garage plays an important role in the movie. It’s the site where the precious 1961 Ferrari plummets down into the ravine. The North Shore home was on the market for five years before it finally sold in 2014 .

• Open in Google Maps

333 West Wacker

Just before the scene at Ferris' dad's office, the film focuses on the then-new 333 West Wacker Drive. The movie was shot in 1985, and the curved high-rise designed by Kohn Pedersen Fox Associates was completed just two years prior. The office tower was the epitome of cutting edge postmodern design at the time and it reflects the bend of the Chicago River in its glassy green facade.

View this post on Instagram A post shared by Jon Ferrera (@jferrera87) on Jun 5, 2016 at 4:25pm PDT

Glenbrook North High School

In the movie, Ferris and Cameron speed over to Glenbrook North in the collectible Ferrari to bust Ferris' girlfriend Sloane Peterson out of school. The concrete stairs Sloane walks down are still mostly the same today, and students occasionally recreate the scene. Glenbrook North was Hughes’s alma mater and also served as the setting for The Breakfast Club one year earlier.

View this post on Instagram A post shared by Lisie Cohen (@lisiecohen) on Oct 28, 2019 at 6:54pm PDT

In 1986, Millennium Park wasn’t a thing yet. Construction for the famous downtown park began in 1998. Aerial shots in the film show the sprawling train yards that would later get capped by lush gardens, playgrounds, art sculptures, and a Frank Gehry-designed bandshell.

Watching Ferris Buehler’s Day Off and forgot about how much awesome 80s footage of Chicago they had. Posted by Pat Hammond on  Friday, January 11, 2019

Lake Shore Drive

If you steal your dad’s Ferrari, how can you not cruise down Lake Shore Drive in the warm weather? It’s perfectly Chicago: skyscrapers on one side, and a clear blue lake on the other. The movie depicts Ferris, Cameron, and Sloane heading south on LSD with the John Hancock Center visible in the distance.

Italian Village

Italian Village on Monroe Street opened in 1927—it still serves up Tuscan fare today and represents one of the last old school Chicago dining rooms . After the trio exit Lake Shore Drive, there’s a shot of them driving past the restaurant’s iconic neon sign.

View this post on Instagram A post shared by #ChicagoHistory™️ (@chicago_history) on Nov 14, 2019 at 5:49pm PST

Parking Garage

The garage where the teens drop off the Ferrari (and where the “professional” parking attendant can’t help but take the convertible for a spin) is on Madison Street.

View this post on Instagram A post shared by Tony Taylor (@ignatiustaylor) on Dec 28, 2019 at 4:10pm PST

Wells Street

As soon as Ferris and company leave the parking garage, the attendant and his buddy hightail it out on the road. Hughes shot the beginning of their joyride on Wells Street, where the hot red Ferrari is framed by the familiar elevated CTA tracks.

View this post on Instagram A post shared by Dave Gil (@undercoverchef) on Sep 28, 2019 at 8:01am PDT

Willis Tower

The crew’s first stop downtown? The Sears Tower observation deck—now named the Willis Tower Skydeck. In the movie, Ferris mentions it’s the tallest building in the world which was true through the ’80s and into the ’90s. When the Petronas Towers in Malaysia were completed in 1996, the 1,451-foot tower lost its title. The iconic skyscraper managed to hold onto the claim of highest roof in the Western Hemisphere until 2019.

View this post on Instagram A post shared by Skydeck Chicago (@skydeckchicago) on May 23, 2016 at 9:00am PDT

Chicago Board of Trade

The Board of Trade shown in Ferris Bueller’s Day Off looks quite different today. In the ’80s, traders wore color-coded jackets, completed sales on paper, and yelled across the pit. Now, that same room is filled with digital screens, computers, and far fewer traders.

View this post on Instagram A post shared by Great Views (@views_515) on Jan 4, 2020 at 10:23am PST

Even if you’re Abe Froman the sausage king of Chicago, you won’t be able to get reservations at this fancy French restaurant because it simply doesn’t exist. The exterior shots of the fictional Chez Quis were a private home in Gold Coast which has since been remodeled and doesn’t feature the ivy-covered wall anymore. The interior shots were all filmed in Los Angeles.

View this post on Instagram A post shared by Timmy (@timmyo) on Oct 22, 2015 at 4:23pm PDT

Wrigley Field

What did generations of Chicagoans learn from Ferris? If you play hooky, go to a Cubs game. Of course, Hughes couldn’t resist adding in a scene set at one of the most beloved ballparks in the country. A neat detail you might have missed: Ferris catches a foul ball in this scene and later uses the same baseball to switch off the snoring soundtrack on his bedroom stereo at the end of the film.

View this post on Instagram A post shared by @ontheboomchicago on May 16, 2019 at 9:47am PDT

Art Institute of Chicago

Hughes choreographed a memorable montage at the Art Institute of Chicago, one of his favorite places in the city growing up. The three protagonists enter behind a group of school children, and then proceed to be goofballs throughout the massive museum. Then, Cameron comes face to face with Georges Seurat’s A Sunday on La Grande Jatte and has a moment . Meanwhile, Ferris and Sloane find themselves in front of Marc Chagall’s America Windows .

View this post on Instagram A post shared by Revolta da Pipoca (@revoltadapipoca) on Jan 9, 2020 at 10:28am PST

Daley Plaza

An impromptu musical number at the Von Steuben Day Parade shows the best of downtown Chicago—including the Picasso sculpture at Daley Plaza and Dearborn Street. Requiring nearly 10,000 extras, the scene brought the people of Chicago into the film and was Hughes’s favorite part of the entire movie.

View this post on Instagram A post shared by Katianna Lee (@katiannalee) on Feb 1, 2016 at 11:34am PST

Federal Center

While Ferris is serenading the Germans on a parade float, Cameron and Sloane take a walk through the plaza at the Mies van der Rohe-designed Federal Building and Post Office to talk about what happens after they graduate from high school. You can also spot Calder’s Flamingo sculpture —another beloved Federal Center landmark.

View this post on Instagram A post shared by @fvckpoliteness on Jan 8, 2020 at 9:39am PST

Glencoe Beach

As the trio head back to the North Shore, Cameron’s meltdown reaches a rock bottom when he realizes how many miles were put on his dad’s car. Ferris says, “I think Cameron may have blown a microchip or two,” and the three take a moment to regroup on the rocky wall overlooking Glencoe Beach.

View this post on Instagram A post shared by Chicago North Shore (@chicagonorthshore) on Nov 28, 2019 at 5:30am PST

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10 Best Chicago Private Tours to Book in 2024

Have you been wondering about chicago private tours you’ve come to the right place.

Chicago is a city with so much to offer and exploration of the Windy City through private tours is an incredible way to experience its unique and vibrant culture.

I lived in Chicago with my family for over 16 years and had the chance to take and give private tours showing off what makes the town so special. Of all the places we’ve traveled as a digital nomad family, Chicago is still one of my favorite cities.

I know all of the top spots for any great Chicago private tour: from Buckingham Fountain in Grant Park all the way up to the John Hancock Observatory, you’ll get to see many of Chicago’s must-see attractions on these curated tours.

Private tours offer a chance to hear the stories behind some of Chicago’s iconic architecture or get a taste of local cuisine at a restaurant off the beaten path.

There are plenty of great services providing private tours in Chicago , but every tour on this list is one I’d happily take myself (if I haven’t already) and/or recommend to friends and family visiting the Windy City. So let’s jump in!

My Top 3 Picks: Chicago Private Tours

Chicago Private Driver Tour

Hotel Pickup

Customizable Itinerary

Knowledgeable Driver/Guide

45-Min Chicago Skyline Helicopter Tour

See Chicago from above

Noise Canceling headphones

Free parking!

Lake Michigan Sailing Charter & Sightseeing

Coast Guard certified captain

BYOB & snacks

Groups up to 6 welcome

Best 10 Chicago Private Tours

1. chicago private driver tour.

  RATING:  5/5 Stars |   TOUR LENGTH:  3-4 hours |   Book Now!

Booking a guided tour of Chicago just for your group is the perfect way to have an exclusive luxury tour Chicago experience while making the most of your time in the Windy City!

First, you’ll be picked up directly from your hotel in a clean and comfortable Chicago private car, so you can start your sightseeing adventure right away. And there no need to book separate Chicago history tours!

Your guide will fill you in on all the history and stories of Chicago as you drive around, making stops at highlights like Lincoln Park Conservatory , Millennium Park, Museum Campus, and other notable attractions.

See more of the city in a short amount of time without having to worry about navigating yourself or being stuck with long waits between locations. And if you want to see something that isn’t part of the tour, just tell your guide!

Key Essentials

Professional local guide/driver

Private transportation

Pick up at your Downtown Hotel

Stroller/wheelchair accessible

All ages welcome

Infant seats available

Check Rates and Availability!

2. 45-Minute Chicago Skyline Helicopter Tour

  RATING:  5/5 Stars |   TOUR LENGTH:  45 Minutes |   Book Now!

Soar high above the Windy City on a private 45-minute Chicago Skyline Helicopter Tour. Enjoy sweeping views of Chicago, including Navy Pier, Wrigley Field, Millennium Park , John Hancock Center, and Willis Tower.

This is the perfect way to celebrate any special occasion with someone special – this tour can accommodate up to three people comfortably!

Plus, you get the use of noise-canceling headsets so you can hear your pilot clearly as they take you on an unforgettable journey through the skies of Chicago. And you’ll get complimentary parking!

Whether you’re looking for a unique date night experience or just something to do with friends and family, this helicopter tour promises breathtaking views and an unforgettable adventure!

All Fees and Taxes included

Live commentary on board

Noise canceling headsets

Free Parking

Free photos of and in front of the helicopter!

Wheelchair/stroller accessible

Individual passengers must weigh less than 260 lbs

3. Lake Michigan Sailing Charter & Sightseeing Tour

  RATING:  5/5 Stars |   TOUR LENGTH:  2 hours |   Book Now!

Experience the wind in your hair and the sun on your face as you explore Lake Michigan on a private sailboat. You and up to five other invited guests will have exclusive use of the boat, complete with captain and crew.

With BYOB allowed, bring along your favorite beverages (just no glass containers) to enjoy while taking in the sights of Chicago’s striking skyline. This is one of my favorite ways to spend an afternoon in Chicago!

Your captain can provide narration about different landmarks along the way, but if you’d like to customize the itinerary to suit your group’s interests, just let him know.

Plus, if anyone wants to take a turn at the helm, they can! Don’t forget a Bluetooth-enabled device so that you can play your tunes while out on the lake. There’s truly nothing quite like sailing away and feeling completely free!

Professional US Coast Guard licensed captain

Use of Bluetooth speakers

All applicable taxes

Bring seasickness medicines if needed

Get Dramamine for everyone! There’s even a chewable version available for kids.

4. History, Culture, and Architecture Walking Tour

  RATING:  4.8/5 Stars |   TOUR LENGTH:  2.5 hours |   Book Now!

From iconic architecture to tasty treats, there are plenty of unique experiences that will make your visit to The Windy City unforgettable. This private guided tour can help you explore the Loop and get around like a local.

You’ll have the opportunity to see some of the greatest hits of Chicago, such as incredible old and new buildings, stunning river views, and much more. You’ll also enjoy some classic snacks like Chicago-style popcorn and homemade chocolate.

You may also want to make time for visiting some of Chicago’s beautiful lakefront parks or museums so that you can feel the energy and buzz of this magnificent city.

No matter your interests, booking a private tour is a great way for you to experience all that Chicago has to offer. With an experienced guide leading the way, you’re sure to have an experience full of memories that will last a lifetime.

English-speaking guide

Popcorn tasting

Chocolate tasting

Eco-certified, carbon-neutral tour operator

Tour is available in groups or private, so be sure to choose the private option when booking!

5. Private Chicago Highlights Driving Tour

  RATING:   5/5 Stars |   TOUR LENGTH:  3 hours |   Book Now!

Take this private tour of Chicago and discover the beauty and history of some of the city’s most iconic monuments.

Tour the vibrant neighborhoods like The Loop, River North, Magnificent Mile (Michigan Avenue), Streeterville, Gold Coast, and more with your own private driver-guide and vehicle. You can even go past the Chicago Art Institute!

Get up close to towering skyscrapers (some designed by Louis Sullivan!) in awe, explore beautiful architecture, and immerse yourself in the vibrancy of the city.

Plus with round-trip hotel transport included as well as bottled water, you don’t have to worry about transportation or hydration! Experience Chicago’s top sights with an expert local guide who provides you with personalized service.

Downtown Chicago hotel/port pickup and drop-off

PrivateDriver/Guide

3-12 participants

Stroller accessible

6. Customized Private Walking Tour in Chicago

  RATING:   5/5 Stars |   TOUR LENGTH:  2 hours |   Book Now!

One of my favorite ways to experience Chicago is through a customized private walking tour. With this best tour in Chicago by foot, you get to immerse yourself in the Windy City and its culture like never before!

With your knowledgeable guide, create an itinerary that meets all your individual interests, whether it’s history, architecture, street art, or Chicago’s food scene. And get recommendations for where to explore once the tour ends!

Art, food, shopping, and architecture fans can enjoy Chicago sightseeing tours tailored just for them! But no matter which type of tour you choose, every tour is different and tailored just for private groups of up to 6 people.

With a knowledgeable, private guide at hand, your day will be filled with amazing adventures that will give you memories that last a lifetime!

CTPA Licensed Guide

Hotel pickup is available or meet at a location of your choice

Tours are available in English, French, and Dutch

Wheelchair and stroller accessible

7. Private Walking Food Tour With Secret Foods

Your private walking food tour of Chicago is guaranteed to be the perfect way to explore the city’s most delicious eats! Delight in deep-dish pizza before your guide shows you sweet and savory treats that many visitors overlook.

As you go, you’ll get to learn about the history, architecture, and culture of this vibrant city. You’ll also enjoy enough treats and samples for a generous lunch along the way.

Wander through downtown Chicago with an expert guide who knows all the hidden gems. Your private tour gives you access to some of Chicago’s greatest culinary secrets without any crowds or long lineups.

For an unforgettable experience in one of America’s best cities for foodies, book this private walking foodie tour today! And be sure to show up hungry!

Deep Dish Pizza with Sausage

Gourmet Popcorn

Chicago-style Hot Dog

Italian Beef Sandwich

A delicious Secret Dish

8. All-Inclusive Chicago Foodie Tour: Windy City Favs

  RATING:   5/5 Stars |   TOUR LENGTH:  4 hours |   Book Now!

Treat your taste buds to all the best Chicago has to offer with a private foodie tour of the city. This excursion Chicago offers all my local favorites, so you’re sure to enjoy it!

From deep-dish pizza and Italian beef sandwiches to hot dogs, and donuts, you’ll have a hard time deciding which tastes better. All while taking in some of the city’s most iconic sites like the Wrigley Building and Magnificent Mile.

Get an insider look at Millennium Park and The Rookery Building, among other landmarks. These local spots provide an authentic glimpse into the culture and history of this great city.

Your private guide will not only show you around the historic sites but also share stories and facts about each location that make it unique. Don’t miss your chance to explore Chicago’s top sightseeing spots while feasting on its famous eats !

An Uber ride

English speaking tour guide

All tastes and fees

Bottled water

1 Portillos hotdog

1 small Garrett’s popcorn

1 6-inch Al’s Italian Beef sandwich

1 slice of deep-dish pizza

1 Do-rite Donut

9. Evening Sail in Chicago w/Navy Pier Fireworks

One of my favorite ways to spend an evening in Chicago is sailing while watching the Navy Pier Fireworks!

Treat yourself to an unforgettable experience on a private sailboat cruise that will take you along the beautiful lakefront of the iconic city. Enjoy a breathtaking view of the skyline as you watch the incredible fireworks from Navy Pier.

You and up to five others will have two hours to explore, customize your trip and make memories along the way.

Your U.S. Coast Guard licensed captain will be sure to provide a safe and intimate voyage, with your choice of music, route, and guest list so you can create a personalized evening worth remembering!

Bring Dramamine if anyone in your party is prone to seasickness

10. Chicago Lakefront Electric Bike Tour

  RATING:   5/5 Stars |   TOUR LENGTH:  1-2 hours |   Book Now!

Make your Chicago experience one to remember with a private electric bike tour. Explore the city like never before, zipping along Lake Michigan and viewing the Chicago skyline from picture-perfect spots.

On your journey, you’ll see the iconic Buckingham Fountain, Field Museum, Adler Planetarium, and other landmarks.

Get up close and personal with the architecture, landmarks, and history of Chicago on this private electric bike tour. Your personal guide will provide an immersive experience as you ride along effortlessly on an e-bike.

Perfect for those 12+ who can ride their own full-size bike, this tour offers an unforgettable way to explore Chicago’s waterfront sights in record time.

Use of bicycle and helmet

Bottled water & snacks provided

Participants 12+ only

Infant bike seats and tagalongs are not available

FAQs About Chicago Private Tours

Do you still have questions about private Chicago tours? Here are answers to some frequently asked questions.

How much is a tour guide in Chicago?

The cost of the tour depends on the size and type of tour you select. Group tours generally cost less than private tours, but they may not offer as much customization or personal attention.

Private tours are usually more expensive, but you will have a guide that is dedicated to providing you with a customized experience with personalized attention.

What is a private tour?

Creating a customized tour of any destination just for your group is a great way to ensure that you and your fellow travelers get the most out of your experience.

A private guided tour will allow you to tailor the itinerary to your exact needs, allowing more time for activities that interest your group and providing insider knowledge from our expert tour guides.

Are private tour guides worth it?

Yes, private tour guides are definitely worth it! Private tours provide a personalized experience that can’t be found in large group tours. With private tour guides, tourists have the chance to tailor the tour to their specific interests and needs.

Private tour guides also give tourists access to exclusive information and insights about the destination they are visiting that they wouldn’t get with traditional group tours.

What is the best way to tour Chicago?

The best way to tour Chicago is to book a private tour with a knowledgeable and experienced guide. This will ensure that you have the most comprehensive and enjoyable experience possible, as you’ll receive advice on the city’s top attractions tailored to your interests.

Furthermore, private tours allow for much more intimate and personal interactions than public group tours can provide. You’ll also be able to ask questions and get more in-depth information about the city’s history, culture, and architecture.

Why choose a private tour?

Private tours give you and your group exclusive access to the sights and attractions, allowing for a more personalized experience. Instead of having to stick to a generalized itinerary, your tour guide can tailor the tour based on your interests and preferences.

Depending on the size of your group, you may even be able to get time with the guide all to yourself! Private tours also come with additional benefits that are not available with regular group tours, such as priority booking for popular attractions like museums.

Should I get a tour guide?

Traveling can be an incredible experience for those who are looking to explore new places around the world.

But if you want to make sure that your trip is as enjoyable and memorable as possible, it’s important to consider how a tour guide can help you get the most out of your travels.

Are private tours safe?

A private tour with excellent reviews is definitely the way to go for extra peace of mind. Private tours will give you access to lesser-known spots, allowing for a more intimate and unique experience of the destination.

It’s also great for having some quality time with your family or friends without having to worry about large crowds or disturbances. Plus, reading reviews by previous customers can give an indication of the quality of the tour and help you pick the right one.

So yes, definitely choose a private tour with excellent reviews for that bonus peace of mind!

Is it better to travel with a tour guide or alone?

Traveling with a tour guide can definitely add value to your trip, depending on your goals. Tour guides can help you learn more about the culture and history of the places you visit, and provide valuable insights that you wouldn’t get otherwise.

On top of that, they often know the best places to eat, shop and find entertainment. They can also provide safety advice and show you around in areas where it might be difficult to navigate or communicate without knowing the language.

What is the difference between a group tour and a private tour?

Group tours are organized trips that involve traveling with a larger group of people. Typically, everyone on the tour follows the same itinerary and visits the same attractions. There’s no customization but the tradeoff is it’s generally cheaper.

Private tours allow for more personalization and freedom to tailor your experience. They may include private transportation, customized itineraries, and specialized guides. Private tours also tend to be more expensive than group tours due to their personalized nature.

The Chicago Private Driver Tour is the best choice for an exclusive, luxurious experience with maximum flexibility!

Final Thoughts: Private Guided Tours Chicago

Chicago private tours are the best way to make sure you see everything in the Windy City that you want to.

With so many unique districts and attractions, personal tours allow you to tailor your experience to what appeals most to you.

With an experienced guide, it’s easy to make sure you get a great view of every stop on your list. From stunning views of Lake Michigan to the endless nightlife of Wicker Park, there’s something for everyone in Chicago.

No matter how much time you have in Chicago, there’s no better way to ensure you get the absolute most out of the city than with a private best Chicago tour.

So don’t wait any longer – check out one of these amazing options and book one of the private tours Chicago offers today!

Each of these experienced Chicago tour guides can show you all the sights that this incredible city has to offer and ensure that your experience is as amazing as possible.

Looking for other fun things to do in Chicago? While there aren’t any private options, the Chicago Architecture Tour River Cruise is one of my favorite group tours in Chicago!

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The post 10 Best Chicago Private Tours to Book in 2024 appeared first on Our Offbeat Life .

Time to fill this bad boy with great products like gadgets, electronics, housewares, gifts and other great offerings from Groupon Goods .

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90-Minute Chicago Architecture Boat Tour & Cruise for One, Two, Three, or Four (Up to 41% Off)

$29 for 90-minute chicago architecture boat tour for one, $58 for 90-minute chicago architecture boat tour for two, $87 for 90-minute chicago architecture boat tour for three, $116 for 90-minute chicago architecture boat tour for four.

• Instant: Great for last-minute gifts. Simply print or send the voucher after purchase.
• Customizable: Personalize the message and appearance to make your gift truly special.
• Exchangeable: Hassle-free returns and exchanges for the giftees.

Picturesque Chicago river cruise is paired with architecture and history lessons about the city’s most popular landmarks

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About This Deal

General Information

• What’s included: a leisurely architecture boat tour of downtown Chicago
• Departure times: Click here to see the schedule and availability as well as information on parking and directions.
• Alcoholic and nonalcoholic beverages and snacks are available for purchase onboard.
• Kids aged 3 and younger ride free, but must be included in your online reservation on the merchant website.
• Parking: located right next to the marina.
• Vessel: full-service bathrooms, bars, and staff assist with passenger's needs

The Best Way to Visit Chicago

Chicago is famous for its architecture, and the best way to see it is on a cruise down the Chicago River. Each architecture river tour is narrated by a professional guide who leads passengers down the Chicago River to discover the city’s most renowned landmarks. In addition to historical insight into well-known structures such as the Civic Opera House, Trump Tower & the Merchandise Mart, passengers will also get a chance to learn about current and upcoming developments. The Architecture River Cruise navigates the three primary branches of the river including the main branch to Navy Pier, the north branch to Goose Island, and the south branch to Chinatown.

• Discover the story of Chicago and learn about its architectural wonders.
• In-depth commentary from the tour guide provides insights on different artistic styles throughout the decades.
• Get a glimpse at the buildings from the ship’s open-air upper deck or its enclosed, air-conditioned main deck.
• The ship’s 360° viewing capabilities allows you to admire incredible city panoramas from all sides
• Take wonderful skyline photos from your unique onboard position.

⚓ Departure Location: 900 South Wells St., Chicago, IL 60607 ⚓

• Please enter 900 S Wells Chicago, IL 60607 to your GPS for directions to the boat dock. Go through the parking lot behind the River City condominium building. The parking lot is located across from the soccer field on 9th St and Wells.

How to Schedule

• After purchasing your voucher, you'll receive instructions and a link to schedule the date and time of your tour
• Available dates and times can be viewed here .
• Please check schedule prior to purchase to confirm availability of your desired tour time

Reviews from Happy Participants

• If you are visiting Chicago and want something awesome to do. Don’t skip out on this great attraction. Great thing about the boat we were on was air-conditioned at the bottom. Our tour guide was very knowledgeable and gave us a lot of insight on the different architecture in Chicago that we seen. This is a 5-STAR a must-go!
• The best boat tour ever! I and my friend were so happy that we did this. Definitely learned a lot while enjoying the amazing views. I know there are tons of seemingly the same kind of tour out there though, but this is the one that you’d want to join as they offer a further trip to the north and provide rich history and information. It’s 10 out of 10. Highly recommended!
• My mom and I played tourists the day we went and loved it!! If you’re coming to Chicago we highly recommend this company! Our guide was wonderful and she added fun and excitement to the tour!! What a fun day hanging out with my mom!

About Tours and Boats

Chicago's decorated past lives on through captivating stories told by the knowledgeable guides at Tours and Boats. These Windy City experts usher groups of travelers to myriad landmarks while sharing anecdotes that paint a vibrant picture of the city's history. During the company's sightseeing river cruises, their boats float by well-known structures such as the Merchandise Mart, Navy Pier and Willis Tower while passengers learn about the city's famed architecture.

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