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107 results | All Chicago Tours

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Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-5
2457
Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
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  • 2 hours
  • Free Cancellation
From
USD35.00
From
USD35.00

Chicago Walking Tour: Historic Treasures of Chicago

Chicago Walking Tour: Historic Treasures of Chicago

star-5
45
Get an insider's introduction to Chicago's most celebrated buildings during this architecture-focused walking tour of Michigan Avenue and State Street. Revisit the heyday of the skyscraper and visit stunning, Art Deco-era interiors, from the Palmer House Hotel to the Chicago Cultural Center. Admission to the Chicago Architecture Center is included, with an introduction by the docent.
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  • 2 hours
  • Free Cancellation
From
USD30.00
From
USD30.00

Chicago Favorites Ultimate Food & Walking Tour

Chicago Favorites Ultimate Food & Walking Tour

star-5
384
Stroll through downtown Chicago on this walking food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, plus chocolates and pastry. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. Upgrade your tour to include three pours of local craft beer.
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  • 3 hours
  • Free Cancellation
From
USD74.99
From
USD74.99

Chicago Architecture Walking Tour: Dazzling Interiors™ of the Loop

Chicago Architecture Walking Tour: Dazzling Interiors™ of the Loop

star-5
337
See the overlooked highlights of Chicago’s Loop district with a 2-hour walking tour that takes in the best of the bustling, vibrant neighborhood’s inside spaces. Get behind the façades to explore stunningly designed interiors as you follow a specially-designed route with an experienced guide. Learn about the city’s architecture, art and history while visitng a side of Chicago that’s beyond the tourist trail, and experience the Windy City with a local perspective.
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  • 2 hours
  • Free Cancellation
From
USD35.00
From
USD35.00

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

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

star-5
235
An excellent choice for first-time visitors, this tour provides a comprehensive overview of the city and hits on both classic attractions and little-known sites. Beginning at the Chicago Theatre, work your way to the Chicago Pedway, an elaborate network of underground tunnels used by locals and commuters. Stroll the Chicago Riverwalk and the Magnificent Mile, then embark on a food tour to taste some of the city’s famous foods.
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  • 5 hours
  • Free Cancellation
From
USD104.00
From
USD104.00

Chicago Architecture River Cruise

Chicago Architecture River Cruise

star-5
7504
Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
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  • 1 hour 15 minutes
  • Free Cancellation
From
USD46.87
From
USD46.87

Lake Michigan Sightseeing Cruise
Likely to Sell OutLikely to Sell Out

Lake Michigan Sightseeing Cruise

star-4.5
348
Take in iconic views of the beautiful Chicago lakefront and its many landmarks during this Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laid-back ride, enjoying panoramic views of the Windy City's skyline from a unique perspective. Along the way, you'll listen to informative commentary and take in views of the John Hancock Center and Willis Tower, along with many other landmarks. Plus feel free to bring your own lunch or grab a drink at the onboard bar, during your ride.
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  • 40 minutes
  • Free Cancellation
From
USD28.34
From
USD28.34

Big Bus Chicago Hop-On Hop-Off Tour

Big Bus Chicago Hop-On Hop-Off Tour

star-4
996
Don’t spend time figuring out what to see in Chicago and how to get there—this hop-on hop-off tour provides a mapped-out itinerary of the city's top sights. With several strategically located stops, the tour allows you to explore the Windy City at your own pace. See the world-class Art Institute and landmark skyscrapers, while audio commentary onboard gives you insight into the city's colorful history.
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  • 2 hours
  • Free Cancellation
From
USD44.99
From
USD44.99

Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4.5
1343
Explore Chicago's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.
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  • 1 hour 30 minutes
  • Free Cancellation
From
USD46.00
From
USD46.00

90-Minute Chicago River Architecture Tour
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90-Minute Chicago River Architecture Tour

star-4.5
1634
Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.
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  • 1 hour 30 minutes
  • Free Cancellation
From
USD42.00
From
USD42.00

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

star-4.5
218
Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.
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  • 45 minutes
  • Free Cancellation
From
USD25.00
From
USD25.00

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

star-5
349
Chicago dogs, deep-dish pizza, cupcakes and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following an informative guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Gold Coast, Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and Chicago’s Lakefront trail. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.
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  • 4 hours
  • Free Cancellation
From
USD89.99
From
USD89.99

Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship
Likely to Sell OutLikely to Sell Out

Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship

star-4.5
196
Escape the bustle of the city on a sailboat tour through Lake Michigan with a convenient departure from Navy Pier. The cruise offers plenty of frame–worthy photo opportunities, including sweeping views of the Chicago skyline rarely seen by visitors. As a popular choice for both locals and visitors, your experience is guaranteed to be family–friendly and tailored to your needs. Select from Pirates and Maritime Stories Sail at 1pm, Skyline/Architectural Theme at 3pm and 5pm, and Skyline Sunset Sail at 7pm. This sail is approximately 75 minutes. The ship leaves promptly at the scheduled time, please allow for time to park, off the pier if necessary.
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  • 1 hour 15 minutes
  • Free Cancellation
From
USD49.00
From
USD49.00

Underground Donut Tour: Chicago's First Donut Tour
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Underground Donut Tour: Chicago's First Donut Tour

star-5
386
Sample some of the Windy City’s tastiest donuts on this Underground Donut Tour, celebrating the magic of Chicago’s tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit to some of Chicago’s tastiest donut purveyors, offering a chance to savor all of your favorite varieties, on the city's only donut-themed excursion. All tastings are included, and vegan, gluten-, and nut-free options are also available.
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  • 2 hours
  • Free Cancellation
From
USD40.00
From
USD40.00

Chicago Lake and River Architecture Tour
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Chicago Lake and River Architecture Tour

star-4.5
614
Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.
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  • 1 hour 30 minutes
  • Free Cancellation
From
USD42.00
From
USD42.00

Chicago Sunset Cruise

Chicago Sunset Cruise

star-4.5
212
Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel in the heart of the Magnificent Mile, and cruise along the Chicago River, where your guide will point out architectural highlights. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.
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  • 1 hour 30 minutes
  • Free Cancellation
From
USD42.00
From
USD42.00

Chicago Walking Tour: Art Deco Skyscrapers Loop

Chicago Walking Tour: Art Deco Skyscrapers Loop

star-4.5
85
Admire the incredible façades and intricate interiors of the Windy City's 1920s art deco and art moderne buildings during this architecture walking tour of Chicago. Uncover the history of Chicago art deco architectural along with the city's influential role in the development of this iconic artistic style, as you get an up close and personal look at its wealth of gorgeous period buildings. This art deco Chicago walking tour also includes a certified guide.
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  • 1 hour 30 minutes
  • Free Cancellation
From
USD30.00
From
USD30.00

Frank Lloyd Wright Robie House Admission
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Frank Lloyd Wright Robie House Admission

star-4.5
23
Discover one of Chicago’s top architectural marvels when you explore Frank Lloyd Wright’s UNESCO-listed Frederick C. Robie House, located right on the University of Chicago’s campus. Considered a masterpiece of Prairie School architecture, the building is famed for its cantilevered roof and rich wood details. Save money when you book tickets to the house in advance; call ahead to reserve a space on one of the museum’s frequent, small-group public tours.
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  • 1 hour
  • Free Cancellation
From
USD27.00
From
USD27.00

Chicago's Gold Coast Hidden History: A Self-Guided Audio Walk

Chicago's Gold Coast Hidden History: A Self-Guided Audio Walk

star-4.5
4
Amy Bizzarri, author of 111 Places in Chicago That You Must Not Miss, takes you on a fascinating self-guided audio tour of hidden historical spots in Chicago's gilded Gold Coast. Peep behind the gates of the original Playboy Mansion, walk along a wooden block-paved alley, sip a Faster Pussycat in Chicago's oldest piano bar and more as you enjoy a delightful walk through time in this exclusive Chicago neighborhood. The starting point is the Chicago History Museum, located at 1601 N. Clark Street. The tour is ready whenever you are and the audio plays automatically at exactly the right time and place using your smartphone's GPS and the VoiceMap mobile app, which also works offline.
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  • 50 minutes
From
USD5.34
From
USD5.34

Discovering Vintage Chicago: A Self-Guided Audio Tour of the Loop

Discovering Vintage Chicago: A Self-Guided Audio Tour of the Loop

star-1
1
Take a walk back in time through the history of Chicago's Loop on this app-enabled tour. After downloading the app and tour to you smartphone, you and your party will listen to author Amy Bizzarri, an author and expert in Chicago history, as she leads you through walking tour of the city. The GPS-enabled tour will trigger commentary at just the right times, and you can stop and start whenever you like for a flexible experience that lets you move at your own pace. Highlights include Daley Plaza, the Chicago Theater, Berghoff Restaurant, and the Art Institute of Chicago.
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  • 50 minutes
From
USD5.34
From
USD5.34

Chicago Loop Secret Food Tour with Private Tour Option

Chicago Loop Secret Food Tour with Private Tour Option

star-5
264
Explore Chicago's buzzing food scene with a small group on this small group walking tour. Stroll around the 'Loop', stopping at hidden gems and hearing tales of the city from your guide. Taste classic Chicago foods, from deep-dish pizza to dipped Italian beef sandwiches.
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  • 3 hours
From
USD84.53
From
USD84.53

Chicago Loop Walking Tour

Chicago Loop Walking Tour

star-5
47
Step into the heart of Chicago with this 2-hour walking tour of the Loop. You’ll meet your local guide at the Chicago Cultural Center and make your way through the city’s downtown. Stop to check out the elevated “L” train, buildings by Burnham and Sullivan, busy commercial centers and lesser-known quiet corners of this vibrant area. You’ll come away with a deeper sense of Chicago’s rich history and architecture.
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  • 2 hours
  • Free Cancellation
From
USD60.00
From
USD60.00

Holiday Hike Chicago-Style: Festive Food & Walking tour

Holiday Hike Chicago-Style: Festive Food & Walking tour

star-5
25
Stroll through Chicago's winter streets, lit up for the holidays, on this gourmet walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows on State Street, and ice skating at Millennium Park. Sample generous tastes of classic Chicago foods and holiday treats as you walk. Seasonal craft beer tastings help you stay warm and toasty; please note this tour operates in all weather conditions, so dress appropriately.
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  • 3 hours
  • Free Cancellation
From
USD69.99
From
USD69.99

Chicago Walking Tour: Modern Architecture

Chicago Walking Tour: Modern Architecture

star-5
16
Embark on a walking tour of Chicago's more-recent architecture heritage with a 2-hour stroll highlighting the city's modern, postmodern, and international structures. Especially known for its architectural originality, Chi-town boasts everything from the elegant metal and glass tower of One South Dearborn to the Harold Washington Library, with its Beaux-Arts inspired exterior. Your guide will highlight these and other unique buildings, relaying background on their individual histories and construction en route.
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  • 1 hour 30 minutes
  • Free Cancellation
From
USD30.00
From
USD30.00

Filters

What people are saying about Walking Tours in Chicago

star-5
Gangsters and Ghosts Tour in Chicago
"Wonderful way to see through the city and go for a lovely walk! We went with Sarah and she was great to listen to and hear the history and stories of the city. It was affordable and the weather wasn’t too terrible. Our group was small which made it better to hear and ask questions!"..."
star-5
Chicago Walking Tour: Historic Treasures of Chicago
"Very interesting and well-lead tour of some stunning Chicago architecture. Thank you to docent Susan!"..."
star-5
Chicago Favorites Ultimate Food & Walking Tour
"Awesome food. Friendly and extremely knowledgeable guide! Visited great restaurants and lovely sights all over that we wouldn’t have known about otherwise!"..."
star-5
Chicago Architecture Walking Tour: Dazzling Interiors™ of the Loop
"Adam knew his stuff! We went into buildings that I might have just passed by, not expecting what was inside. It was very surprising in some cases! Lots of fun!"..."
star-5
Chicago in a Day: Food, History and Architecture Combo Walking Tour
"This was the perfect tour! Our tour guide “Dash” was awesome. So knowledgeable of the city’s history and he set the right pace for our family. We got to see the inside of historic buildings, many of the city’s landmarks and sampling some of the city’s famous foods. Highly recommend!"..."
star-5
Chicago Architecture River Cruise
"Best tour! Awesome to learn more about the city and see all of the buildings. Our guide Sam did a fantastic job!"..."
star-5
Lake Michigan Sightseeing Cruise
"Good Overall Experience. The crew members were really friendly and helpful. One of them even offered to take our pictures, that was so thoughtful. Nice views of the Chicago skyline."..."
star-5
Big Bus Chicago Hop-On Hop-Off Tour
"Great way to see the city then decide where you would like to spend more time. It was great to have the headphones so you could hear all the highlights."..."
star-5
Chicago Crime and Mob Bus Tour
"Very enthusiastic and intelligent tour guide lady Great tour and city sightseeing We recommend for all that visit Chicago"..."
star-5
90-Minute Chicago River Architecture Tour
"Excellent tour! We loved our guide, Kay. She was fun, entertaining, and informative! I learned a lot more than I expected about the architecture of Chicago. I highly recommend this tour!"..."
star-5
45-Minute Chicago River Architecture Tour from Magnificent Mile
"Matthew did an awesome job. Matthew was very engaging, knowledgeable and had a lot of charisma. The Chicago architecture is breathtaking. So very glad we took this tour."..."
star-5
Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour
"This excursion was the highlight of our trip to Chicago. Loved it! They are making me type more before sending this so I added this sentence Bhaaa."..."
star-5
Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship
"The crew were engaging and made certain safety was practiced. The history lesson was great… but a megaphone would have been a great asset in order to hear everything. Great trip that all must go on while in Chicago!"..."
star-5
Underground Donut Tour: Chicago's First Donut Tour
"Nick was a great tour guide. We really enjoyed our tour! The donuts were delicious, it was fun to try each of the 4 donut shops and to hear the background stories behind each"..."
star-5
Chicago Lake and River Architecture Tour
"Kenneth was amazing. Highly recommend his chores. Extremely knowledgeable, articulate, entertaining, personable, and more. I would do this exact trip again and again."..."
star-5
Chicago Sunset Cruise
"Great time and staff guide very friendly. Company on time. We high recommended. Beautiful city chicago."..."
star-5
Chicago Walking Tour: Art Deco Skyscrapers Loop
"Jonelle was an amazing guide! She gave a great educational tour of the pivotal Chicago Art Deco skyscrapers and I’m so glad we went. Highly recommended!"..."
star-5
Frank Lloyd Wright Robie House Admission
"Excellent, information tour. It was fascinating to learn both the stories of the architecture and the residents."..."
star-5
Chicago's Gold Coast Hidden History: A Self-Guided Audio Walk
"I generally don't like group tours, so having this option is wonderful. It felt like having your own private tour guide. In this time of Covid-19, this gae us a nice way to get out of the house. The Zebra Lounge wasn't open, but just around the corner there was a street closed off to allow for outdoor dining/social distancing. The museum of surgery was open, and we spent time there as well as Restoration Hardware."..."
star-5
Chicago Loop Secret Food Tour with Private Tour Option
"Denise provided a wonderful entertaining and educational experience. The pizza, Italian beef sandwich and surprise dessert were delicious. Thanks for the terrific tour."..."
star-5
Chicago Loop Walking Tour
"Kevin was fantastic. So knowledgeable and fun. We learned so much about Chicago’s amazing architecture and history"..."
star-5
Holiday Hike Chicago-Style: Festive Food & Walking tour
"Very good tour. Come hungry as we had just eaten breakfast and opened the tour with deep dish pizza and then followed that by Italian beef."..."
star-5
Chicago Walking Tour: Modern Architecture
"A challenge during Covid 19 restrictions, the tour guide found good ways to share her excellent information and make us comfortable."..."

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What are the best Walking Tours in Chicago?
Q:
What Walking Tours in Chicago are 1 hour or less?
Q:
What Walking Tours in Chicago are taking additional safety precautions?
Q:
What Walking Tours in Chicago are good for avoiding crowds?