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93 results | All Chicago Tours

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Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-5
2196
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
$35.00
From
$35.00

Chicago Favorites Ultimate Food & Walking Tour

Chicago Favorites Ultimate Food & Walking Tour

star-5
297
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
$69.99
From
$69.99

Chicago Architecture Walking Tour: Dazzling Interiors™ of the Loop

Chicago Architecture Walking Tour: Dazzling Interiors™ of the Loop

star-5
303
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
$33.00
From
$33.00

Underground Donut Tour: Chicago's First Donut Tour

Underground Donut Tour: Chicago's First Donut Tour

star-5
328
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
$30.00
From
$30.00

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

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

star-5
169
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
$104.00
From
$104.00

Chicago Architecture River Cruise
Likely to Sell OutLikely to Sell Out

Chicago Architecture River Cruise

star-5
7018
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
  • Free Cancellation
From
$40.33
From
$40.33

90-Minute Chicago River Architecture Tour

90-Minute Chicago River Architecture Tour

star-4.5
1367
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
$40.00
From
$40.00

Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4.5
1150
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
$46.00
From
$46.00

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour
Likely to Sell OutLikely to Sell Out

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

star-5
334
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
$84.99
From
$84.99

45-Minute Chicago River Architecture Tour from Magnificent Mile

45-Minute Chicago River Architecture Tour from Magnificent Mile

star-4.5
145
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
$23.00
From
$23.00

Chicago Lake and River Architecture Tour

Chicago Lake and River Architecture Tour

star-4.5
562
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
$40.00
From
$40.00

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

star-5
51
Get off the beaten path to experience some of Chicago's best street art on this immersive tour. With a guide in the lead, you can leave the navigation to them and simply take in the scenery. Listen to in-depth commentary focused on the street-art community, the artists, and the history and meaning behind the art.
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  • 2 hours
  • Free Cancellation
From
$26.67
From
$26.67

Big Bus Chicago Hop-On Hop-Off Tour

Big Bus Chicago Hop-On Hop-Off Tour

star-4
925
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
$26.10
From
$26.10

Chicago Sunset Cruise

Chicago Sunset Cruise

star-4.5
175
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
$40.00
From
$40.00

Behind-the-Scenes Tour of Historic Chicago Theatre

Behind-the-Scenes Tour of Historic Chicago Theatre

star-4.5
21
Tour the historic Chicago Theater, a must-see city landmark, with a guide providing in-depth commentary. You'll get the most out of your visit by traveling with a guide and get access to some areas of the theater that the public never sees. Learn about its architecture, history, and famous performers throughout the years.
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  • 1 hour
  • Free Cancellation
From
$18.00
From
$18.00

Chicago Craft Brewery Barrel Bus Tour
Likely to Sell OutLikely to Sell Out

Chicago Craft Brewery Barrel Bus Tour

star-4.5
51
Learn about Chicago’s brewpub scene and taste different types of craft beer on this guided brewery tour. Visit unique breweries for craft beer samples plus an additional brewing production facility for an in-depth tour. Discover the science behind the brewing process, complete with step-by-step procedures, and enjoy plenty of beer samples throughout the tour. Round-trip transportation in a Prohibition-era-styled barrel bus is included.
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  • 3 hours 30 minutes
  • Free Cancellation
From
$89.60
From
$89.60

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
$5.34
From
$5.34

Discovering Vintage Chicago: The Loop Walking Audio Tour

Discovering Vintage Chicago: The Loop Walking Audio Tour

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
$5.34
From
$5.34

Chicago Loop Secret Food Tour with Private Tour Option

Chicago Loop Secret Food Tour with Private Tour Option

star-5
261
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
$84.53
From
$84.53

Chicago Walking Tour: Art Deco Skyscrapers

Chicago Walking Tour: Art Deco Skyscrapers

star-4.5
81
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
$30.00
From
$30.00

Chicago Loop Walking Tour

Chicago Loop Walking Tour

star-5
40
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
$42.67
From
$42.67

Holiday Hike Chicago-Style: Festive Food & Walking tour

Holiday Hike Chicago-Style: Festive Food & Walking tour

star-5
15
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
$69.99
From
$69.99

Chicago Walking Tour: Modern Architecture

Chicago Walking Tour: Modern Architecture

star-5
15
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
$30.00
From
$30.00

Go City: Chicago Explorer Pass - Choose 2, 3, 4, 5, 6 or 7 Attractions

Go City: Chicago Explorer Pass - Choose 2, 3, 4, 5, 6 or 7 Attractions

star-4
218
The easiest and most affordable way to explore some of Chicago's top attractions at your own pace, the Chicago Explorer Pass by Go City saves you up to 40 percent off compared to buying individual attraction tickets. Create your own sightseeing itinerary by choosing 2, 3, 4, 5, 6 or 7 attractions, tours, and activities from among more than 25 top sites, including SkyDeck, 360 Chicago, the Field Museum, a shoreline sightseeing cruise, a hop-on hop-off Big Bus tour, Lincoln Park Zoo, Navy Pier, and LEGOLAND® Discovery Center. Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes are valid for two years from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for 60 days and/or the remaining number of attraction choices purchased.
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  • 60 days
From
$59.00
From
$59.00

Filters

What people are saying about Walking Tours in Chicago

star-5
Gangsters and Ghosts Tour in Chicago
"My tour guide was so friendly and she knows her history! I enjoy learning about the different topics she brought up! Awesome tour!"..."
star-5
Chicago Favorites Ultimate Food & Walking Tour
"Very interesting. We really enjoy it! It was very cold so just the right amount of time. My daughter and I were enjoying a few days away before she started a new job."..."
star-5
Chicago Architecture Walking Tour: Dazzling Interiors™ of the Loop
"Kylie was a knowledgeable, and energetic guide. As someone who does not know a lot about architecture, I came away having gained some knee knowledge and an appreciation it."..."
star-5
Underground Donut Tour: Chicago's First Donut Tour
"Other than eating donuts, we really didn't know what to expect. We ended up learning some interesting tidbits about Chicago along the way. Our guide Jackson was absolutely amazing!"..."
star-5
Chicago in a Day: Food, History and Architecture Combo Tour
"What an experience! Tony was our tour guide & he was fantastic! Food was awesome & he was super knowledgeable"..."
star-5
Chicago Architecture River Cruise
"The tour guide was so knowledgeable with a great sense of humor and even played the harmonica at the end. I learned so much about the historical skyline and the skyscrapers were absolutely beautiful."..."
star-5
90-Minute Chicago River Architecture Tour
"The view of buildings from the river was amazing!! The narration gave us so much information! We enjoyed it very much!"..."
star-5
Chicago Crime and Mob Bus Tour
"Katie was great fun and very informative! We had a great time and learned a lot of cool facts about the history Chicago."..."
star-5
Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour
"Thomas was a fantastic guide for an awesome tour around Chicago, food was tasty, he told some interesting stories, shoreline was gorgeous!"..."
star-5
45-Minute Chicago River Architecture Tour from Magnificent Mile
"The whole experience was great we had a good time. It was a very educational trip down the Chicago river."..."
star-5
Chicago Lake and River Architecture Tour
"Tour guide was very knowledgeable and gave good information. Experiencing the lock was very interesting."..."
star-5
Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals
"Excellent walk to view street art/ murals/ graffiti that I otherwise never would have observed or learned about. Recommend !"..."
star-5
Big Bus Chicago Hop-On Hop-Off Tour
"Very helpful as we had a walker to deal with and our drivers were wonderful. Looking forward to our next three theater tours San Francisco Los Angeles and San Diego."..."
star-5
Chicago Sunset Cruise
"The waves coming up over the side onto the boat’s windows!!! Very exciting ! Next time I will do this in the summer!"..."
star-5
Behind-the-Scenes Tour of Historic Chicago Theatre
"Tour guide was excellent and the Theatre is just amazing. From the history to the breathtaking details of its structure, it is a must see on your trip to Chicago!"..."
star-5
Chicago Craft Brewery Barrel Bus Tour
"Had an awesome time Ted was fantastic and the sing along at the end was perfect ending to a fun time."..."
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 Walking Tour: Art Deco Skyscrapers
"This tour was great. The leader Marian was very kind and knowledgeable . The Chicago architectural tour is a must. Thank you. I had a great time."..."
star-5
Chicago Loop Walking Tour
"I was the only person on the tour and Kevin was amazing! His knowledge and history of Chicago were excellent. He realized that I truly love the details and spent allot of time pointing them out. Super friendly, knowledgeable, highly recommend him for any city tour. You will not be disappointed!"..."
star-5
Holiday Hike Chicago-Style: Festive Food & Walking tour
"Our guide, Robert, was absolutely awesome. He was well organized, knowledgeable, and FUN! We had taken previous tours, and though we heard the same stories and theories...Robert's delivery of the information was detailed, to the point, and organized. The tour had great flow, and easily paced. Thanks again to Robert, for a memorable day 😀 👍"..."
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."..."
star-5
Go City: Chicago Explorer Pass - Choose 2, 3, 4, 5, 6 or 7 Attractions
"My grandson and I had an amazing quality time at the Willis tower and Navy Pier. Met wonderful people and the day lasted to enjoy all the rides and activities. A memorable time for sure !!!"..."

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?
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What Walking Tours in Chicago are taking additional safety precautions?
Q:
What Walking Tours in Chicago are good for avoiding crowds?