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76 Chicago Walking Tours

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Free Cancellation:Get a full refund up to 24 hours in advance on most experiences.See Details

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-4.5
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  
$27.00
From  
$27.00
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  • 2 hours
  • Free Cancellation

Chicago Prohibition Tour

Chicago Prohibition Tour

star-4.5
Visit four historic bars in operation since Prohibition in Chicago, and learn from a knowledgeable guide about the surreptitious world of the speakeasy. This adults-only tour takes you by coach to once-illicit establishments in Old Town, Wicker Park and the Chicago Loop where liquor, jazz and mobsters ruled. You’ll hear about Chicago gangsters like Al Capone and learn the historical context for the decade-long ban of alcohol. If you’d like, you can purchase recommended craft cocktails and signature drinks of the 1920s.
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  • 3 hours 30 minutes
  • Free Cancellation
From  
$45.00
From  
$45.00
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  • 3 hours 30 minutes
  • Free Cancellation

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

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

star-5
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  
$99.00
From  
$99.00
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  • 5 hours
  • Free Cancellation

Famous Tastes of Chicago Food Tour

Famous Tastes of Chicago Food Tour

star-4.5
Discover Chicago’s food, history, architecture and culture on this 3-hour, small-group walking tour. Try six of the Windy City’s quintessential staples from local restaurants and specialty food shops like Pizano’s Pizza and the Berghoff, the oldest family run-establishment in Chicago. Taste local favorites including deep-dish pizza,  Chicago Italian Beef Sandwich and chocolates from Fannie May, just to name a few. Along the way, see and learn about the historical, cultural and architectural components that make up this legendary town.
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  • 3 hours
From  
$63.07
From  
$63.07
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  • 3 hours

Go Chicago Explorer Pass with SkyDeck and 360 Chicago

Go Chicago Explorer Pass with SkyDeck and 360 Chicago

star-4.5
The easiest and most affordable way to explore some of Chicago's top attractions at your own pace, the Go Chicago Explorer Pass saves you up to 42 percent on regular ticket prices. Create your own sightseeing itinerary by choosing 3, 4, or 5 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.
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  • 30 days
From  
$66.00
From  
$66.00
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  • 30 days

Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour

Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour

star-5
Venture inside renowned Chicago landmarks, elegant lobbies, and underground corridors on this walking tour. Your expert guide will share insights about interior architectural features of this design-rich city—from mosaic domes to the sprawling Chicago Pedway System—bringing the details of the Windy City into vivid focus. Stop to admire Chase Tower, the Marshall Field and Company Building, the Chicago Cultural Center, and more.
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  • 2 hours
From  
$28.00
From  
$28.00
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  • 2 hours

iFLY Chicago-Lincoln Park Indoor Skydiving

iFLY Chicago-Lincoln Park Indoor Skydiving

star-5
Feel the rush of skydiving without going anywhere near a plane, with this indoor skydiving experience in Chicago. Start off with thorough training so you feel confident and know what to expect. Then, enjoy two 60-second ‘free fall’ experiences in a technologically advanced vertical wind tunnel, which feels much like real skydiving. No experience is necessary, and your instructor will give you hands-on assistance when you need.
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  • 1 hour 15 minutes
From  
$76.25
From  
$76.25
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  • 1 hour 15 minutes

Chicago Loop Secret Food Tour

Chicago Loop Secret Food Tour

star-5
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  
$77.70
From  
$77.70
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  • 3 hours

Best in Chow: Chicago River North Food Tour

Best in Chow: Chicago River North Food Tour

star-5
Go beyond deep-dish on this culinary walking tour of Chicago, which includes five tastings of classic Windy City cuisine. Navigate the endless options of downtown dining with a guide who can provide insight into the best food Chicago has to offer, and skip the lines and the wait with VIP access to popular restaurants.
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  • 150 to 180 minutes
  • Free Cancellation
From  
$60.00
From  
$60.00
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  • 150 to 180 minutes
  • Free Cancellation

Chicago Theatre Marquee Behind-the-Scenes Tour

Chicago Theatre Marquee Behind-the-Scenes Tour

star-4
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
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  • 1 hour
  • Free Cancellation

Holiday Hike Chicago-Style: Festive Food & Walking tour

Holiday Hike Chicago-Style: Festive Food & Walking tour

star-5
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  
$76.99
From  
$76.99
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  • 3 hours
  • Free Cancellation

Chicago Favorites Food and Walking Tour

Chicago Favorites Food and Walking Tour

star-5
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.
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  • 2 hours 30 minutes
From  
$59.99
From  
$59.99
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  • 2 hours 30 minutes

Discover Chicago's Underground City - all indoor walking tour

Discover Chicago's Underground City - all indoor walking tour

star-4.5
Discover a lesser-known side of the Windy City on this Chicago Pedway tour, a 1.5-hour walking excursion through the many heated passageways, tunnels, and corridors that link some of the town's most iconic buildings. Follow your humorous guide on an insider's exploration of these relatively unknown walkways, learning about the area's architecture and history as you go. It's a great way to explore a different side of Chicago unknown to most visitors.
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  • 1 hour 30 minutes
  • Free Cancellation
From  
$24.95
From  
$24.95
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  • 1 hour 30 minutes
  • Free Cancellation

Underground Donut Tour - Chicago's First Donut Tour

Underground Donut Tour - Chicago's First Donut Tour

star-5
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
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  • 2 hours
  • Free Cancellation

Historic Chicago Walking Bar Tour

Historic Chicago Walking Bar Tour

star-4.5
Explore downtown Chicago on a pub crawl with an educational twist! Your expert guide shares entertaining facts about the history of jazz, theater, social clubs, and the Prohibition era in the Windy City as you take in historic buildings and architecture. Use iPads to view historic photos and videos that accompany your guide’s stories as you stop in both famous and hidden bars for drinks and appetizers. A short walk allows plenty of time to see Chicago’s famous architecture and pubs on this tour – great for visitors and locals alike!
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  • 2 hours 30 minutes
From  
$38.00
From  
$38.00
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  • 2 hours 30 minutes

Chicago Style Food Tour

Chicago Style Food Tour

star-4.5
Discover Chicago’s food, history, architecture and culture on this small-group walking tour. Try the Windy City’s quintessential staples from local restaurants and specialty food shops like Downtown Dogs and the world-famous Billy Goat Tavern. Taste local favorites including deep-dish pizza, a Chicago-style hot dog, and chocolates from Fannie May, just to name a few. Along the way, see and learn about the historical, cultural, and architectural components that make up this legendary town.
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  • 3 hours
From  
$63.07
From  
$63.07
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  • 3 hours

Small-Group Chicago Food Tour: Chinatown

Small-Group Chicago Food Tour: Chinatown

star-5
Sample different styles and varieties of Chinese food during this 3-hour walking tour of Chicago's Chinatown. Follow your local food-loving guide through one of the oldest Chinese neighborhoods in the country to taste Mandarin-style, Hong Kong-style and Szechuan-style delicacies. The price of this small-group tour, limited to 12 people, includes tastings at 5 restaurants; enough food to add up to a full lunch.
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  • 3 hours
  • Free Cancellation
From  
$75.00
From  
$75.00
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  • 3 hours
  • Free Cancellation

Chicago Walking Tour: Art Deco Skyscrapers

Chicago Walking Tour: Art Deco Skyscrapers

star-4.5
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  
$28.60
From  
$28.60
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  • 1 hour 30 minutes
  • Free Cancellation

Sin and Suds Beer Tour in the Loop and South Loop

Sin and Suds Beer Tour in the Loop and South Loop

star-5
Explore Chicago’s Loop and South Loop neighborhoods — and get a taste of some local beverages — on this guided, 3-hour beer tour. Visit popular downtown establishments, sample some of the city’s finest brews and learn how beer goes with Chicago’s criminal past, discovering the basics of the Windy City’s vice history. From Al Capone and the local mob scene to the infamous Sands, the toughest criminal district in the city — this tour creates a unique experience that is both fun and memorable. Beer tastings plus a pizza pairing at one location included.
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  • 3 hours
  • Free Cancellation
From  
$73.70
From  
$73.70
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  • 3 hours
  • Free Cancellation

Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

star-5
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  
$30.00
From  
$30.00
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  • 2 hours
  • Free Cancellation

Magnificent Mile Photo Shoot and Walking Tour

Magnificent Mile Photo Shoot and Walking Tour

Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, let us be your personal paparazzi. You will be escorted by a local professional photographer who will guide you through the pre-planned route and will take pictures of your experience so you can return home with photos you will be proud to share with your family and friends.Your photo tour includes:-1 or 2-hour private session with a professional, local photographer-High-resolution edited images delivered via a private online gallery within 24-48 hours--1-hour session includes 10 digital images--2-hour session includes 20 digital images-Edited images delivered to your email within 24-48 hours from your tour*Additional photos and prints can be purchased through your online gallery.
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  • 1 to 2 hours
  • Free Cancellation
From  
$150.00
From  
$150.00
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  • 1 to 2 hours
  • Free Cancellation

Millennium Park Photo Shoot and Walking Tour

Millennium Park Photo Shoot and Walking Tour

star-5
On this two-in-one tour, you won’t just discover Chicago’s highlight public park: you’ll also do so in the company of a professional photographer, who will capture portrait shots as you explore. Pick from multiple daily tour times, and meet your private guide at Millennium Park. You can look forward to seeing park highlights like Anish Kapoor’s "Cloud Gate" sculpture (better known as “The Bean”), Lurie Garden, Maggie Daley Park, Buckingham Fountain, and more. Following the tour, receive high-quality digital photos of your experience.
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  • 1 to 2 hours
  • Free Cancellation
From  
$150.00
From  
$150.00
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  • 1 to 2 hours
  • Free Cancellation

Crime and Haunted Tour in Chicago

SPECIAL OFFER

Crime and Haunted Tour in Chicago

star-5
Haunted places and gangster hangouts, hidden history and crime scenes. Walking tour with a Secret route, we take you where no one else can. This isn’t just another boring tour — it is an adventure where you travel back in time as a gangster member. Prohibition Era, Speakeasies, Death Alley and Congress hotel part of our route. You will hear untold stories and outlandish details. Come discover the hidden.
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  • 1 hour 45 minutes
  • Free Cancellation
From  
$25.81
$29.00
$3.19 savings
From  
$25.81
$29.00
$3.19 savings
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  • 1 hour 45 minutes
  • Free Cancellation

Best of Chicago: History & Culture Tour with Chocolate and Popcorn

Best of Chicago: History & Culture Tour with Chocolate and Popcorn

star-5
The Windy City is known for its spectacular architecture and eclectic food scene. Experience both on this tour through the downtown that combines sights with nibbles. Take in famous landmarks like the Wrigley Building, Tribune Tower, and Cloud Gate on foot and with the scenic L train or water taxi along the Chicago River. Taste popcorn and chocolate from two beloved city eateries during the tour.
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  • 2 hours 30 minutes
  • Free Cancellation
From  
$49.00
From  
$49.00
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  • 2 hours 30 minutes
  • Free Cancellation


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