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Top Chicago Walking & Biking Tours

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

Chicago dogs, deep-dish pizza, cupcakes and craft beer are all sampled on this 4-hour bike tour through the windy city. You’ll cover about 13 miles (21 km), following an informative guide at a moderate pace through the Chicago neighborhoods of Wrigleyville, the Gold Coast, Old Town, Lakeview and Lincoln Park. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
$77.99 USD
From  
$77.99 USD
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Chicago Favorites Food and Walking Tour

Stroll through downtown Chicago on this 2.5-hour food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, brownies, and local beer. All tastings and beverages are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels.
  • Duration: 2 hours 30 minutes
  • Free Cancellation
  • Duration: 2 hours 30 minutes
  • Free Cancellation
$59.00 USD
$3.01 USD savings
From  
$55.99 USD
$59.00 USD$3.01 USD savings
$59.00 USD
$3.01 USD savings
From  
$55.99 USD
$59.00 USD$3.01 USD savingsSee Details

Chicago Prohibition Tour

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.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
$45.00 USD
From  
$45.00 USD
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Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour

Venture inside renowned Chicago landmarks, elegant lobbies, and underground corridors on this 2-hour 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.
  • Duration: 2 hours
  • Duration: 2 hours
From  
$28.00 USD
From  
$28.00 USD
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Chicago's Greatest Hits Bicycle Tour

Explore Chicago’s most iconic sites with a 2.5-hour bike tour that explores Museum Campus, parks and monuments. Follow your guide along the waterfront as you soak up the city skyline and enjoy the breeze along the easy going route. Circle the Buckingham Fountain while you learn the history of the city’s public art, parks and museums, and capture unforgettable images of the Windy City.
  • Duration: 2 hours 30 minutes
  • Free Cancellation
  • Duration: 2 hours 30 minutes
  • Free Cancellation
From  
$48.99 USD
From  
$48.99 USD
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Underground Donut Tour - Chicago's First Donut Tour

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 gluten- and nut-free options are also available.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$30.00 USD
From  
$30.00 USD
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Famous Tastes of Chicago Food Tour

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.
  • Duration: 3 hours
  • Duration: 3 hours
From  
$63.50 USD
From  
$63.50 USD
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Discover Chicago's Underground City on the all-indoor Pedway Tour

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.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
$23.00 USD
From  
$23.00 USD
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Historic Chicago Walking Bar Tour

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!
  • Duration: 2 hours 30 minutes
  • Duration: 2 hours 30 minutes
From  
$38.00 USD
From  
$38.00 USD
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Holiday Hike: Festive Chicago Food and Walking Tour

Stroll through Chicago's winter streets, lit up for the holidays, on this 3-hour walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows at Macy's, and ice skating at Millennium Park. Follow your local guide on a walk down festively decorated State Street and sample generous tastes of classic Chicago foods and holiday treats. Seasonal craft beer tastings will help you stay warm and toasty; please note this tour operates in all weather conditions, so dress appropriately.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$80.00 USD
From  
$80.00 USD
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Chicago's Chinatown Food and Walking Tour

Explore Chicago's Chinese food scene on this walking tour in the Chinatown district. With a guide, learn about the cuisine of different regions of China and how Chinese culture has influenced Chicago and other areas. You'll enjoy included tastings from restaurants and other food venues in Chinatown—a great way to start a night out in the city.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$59.99 USD
From  
$59.99 USD
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2.5-Hour Cupcake Tour Of Chicago

Visit the best dessert boutiques along the Magnificent Mile in Chicago on a 2.5-hour cupcake tour led by a guide. Skip-the-line access and all cupcakes are included as you visit up to five bakeries. You'll also see landmarks like the Wrigley Building, Water Tower Place, John Hancock Center, and the Chicago River, and hear commentary about Chicago from your guide.
  • Duration: 2 hours 30 minutes
  • Free Cancellation
  • Duration: 2 hours 30 minutes
  • Free Cancellation
From  
$50.00 USD
From  
$50.00 USD
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Chicago Walking Tour: Art Deco Skyscrapers

Admire the incredible façades and intricate interiors of the Windy City's 1920s art deco and art moderne buildings during this 2-hour 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.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
$26.00 USD
From  
$26.00 USD
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Chicago Bike Tour

Experience the top sights of the Windy City on a 3.5-hour guided bike tour. Traveling on two wheels allows you to skip the sluggish pace of city traffic and avoid the limitations of walking. Let your guide take care of narration and navigation as you ride through eight neighborhoods, including Lincoln Park and Old Town. Stop for photos as you pedal onwards to the city’s lakefront and beyond.
  • Duration: 210 to 240 minutes
  • Free Cancellation
  • Duration: 210 to 240 minutes
  • Free Cancellation
From  
$42.51 USD
From  
$42.51 USD
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Chicago Style Food Tour

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 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.
  • Duration: 3 hours
  • Duration: 3 hours
From  
$63.50 USD
From  
$63.50 USD
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Chicago World's Fair of 1893 Walking Tour

Discover the lasting influence of the 1893 World’s Fair in Chicago on a 3-hour walking and food tour of downtown. See the historic Auditorium Building, the Chicago Athletic Association Hotel and other examples of Chicago’s fine architecture. You’ll also sample fresh–brewed beers and some tasty German fare among other refreshments, with enough food for a light meal. Your guide provides informative commentary and entertaining games during your Chicago walking tour, which mostly takes place indoors, making it ideal for all seasons.
  • Duration: 2 hours 45 minutes
  • Duration: 2 hours 45 minutes
From  
$42.00 USD
From  
$42.00 USD
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Small-Group Chicago Food Tour: Chinatown

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.
  • Duration: 3 hours 25 minutes
  • Free Cancellation
  • Duration: 3 hours 25 minutes
  • Free Cancellation
From  
$60.00 USD
From  
$60.00 USD
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NEW TO VIATOR

Chicago Theatre Marquee Tour Tickets

Go on a history-filled journey, from the inception of this majestic venue in 1921, all the way to its present-day incarnation as a premiere entertainment venue. The Marquee Tour encompasses historical and architectural highlights of the building, including the grand lobby, sweeping staircase and majestic auditorium. Tour guests have the chance to stand on the famous Chicago Theatre stage, plus view artist signatures on the dressing room walls, including Frank Sinatra, Dean Martin, Dolly Parton and so many more!**Please note, some areas of the theatre may be restricted based on performance schedules.
  • Duration: 1 hour
  • Free Cancellation
  • Duration: 1 hour
  • Free Cancellation
From  
$18.00 USD
From  
$18.00 USD
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Best in Chow: Chicago River North Food Tour

Go beyond deep-dish on this 3-hour 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.
  • Duration: 150 to 180 minutes
  • Free Cancellation
  • Duration: 150 to 180 minutes
  • Free Cancellation
From  
$60.00 USD
From  
$60.00 USD
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NEW TO VIATOR

Chicago City Skydeck Experience - Out On The Awesome Ledge!

Willis Tower can be seen from around the Windy City and is a highlight of most sightseeing tours and Chicago River cruises. For a unique Chicago dining experience, book lunch or dinner at Willis Tower, where you can enjoy a Chicago speciality, deep-dish pizza on either the 99th floor or on the Skydeck. Book as an Early riser with us and enjoy an early-access breakfast experience before the Skydeck opens to the public.
  • Duration: 1 to 2 hours
  • Free Cancellation
  • Duration: 1 to 2 hours
  • Free Cancellation
From  
$32.00 USD
From  
$32.00 USD
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Old Polonia and Wicker Park History and Food Tour

Explore the past and present of two Chicago neighborhoods on this guided, 2.5-hour walking tour. Visit Wicker Park, once infamous as a home for gang bangers, drug addicts and prostitutes, it’s now widely considered one of the trendiest neighborhoods in America. Then walk through the West Town district of Noble Square, formerly known as ‘Old Polonia.’ Along the way, see many popular points of interest and enjoy food tastings at some of the area’s best eateries.
  • Duration: 2 hours 30 minutes
  • Duration: 2 hours 30 minutes
From  
$52.00 USD
From  
$52.00 USD
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CHICAGO UNDERGROUND PEDWAY TOUR WITH FOOD, CHOCOLATE & WINE

Discover the sights and flavors of Chicago on a 1.5- to 2-hour tour via the underground Pedway. The subterranean tour is the perfect way to explore the city without exposing yourself to the elements. Follow your guide to Macy's, the Thompson Center, City Hall, and more. Along the way, whet your appetite with Garrett Mix popcorn, artisan sandwiches, and frozen kefir. The 4pm tour on Friday also includes a wine tasting.
  • Duration: 90 to 120 minutes
  • Free Cancellation
  • Duration: 90 to 120 minutes
  • Free Cancellation
From  
$50.00 USD
From  
$50.00 USD
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CHICAGO ARCHITECTURE TOUR

Chicago is the undisputed Architectural capital of the world. Take an educational journey through downtown Chicago with an expert tour guide. Visit some of Chicago's most significant contributions to the Architecture world as well as some little known gems.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$25.00 USD
From  
$25.00 USD
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Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

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.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$30.00 USD
From  
$30.00 USD
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(888) 651-9785
(888) 651-9785