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Top Illinois Walking & Biking Tours

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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
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$55.00
From  
US$55.00
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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  
US$28.00
From  
US$28.00
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Underground Donut Tour - Chicago's First Donut Tour

Sample some of the Windy City’s tastiest donuts on this 2-hour Underground Donut Tour, celebrating the magic of Chicago’s tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit four 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  
US$30.00
From  
US$30.00
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Chicago Pedway Walking 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  
US$23.00
From  
US$23.00
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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
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$55.00
From  
US$55.00
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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
From  
US$76.83
From  
US$76.83
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Chicago Lakefront Neighborhoods Bicycle Tour

Pedal past the lakefront neighborhoods of Chicago's North Side on this 3-hour bike tour of the Windy City. Follow a local guide along quiet streets, city parks and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. Catch a glimpse of the Playboy Mansion, Oprah’s penthouse and the Victorian houses of Old Town. Select from several departure times in the morning or afternoon.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$63.67
From  
US$63.67
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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  
US$38.00
From  
US$38.00
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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  
US$26.00
From  
US$26.00
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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  
US$97.00
From  
US$97.00
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Chicago's Chinatown Food and Walking Tour

Explore Chicago's Chinese food scene on this 3-hour 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  
US$74.00
From  
US$74.00
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Chicago Crime and Pizza Walk

Explore the River North and Gold Coast neighborhoods in Chicago during a 2-hour walking that focuses on the city's famous deep-dish pizza and most notorious criminals.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
US$50.00
US$2.50 savings
From  
US$47.50
US$50.00US$2.50 savings
US$50.00
US$2.50 savings
From  
US$47.50
US$50.00US$2.50 savingsSee Details

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  
US$30.00
From  
US$30.00
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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  
US$52.00
From  
US$52.00
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Haunted Chicago Ghost and Pub Walking Tour

Enjoy a memorable Chicago experience with this haunted pub tour. Your costumed guide, dresses as a Flapper or 1920s Gangster, will lead you on a mile-long, 2.5-hour journey while telling spooky stories of forgotten cemeteries, lingering spirits, and more. Stop at three different bars for drinks (at own expense) as you learn the secret tales behind Chicago’s haunted past.
  • Duration: 2 hours 30 minutes
  • Free Cancellation
  • Duration: 2 hours 30 minutes
  • Free Cancellation
From  
US$25.00
From  
US$25.00
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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  
US$50.00
From  
US$50.00
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Chicago's Electric Bikes at Night Tour

See Chicago light up at night with a 3-hour bicycle tour of the Windy City’s most iconic sights and neighborhoods. Follow your guide along a leisurely route, watch the Buckingham Fountain light show and take in evening views of Millennium Park and the Museum Campus. Pedal through downtown streets, capture unforgettable images of Chicago’s magnificent skyline then finish your tour in the heart of the city.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$76.83
From  
US$76.83
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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  
US$80.00
From  
US$80.00
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Chicago Lincoln Park Bike Adventure

Experience Chicago like never before on this guided, 3-hour bicycle tour. Ride the walking- and cycling-only Chicago Lakefront Trail to and through the city’s beautiful beaches, parks and lagoons. See the coast of Lake Michigan and the breathtaking Chicago skyline, plus bustling Navy Pier, popular North Avenue Beach, the 35-acre Lincoln Park Zoo and Conservatory and much more. The use of a bike and helmet is included.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$42.50
From  
US$42.50
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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  
US$42.00
From  
US$42.00
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Bikes, Bites, and Brews: Chicago's West Side Foodie Ride

Taste food from around the world on this 4-hour cycling tour of Chicago. Follow your biking guide through the Chicago streets, stopping for views of Chicago’s famous architecture as well as bites like Mexican tortas, French sweets, and Polish pierogis.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
US$97.00
From  
US$97.00
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Chocolate Tour Of Chicago

Take a walk on the sweeter side of Chicago with a chocolate walking tour. Visit some of the city’s favorite chocolatiers. Learn about the history of the treat and see how Chicago businesses are crafting it in lots of delicious ways. And you bet, there will be samples.
  • Duration: 2 hours 30 minutes
  • Free Cancellation
  • Duration: 2 hours 30 minutes
  • Free Cancellation
From  
US$50.00
From  
US$50.00
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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: 3.5 to 4 hrs
  • Free Cancellation
  • Duration: 3.5 to 4 hrs
  • Free Cancellation
From  
US$42.51
From  
US$42.51
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Tike Hike: Chicago Family Bike Tour

Cruise through Chicago on this family-friendly bicycle tour catered to kids. Perfect for kids age 10 and under, this tour mixes fun games and contests in with educational stops at some of Chicago's iconic sights. Parents can ride along with their children on cruiser-style bikes during this safe, enjoyable 2-hour tour that covers an easy 4.5 miles (7 km).
  • Duration: 2 hours 30 minutes
  • Free Cancellation
  • Duration: 2 hours 30 minutes
  • Free Cancellation
From  
US$54.34
From  
US$54.34
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