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Top Chicago Walking & Biking Tours

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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
From
US$28,00
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  • Duration: 2 hours
From
US$28,00

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
From
US$30,00
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  • Duration: 2 hours
  • Free Cancellation
From
US$30,00

SPECIAL OFFER

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
From
US$74,34
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  • Duration: 3 hours
  • Free Cancellation
From
US$74,34

SPECIAL OFFER

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
From
US$61,50
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  • Duration: 2 hours 30 minutes
  • Free Cancellation
From
US$61,50

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
From
US$23,00
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  • Duration: 1 hour 30 minutes
  • Free Cancellation
From
US$23,00

SPECIAL OFFER

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
From
US$26,00
US$29,00  US$3,00 savings
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  • Duration: 1 hour 30 minutes
  • Free Cancellation
From
US$26,00
US$29,00  US$3,00 savings

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
From
US$30,00
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  • Duration: 2 hours
  • Free Cancellation
From
US$30,00

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
From
US$38,00
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  • Duration: 2 hours 30 minutes
From
US$38,00

Chicago Architecture Walking Tour: High-Up and Low-Down Views of the City

Get great views of Chicago on a walking tour that has special access to buildings not open to the general public. Your guide leads you to places with fantastic perspectives of the Windy City, and gives you time for photo ops throughout the 2-hour tour. Hear insightful commentary about the city as you cover about 1.5 miles on foot, walking at a leisurely pace with frequent stops.
  • Duration: 2 to 2.5 hrs
  • Free Cancellation
From
US$30,00
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  • Duration: 2 to 2.5 hrs
  • Free Cancellation
From
US$30,00

Chicago Loop Walking Tour

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.
  • Duration: 2 hours
  • Free Cancellation
From
US$30,00
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  • Duration: 2 hours
  • Free Cancellation
From
US$30,00

Chicago Winter Holiday Walking Tour With Drinks

Celebrate the holidays in Chicago on a special 2.5-hour walking tour that serves up the Windy City's history with drinks and festive decorations. Wear your warm winter clothing for a tour that spends half the time indoors at landmark spots like the Marshall Field’s Department Store in addition to some time outdoors. Your guide shares commentary about the Daley family and Chicago's mayors, Christmas traditions in the city, and other Chicago lore as you stroll through downtown and pop into two establishments for drinks (optional and at own expense).
  • Duration: 3 hours
From
US$34,00
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  • Duration: 3 hours
From
US$34,00

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Chicago Walking Tour: Modern Architecture

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.
  • Duration: 1 hour 45 minutes
  • Free Cancellation
From
US$26,00
US$29,00  US$3,00 savings
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  • Duration: 1 hour 45 minutes
  • Free Cancellation
From
US$26,00
US$29,00  US$3,00 savings

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
From
US$57,00
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  • Duration: 3 hours
  • Free Cancellation
From
US$57,00

SPECIAL OFFER

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: 2 hours 30 minutes
  • Free Cancellation
From
US$58,27
US$64,75  US$6,48 savings
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  • Duration: 2 hours 30 minutes
  • Free Cancellation
From
US$58,27
US$64,75  US$6,48 savings

3-Hour Walking Tour: Chicago World's Fair of 1893

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: 3 hours
From
US$42,00
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  • Duration: 3 hours
From
US$42,00

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
From
US$59,00
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  • Duration: 3 hours
  • Free Cancellation
From
US$59,00

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
From
US$42,50
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  • Duration: 3 hours
  • Free Cancellation
From
US$42,50

SPECIAL OFFER

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
From
US$47,50
US$50,00  US$2,50 savings
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  • Duration: 2 hours
  • Free Cancellation
From
US$47,50
US$50,00  US$2,50 savings

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
From
US$42,51
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  • Duration: 3.5 to 4 hrs
  • Free Cancellation
From
US$42,51

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
  • Free Cancellation
From
US$42,08
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  • Duration: 2 hours
  • Free Cancellation
From
US$42,08

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
From
US$52,00
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  • Duration: 2 hours 30 minutes
From
US$52,00

Chicago Bike Tour and Skydeck Admission

Enjoy two Chicago experiences at one price with this combo bike tour and admission to the Skydeck Chicago at Willis Tower. With a guide, you'll ride through eight neighborhoods and along the Lake Michigan waterfront to take in the city's attractions and scenery, listening to stories and history about Chicago as you go. Then visit the Skydeck for a 360-degree view from 1,353 feet (412 meters) in the air.
  • Duration: 3.5 to 4 hrs
  • Free Cancellation
From
US$64,31
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  • Duration: 3.5 to 4 hrs
  • Free Cancellation
From
US$64,31

Walking Tour of Lincoln Park in Chicago

Step off the tourists’ path to visit Lincoln Park, a neighborhood beloved by Chicagoans for its stately homes, historic zoo, and stunning green areas. Your tour begins at the charming Children’s Fountain and continues to unexpected sites like the shrine of the first American saint. As your local guide leads you through the city’s largest park, you’ll marvel at the wild feel of this neighborhood just north of downtown Chicago.
  • Duration: 2 hours
  • Free Cancellation
From
US$30,00
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  • Duration: 2 hours
  • Free Cancellation
From
US$30,00

Chicago River Walking Tour

A river runs through it: the Chicago River passes right through the heart of downtown and is a major part of city identity. You’ll begin this walking tour at Navy Pier and follow your local guide along the scenic river walk. You’ll learn the role of the river in Chicago’s history, and stop to admire iconic architecture and bridges celebrated as feats of engineering.
  • Duration: 2 hours
  • Free Cancellation
From
US$30,00
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  • Duration: 2 hours
  • Free Cancellation
From
US$30,00


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