Chicago Walking & Biking Tours

Chicago Walking & Biking Tours

Walking & Biking Tours

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

5 star rating: Highly Recommended 54 Reviews

Get an in-depth look at Chicago Loop architecture on a walking tour that takes you inside landmark buildings in the design-rich city. Appreciate the interiors ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $26.00

Tastes of Chicago Bike Tour: Chicago-Style Pizza, Beer, Cupcakes and Hot Dogs

5 star rating: Highly Recommended 40 Reviews

Taste the flavors of Chicago, both edible and cultural, on a bike tour through the city. Sample four of Chicago’s favorite foods and drinks –pizza, ...  Read more

Location: Chicago, Illinois
Duration: 4 hours

From USD $79.50

Chicago Lakefront Neighborhoods Bicycle Tour

5 star rating: Highly Recommended 34 Reviews

See Chicago off the tourist beat on this guided bicycle tour. Your expert local guide will lead you to Chicago’s best quiet neighborhood streets, ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $51.45

Tastes of Chicago Walking Tour: Chicago-Style Pizza, Beer, Brownies and Italian Beef

5 star rating: Highly Recommended 31 Reviews

Experience Chicago on a walking and food tour of the central business district. Visits to legendary sites such as Palmer House Hotel, Marshall Field’s ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $59.00

Historic Chicago Walking Bar Tour

5 star rating: Highly Recommended 18 Reviews

Explore downtown Chicago on a pub crawl with an educational twist! Your expert guide shares entertaining facts about the history of jazz, theater, social ...  Read more

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $38.00

Chicago Pedway Walking Tour

4.5 star rating: Recommended 61 Reviews

Explore Chicago by following the heated tunnels, walkways, and passages that connect the city’s famous landmarks and buildings. Your comedic guide takes you ...  Read more

Location: Chicago, Illinois
Duration: 90 minutes

From USD $20.00

Chicago Holiday Stroll and Food Tour

5 star rating: Highly Recommended 3 Reviews

Experience the magic of the holidays, Chicago style, on a food and walking tour of the lively downtown. Your knowledgeable guide shares holiday traditions such ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $59.00

Chicago Chocolate Lover's Walking Tour

3 star rating: Worth doing 9 Reviews

Let your sweet tooth lead the way on this 2-hour chocolate walking tour in Chicago. As you walk along the Magnificent Mile with your local guide, visit ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $40.00

Chicago Walking Tour: Art Deco Skyscrapers

5 star rating: Highly Recommended 37 Reviews

Discover the opulent exteriors and interiors of the Roaring '20s Jazz Deco and the classic finishes of Art Moderne buildings in this 2 hour tour. Learn ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $18.00

Chicago Walking Tour: Historic Skyscrapers

5 star rating: Highly Recommended 32 Reviews

Perhaps Chicago's most identifiable claim to fame resides in its architecture. The prototype of the modern industrial metropolis arose from the ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $18.00

City Lights at Night Bicycle Tour

4 star rating: Recommended 2 Reviews

Bike through Chicago's most attractive locations at night and discover her charming neighborhoods. Enjoy a leisurely and informative biking ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $51.45

Chicago History and Riverwalk Tour

5 star rating: Highly Recommended 7 Reviews

On this fun and fascinating walking tour, learn about how Chicago grew from swampland bordering Lake Michigan into the thriving metropolis that it is today. ...  Read more

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $25.00

The World Within Walking Tour

5 star rating: Highly Recommended 4 Reviews

Explore some of the most stunning interior spaces you’ll ever see – spaces you’d surely pass by without a second glance if you weren’t ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $25.00

Walking and Food Tour: Chicago World's Fair of 1893

5 star rating: Highly Recommended 1 Review

Step back in time on a 3-hour walking tour of Chicago highlighting the food, drink and architecture of the 1893 World’s Fair. Stroll through the city’s ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $59.00

Naperville Food and Culture Walking Tour

Located just west of downtown Chicago, Naperville embodies Midwest friendliness and charm. Enjoy a cultural walking tour around its historic downtown, nosh on ...  Read more

Location: Naperville, Illinois
Duration: 3 hours

From USD $46.00

Chicago History Indoor Walking Tour

5 star rating: Highly Recommended 2 Reviews

Before it was the Chicago we know today — bold, diverse, thrilling and rich in culture — it was a marshy swampland bordering Lake Michigan. Much has changed ...  Read more

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $25.00

Chicago Walking Tour: Modern Architecture

5 star rating: Highly Recommended 8 Reviews

Explore Chicago's international, modern and postmodern movements, from the powerful, minimalist work of Mies van der Rohe's to contemporary styles ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $18.00

Chicago Independent Bike Tour with Full-Day Rental

5 star rating: Highly Recommended 1 Review

Explore Chicago at your own pace on an independent bike tour. With your full-day bike rental, pedal along Lake Michigan and visit top Chicago ...  Read more

Location: Chicago, Illinois
Duration: Flexible

From USD $20.55

Underground Donut Tour - Chicago's Only Donut Tour

Taste some of the finest donuts that Chicago has to offer on this 2 hour Walking Tour.  On this tour, we'll make four stops at some of the best donut spots in ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $30.00

Sweet Tooth Tour of Chicago

1 star rating: I do not recommend this 1 Review

Can’t decide which dessert you want to satisfy your sweet tooth? No need to pick and choose. Join us as we walk through Chicago, tasting a smorgasbord of ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $49.99

Cupcake Walking Tour in Chicago

5 star rating: Highly Recommended 2 Reviews

Satisfy your sweet tooth on this cupcake walking tour in Chicago, one of the birthplaces of the modern gourmet cupcake craze. Your local guide will ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $40.00

Open Your Eyes Walking Tour

5 star rating: Highly Recommended 2 Reviews

One of the benefits of researching and creating architecture walking tours is all of the fascinating discoveries one makes along the way – the hidden ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $25.00

Pedway Explorers Walking Tour

5 star rating: Highly Recommended 2 Reviews

Discover downtown Chicago from a different angle on this fascinating walking tour. The city’s Pedway system spans nearly five miles in length, and is ...  Read more

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $25.00

Telling the Story Walking Tour

5 star rating: Highly Recommended 2 Reviews

Explore Chicago by walking through the foundations of modern architecture itself, from the "Father of the Skyscraper" to Chicago's very own style.

Location: Chicago, Illinois
Duration: 2 hours

From USD $25.00

Chicago Riverwalk Walking Tour

4 star rating: Recommended 1 Review

The recently completed Chicago Riverwalk — a beautiful pedestrian walkway that follows the Chicago River as it flows through downtown — is one of the best ...  Read more

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $25.00
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