Chicago Walking & Biking Tours

Chicago Walking & Biking Tours

Walking & Biking Tours

Only Show: Bike & Mountain Bike Tours | Walking Tours

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

5 star rating: Highly Recommended 32 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 $78.95

Chicago Chocolate Lover's Walking Tour

4 star rating: Recommended 7 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: Inside the Architecture of the Loop

5 star rating: Highly Recommended 29 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 ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $26.00

Tastes of Chicago Walking Tour: Chicago-Style Pizza, Beer, Brownies and Hot Dogs

5 star rating: Highly Recommended 24 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 $55.35

Chicago Lakefront Neighborhoods Bicycle Tour

5 star rating: Highly Recommended 23 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 $48.10

Chicago Walking Tour: Historic Skyscrapers

5 star rating: Highly Recommended 20 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
$23.00 Save $5.00

Cupcake Walking Tour in Chicago

5 star rating: Highly Recommended 1 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

Historic Chicago Walking Bar Tour

4.5 star rating: Recommended 14 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 $36.00

1893 Worlds Fair Tour with Bars and Food

A combination of food and drink with incredible architecture, fascinating historical stories of turn-of-the-century Chicago, and visual scavenger hunts and ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $55.00

Chicago Pedway Walking Tour

4.5 star rating: Recommended 55 Reviews

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

Location: Chicago, Illinois
Duration: 90 minutes

From USD $20.00

Chicago Walking Tour: Art Deco Skyscrapers

5 star rating: Highly Recommended 31 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
$23.00 Save $5.00

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 $48.10

Chicago History Indoor Walking Tour

5 star rating: Highly Recommended 2 Reviews

Learn the true "story" of Chicago's history and its amazing account of how a swampland located at the intersection of a lazy prairie river and Lake ...  Read more

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $20.00

Chicago Gangster Tour

1 star rating: I do not recommend this 1 Reviews

Chicago has a long history of organized crime and was famously home to the American mafia figure Al Capone. In 1850, Chicago had a population of 80,000 ...  Read more

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $35.00

Chicago Walking Tour: Modern Architecture

5 star rating: Highly Recommended 7 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
$23.00 Save $5.00

Pedway Brunch Tour

Explore the Pedway, hear great stories about Chicago and savor a delicious breakfast buffet all rolled into one on this unique walking tour.  Similar to ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $50.00

The World Within Walking Tour

5 star rating: Highly Recommended 1 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

Pedway Explorers Tour

5 star rating: Highly Recommended 1 Reviews

Discover the hidden secrets behind Chicago's secret weapon used to combat the city's cruel winters.  Learn to navigate the winding passages of one of the ...  Read more

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $20.00

Chicago Lincoln Park Bike Adventure

Enjoy the car-free lakefront trail and explore Chicago’s beaches, parks, lagoons, and gorgeous Lincoln Park Zoo (free admission). This tour offers a diverse ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $40.00

The Original Taste of the Pedway Tour

Celebrate the five senses of sight, sound, touch, smell and on this indoor walking tour we emphasize perhaps the best sense of all, taste! While inspecting the ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $50.00

The In The Loop Tour of Chicago

The “In The Loop” Tour is everything you want to know about Chicago all rolled into one fabulous walking tour. It’s architecture! History! ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $25.00

River Walk Brunch Tour

Join us on our highly acclaimed weekend Brunch Tour that features a little of everything; history, architecture, spectacular views, great storytelling and of ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $50.00

Telling the Story Walking Tour

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

River Walk and Loop - History and Architecture Tour

Our “River Walk & Loop History/Architectural Tour" is exactly as the name implies; the finest of everything that Chicago has to offer all ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $25.00

Chicago History Tour Plus - River Walk

Learn the true "story" of Chicago's history and its amazing account of how a swampland located at the intersection of a lazy prairie river and Lake ...  Read more

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $25.00
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