Chicago Walking Tours

Chicago Walking Tours

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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

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

5 star rating: Highly Recommended 25 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 Walking Tour: Inside the Architecture of the Loop

5 star rating: Highly Recommended 35 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

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

Chicago Walking Tour: Historic Skyscrapers

5 star rating: Highly Recommended 22 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

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

Chicago Walking Tour: Art Deco Skyscrapers

5 star rating: Highly Recommended 34 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

1893 Worlds Fair Tour with Bars and Food

5 star rating: Highly Recommended 1 Reviews

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 56 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 Pizza Walking Tour

5 star rating: Highly Recommended 5 Reviews

Taste some of Chicago’s finest deep-dish pizzas during a 2-hour walking tour to three top pizzerias. Start at the restaurant that created the famous pie, ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $45.00
$50.00 Save $5.00

Chicago Gangster Tour

1 star rating: I do not recommend this 2 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

Chicago History Tour Plus - River Walk

5 star rating: Highly Recommended 1 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 $25.00

The World Within Walking Tour

5 star rating: Highly Recommended 2 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 Tour of Old Polonia and Wicker Park with Food

5 star rating: Highly Recommended 1 Reviews

We will explore the past and present of the people, architecture, and foods of these vibrant and changing neighborhoods of Noble Square and Wicker Park.

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $45.00

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

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

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

River Walk Explorers Tour Plus

The River Walk will soon span from Lake Shore Drive to Lake Street and offer wonderful lush green spaces, cafes, retail establishments and numerous places to ...  Read more

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $25.00

The In The Loop Tour of Chicago

2 star rating: It was OK, but could have been better 1 Reviews

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: 90 minutes

From USD $20.00

Drunk History Tour of Chicago

Imbibe your way down the Windy City's Magnificent Mile on this innovative, interactive and slightly drunk tour complete with historical re-enactments, trivia ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $50.00

Open Your Eyes Walking Tour

5 star rating: Highly Recommended 1 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 Tour

5 star rating: Highly Recommended 2 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 Power Hour Tour

Come discover the history behind Millennium Park, the world's largest "green roof," and get an up-close experience of the art and stunning views that ...  Read more

Location: Chicago, Illinois
Duration: 60 minutes

From USD $15.00

Intro to Hyde Park

Walk through the historic Hyde Park neighborhood with a local guide to point out various points of interest.

Location: Chicago, Illinois
Duration: Flexible

From USD $20.00
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