Chicago Walking Tours

Chicago Walking Tours

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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

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: Inside the Architecture of the Loop

5 star rating: Highly Recommended 30 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 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

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

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

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

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: 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

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

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

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

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

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

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

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

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

Creating the Melting Pot Walking Tour

Though all of Chicago’s neighborhoods are, of course, culturally rich, the West Loop is perhaps the closest and most accessible to visitors who would ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $25.00

Open Your Eyes Walking Tour

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

Rebuilding the Second City Walking Tour

River North, one of the oldest neighborhoods in Chicago, has experienced unparalleled evolution over the past 200 years – and Inside Chicago Walking ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $25.00

Beyond the Boat Walking Tour

5 star rating: Highly Recommended 1 Reviews

A boat tour is a great start to exploring Chicago, but we will take you way beyond anything you could ever experience from a boat.

Location: Chicago, Illinois
Duration: 2 hours

From USD $25.00

Pedway and Loop - History and Architecture Tour

Discover Chicago like no other walking tour in the city.  Listen to great stories about Chicago's history while exploring the secrets of the Pedway ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $20.00

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

The Original Taste of the Pedway Tour

5 star rating: Highly Recommended 1 Reviews

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
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