Top Chicago Walking Tours

Taste some of Chicago's most iconic foods while walking through one of the Prohibition Era’s most fashionable and notorious neighborhoods. Learn about Chicago's world-famous cuisine...

On our 3 hour food walking tour of Chicago, you will taste delectable foods from 5 different delicious places. Tease your tastebuds as you savor...

Chicago is home to some of the world’s earliest skyscrapers. Get an up-close look at these 19th Century marvels, learn about innovations used to build...

Chicago’s Loop is home to some of the city’s most perfectly preserved Art Deco architecture designed during the Roaring 20s. See 7 stunning Art Deco...

Nightly Spirits’ Haunts and Hooligans Tour will illustrate Chicago’s haunted history of secret parlors, underground tunnels, murderous movie theaters and supernatural speakeasies. Whether you’re a...

Looking for iconic Mid-Century Modern architecture? What better place than Chicago with its triumvirate of modern architects (Mies van der Rohe, Bertrand Goldberg and SOM)...

Our private walking tour of the Chicago History Museum offers a personalized, in-depth experience led by expert guides who bring Chicago’s vibrant past to life...

Cover three Lincoln Park stops on a private walking tour through Chicago: the Peggy Notebaert Nature Museum, Lincoln Park Conservatory, and Lincoln Park Zoo. At...

We are Chicago's only paranormal investigation tour, and Chicago's oldest ghost and hauntings tours, founded by Ursula Bielski, Chicago's 35 year paranormal researcher and investigator....

Discover how a dirt road known as Pine Street transformed into a "Paris on the Prairie" and later into the Magnificent Mile, the city’s premier...

This lively overview of Chicago architecture explores iconic buildings from the 1890s to present. We'll compare and contrast a wide range of buildings with varying...

Ready to explore Chicago like never before? Whether you have just a couple of hours or a full day, my personalized city tours offer a...

Learn about the life and work of Louis Comfort Tiffany as we visit some of Chicago’s most magnificent art-glass and mosaic installations, each designed and...

We’ll begin our photo walk in Millennium Park with portraits at Cloud Gate (The Bean), one of Chicago’s most iconic landmarks. During our time together,...

Immerse yourself in the fascinating history of how a muddy Midwestern outpost transformed into the global capital of architecture. Experience everything from early, classically inspired...

Discover the amazing history and architecture of Chicago with expert tour guide Dave Lineal. Walk among gigantic towers of downtown and learn how Chicago became...

A 60-75-minute guided, behind-the-scenes exploration of the historic Chicago Theatre, one of the city’s most iconic landmarks. Stand on the famed Chicago theatre stage and...

Explore Chicago’s amazing architecture from the unique perspective of elevated trains and station platforms. Learn the history behind the famous "L" system and hear how...

Much of the historical information shared on this tour is unknown to most attendees. This tour also shows everything from the gritty to the pretty,...

There’s nothing more magical than downtown Chicago during the holidays. Bobby’s Bike Hike & Food Tours—internationally recognized for quality—presents the Holiday Hike, a 3-hour guided...