The 10 Best Walking Tours in Chicago

In recent years, Chicago neighborhoods have expanded their identity through bold street art adorning brick walls. Don’t make the same mistake as the average passerby by overlooking some of the best murals and paintings in Logan Square and Wicker Park – both of which have many restaurants, coffee shops, bars and book stores worth exploring before or after your tour. Offbeat Street Art Tour – Urban Graffiti, Art, and Mural Tour costs only $25 and takes place on Saturdays and Sundays.

Chicago’s eclectic architecture could consume an entire trip to Chicago. A good primer is Chicago Architecture Center’s Historic Treasures of Chicago tour, which unravels the mystery of Chicago’s ‘urban safari.’ Through the city’s early architectural achievements, you’ll get an idea of how Chicago has influenced the world. Set off for Michigan Avenue to get an art-deco thrill for around $25. Admission to the Chicago Architecture Center is included.

Inside Chicago prides itself on its ability to uncover the hidden secrets inside some of downtown Chicago’s most famous skyscrapers. The World Within: Inside the Dazzling Interiors of the Loop highlights the concrete structures reaching for the sky along with their intricate insides: Art Deco lobbies from the ’20s, glass mosaics and more. The price of the tour is $30 and takes place every day of the week but Tuesday and Wednesday.

Chicago After Dark emphasizes how beautiful the city is after dark, taking tour groups to secret gardens and outside music venues along the Chicago River and Lake Michigan. The night ends with Navy Pier’s weekly fireworks tour. This ‘architectural lite’ tour is ideal for those who want to learn but have shorter attention spans.

This Chinatown Culinary walking tour paints a picture of Chicago’s Chinese culture through the exploration off the beaten path. Gorge on authentic cuisine from the Canton, Mandarin and Szechuan regions of China with a traditional lunch included and explore the history of Chinese culture and food in Chicago. End your tour at an authentic tea house and try the special blends.

Chicago for Chicagoans Walking Tours will help you decipher some of the mystery behind the City of Neighborhoods. Many of their tours are limited and run by guides with the first-hand experience with the areas in question. The Pilsen Walking highlights the history and changes of one of Chicago’s most robust Latino neighborhoods and includes a discussion with a resident who’s part of a grassroots effort to preserve local culture. Tours take place Saturday and Sunday and work on a ‘pay-what-you-can’ structure. Suggested tips for guides is between $10 and $20.

Get your spook on with Chicago Hauntings, a tour company that’s been in the ghost business for 15 years. Thousands of unmarked graves compose the landscape of their Lincoln Park Ghost Walk – can you think of a better locale? See if you can spot ghosts from the Great Chicago Fire and learn about mob history by exploring the scene of the St. Valentine’s Day Massacre. Tours take place Monday through Thursday, along with Sunday. Tickets cost $28 for adults.

The Chicago Architecture Center is devoted to both the old and the new. Learn how to parse the differences between Chicago’s many architectural styles through the Chicago Icons: Connecting the Past and Present tour, or focus on the architecture that helped define design aesthetics around the world on the Chicago Modern tour.

Pizza is more than a carb in Chicago, it’s a legacy. Legend has it that deep-dish pizza was invented at Pizzeria Uno in Chicago back in 1943. NYC might think they have Chi-town beat, but you can settle that debate once and for all by tasting your way through up to 10 prominent pizzarias on this tour, which has been in operation for nearly a decade. Go classic with the famous burnt cheese caramelized crust at Pequod’s and then dig into ‘zah at what once was Al Capone’s speakeasy, Exchequer. And since it’s a walking tour, the calories don’t count.

The Riverwalk is a recent addition that struck ground in the early 2000s and wasn’t finished until 2017, meaning it may be new to Chicago veterans and first-timers alike. Though you could easily entertain yourself with the restaurants, bars, and boats lining the walk, this tour will help explain how the Riverwalk is one piece of a larger, metropolitan puzzle. It’s among the few tours that concisely explains how a swamp is now a skyscraper-filled metropolis.