The Best Walking Tours in Chicago

Chicago skyline
Chicago skyline | © Bruce Leighty / Alamy Stock Photo
Mason Johnson

Even native Chicagoans have trouble exploring the city’s 77 neighborhoods, each community its own odd microcosm. Whether you’ve lived here your whole life or are visiting for a few days, there’s a walking tour that will wear out your soles and teach you something new. Below, you’ll find tours covering a range of subjects, from architecture and pizza to ghosts and street art.

From swamp to skyscrapers

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, a tour from Chicago’s Finest Tours will help explain how the Riverwalk is one piece of a larger, metropolitan puzzle through their #1 History Tour. It’s among the few tours that concisely explains how a swamp is now a skyscraper-filled metropolis. The tour takes place every Saturday in the summer and costs $25 for adults.

Looking down onto the Riverwalk in downtown Chicago

An architectural primer

Chicago’s eclectic architecture could consume an entire trip to Chicago. A good primer is Chicago’s Finest Tour’s Architecture 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. The tour takes place on sporadic Fridays and will run you $25.

Skyscrapers in Chicago

Offbeat street art

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.

Lion statue in Chicago

From factories to calories

Chicago Detours has been operating for nearly nine years and highlights the intricacies of individual neighborhoods’ stories. Their tour Factories to Calories: Fulton Market examines a West Side neighborhood that was once known for its slaughterhouses and is now a haven for up-and-coming restaurants. You can depend on Chicago Detours to tell it like it is, which is to say, to highlight the gritty aspects associated with changes in a neighborhood. Oh, and they’ll feed you artisanal deli meats from the likes of Publican Quality Meats. The two-hour tour only covers about one mile and costs $42.

Buildings in Fulton Market neighbourhood

History and booze

For a well-rounded taste of Chicago’s boozy past, Chicago Detours doesn’t hold back during their Historic Chicago Walking Bar Tour. Taking place across downtown and River North, the tour touches on a slew of subjects, from the ‘Curse of the Billy Goat’ to jazz, along with breweries and Prohibition. Food, beer, and wine enhance the historical facts you’ll discuss with the tour guide. The tour takes place Monday, Thursday, Friday, Saturday and Sunday and costs $38. Additional charges for beer and wine may apply, depending on your thirst.

Irish bar in Chicago

Walking Tour of Lincoln Park in Chicago

North of downtown sits Lincoln Park, a wonderland of historic homes. It also boasts the largest park in the city, making the Walking Tour of Lincoln Park ideal for a sunny afternoon. A local guide will show you decrepit graves, America’s oldest zoo and more. The tour takes place every day but Sunday and costs $30.

Skyline and family on The Nature Boardwalk at Lincoln Park Zoo in summer, Chicago

The dazzling interiors of the Loop

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 skyscrapers

Secret gardens, live music and fireworks

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. Enjoy this tour on Wednesday nights. It costs $30 per person.

Chicago Skyline at night

Chinatown adventure for foodies

Chicago Food Planet’s Chinatown Adventure Food Tour paints a picture of Chicago’s Chinese culture through the exploration of five different restaurants. Gorge on authentic cuisine from the Canton, Mandarin and Szechuan regions of China while also exploring a Buddhist Temple and Ping Tom Memorial Park. The tour occurs on Saturdays and Sundays and costs $70 for teetotallers and $90 for those who imbibe.

Ping Tom Memorial Park in Chicago’s Chinatown

Walk among unmarked graves

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.

Headstones in Chicago Cemetery

Chicago for Chicagoans Walking Tours

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.

Aerial view of the Pilsen neighborhood

A modern walking tour

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. Both tours cost $26.

Example of the modern architecture in Chicago

Pizza City, USA

Abandon your preconceived notions of Chicago-style pizza before embarking on this tour – Pizza City, USA shows off the diversity that exists in Chicago’s pizza scene. Though both their West Loop and Wicker Park tours feature Chicago deep-dish pizza, they’ll also highlight restaurants that serve ‘only-in-Chicago’ Roman al taglio, classic Neapolitan and Sicilian slices. The Wicker Park tour currently takes place on Sundays and costs $49.

Famous Pizza Uno restaurant in Chicago city

Travel back to 1893

Experience the 1893 World’s Fair through the greatest invention of all: food. Though food is the focus, Tastebud Tours will also teach you about historic Chicago as you visit the Private Cliff Dwellers Club, The Berghoff – whose founder exhibited his beers at the World’s Fair – and The Pittsfield Building. The tour takes place most Fridays and Saturdays and costs $68.

The Berghoff Restaurant in Chicago

This article is an updated version of a story created by Katie Mastropieri.

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