The 5 Best Free Walking Tours In All Of Chicago, According To Popularity Ratings

Nothing beats getting to know a destination one street at a time, slowly falling into the rhythm, pace, and movements of the city and its quirks. Anyone who has traveled to Chicago will assure you that the city has many interesting corners and cool things to casually stumble upon. From vintage Chicago mansions to super trendy breweries, the city is not only walkable, but generous with sights to marvel at. A walking tour is one of the most effective ways to get your head around the history, local treasures, and best places to tuck into a Chicago-style hot dog or deep-dish pizza that only Chicagoans could get the inside scoop on.

Lucky for the hoards of tourists that show up keen to see what's in store, the Windy City is full of walking tours to satisfy all types of interests. You can find walking tours for all major parts of the city, sometimes for free. Budget-travelers, history buffs, and even those who want to get to know their home cities' hidden history all make the most of free walking tours. With the only expense being an optional tip for the tour guide, walking tours are becoming popular in the city, especially during the warmer months. We looked through the most highly rated and commended tours to get an idea of the best ones worth checking out when visiting the Second City.

Free Chicago Walking Tours is one of the most popular year-round walking tours in the city. The tours are led by a team of Chicago natives ready to share their love of the eclectic cultural hub that is Chicago. The interactive tours are built with both tourists and Chicagoans alike in mind, for an enriching and intercultural exchange that will change the way you experience Chicago. This tour is a great way to begin your trip in Chicago to get an understanding of the history that makes Chicago so diverse and unique.

Tours last around two hours and rarely exceed one and a half miles. Some of the most popular tour routes include the most well-trodden ones such as the Loop, Chicago River, Millennium Park, Michigan Avenue, and Lincoln Park as well as some opportunities to veer off the beaten path to get to know the communities and local business that make up some of Chicago's most precious histories and businesses. One of the most popular tours is the Chicago Crime & Gangster Tour where some of the names you might have heard of like Al Capone, Dean O'Banion, George "Bugs" Moran, "Machine Gun" Jack McGurn, and Sam Giancana come to life vividly while you walk the same streets that they did. The pay-what-you-like system allows visitors to choose how much they would like to value the tour.

The Chicago Greeter tours focus on connecting some of Chicago's friendliest locals with visitors ready to fall in love with the parts of the city only a city-dweller could recommend. The tours are divided into several categories to cater to different travel styles. You can enjoy a customized neighborhood tour, join one of the regular downtown walks, or opt for a self-guided tour to explore at your own pace. With intimate-sized groups (tours typically welcome 6 guests max), it's the perfect way to get to know the intricacies of the city and get your questions answered (like figuring out some of the unwritten rules for visiting Chicago that tourists trip up on).

The tours last between two to four hours for the Greeter walk with a local guide and roughly one hour for the InstaGreeter walk — a shortened version of the tour. Tours can accommodate 10 languages, 40 different interest types, and 25 neighborhoods across the city. When you join a Chicago Greeter tour, you can expect everything from lesser-known, off-the-radar recommendations to historically significant stops. The tour guides (your Greeters) follow a no-tipping policy, which means that this free tour guide is a reflection of the friendly Chicagoan charm. Tours include 'The Loop', which runs all year round from 11:30 am to 1:30 pm Friday-Sunday, the Chicago River walk from 11:30 am Friday-Sunday, and pop-ups throughout the year.

The beauty of wandering around Chicago as a first-time visitor is never being short on itinerary options. The city spoils you with attractions, but gaining insight from someone who intimately knows where the artsiest and trendiest neighborhoods in Chicago (and in the world) can be found is what's truly worth it. That's where Free Tours by Foot come in. Free Tours by Foot has been making it easy to learn about Chicago with fellow travelers since 2007. The tours cover a range of interests and routes, such as the Loop and Millennium Park tour, the Riverwalk and history tour, as well as the Haunted History tour. There is also the option to join seasonal tours, such as the Chicago Pedway Tour in the winter. Deep dive into the historical highs and lows of the city, as well as into the recommendations from expert guides on what to see and do in Chicago for a good time.

Tours by Foot also offers guides and other ticketed specialty walking tours and unique experiences. Offering daily tours in over 50+ cities for over 3 million guests, it is dedicated to making local knowledge accessible and super enjoyable. Free Tours by Foot offer year-round tours and use a pay-what-you-want system to tip guides after a day spent wandering the city.

Chicago has made its mark as one of the places in the country to geek out on architecture. As the birthplace of the skyscraper, as well as being home to some Prairie-style buildings across the city, there is much to see. The Chicago Architecture Center (CAC) is the best place to receive a tour around the city to discover the stories woven into each brick and corner of Chi-Town. As a non-profit, the CAC is dedicated to giving back to Chicago while showcasing the design that makes the city so culturally relevant and highly visited.

While the tours at the CAC are ticketed, purchasing a membership allows visitors to gain free access to the essential walking tours. It works especially well for Chicagoans or those who enjoy the Windy City and find themselves making regular trips. The ticket and membership funds go directly back into the community, with one walking tour ticket providing transportation and lunch for a CAC summer program student. The essential walking tour membership also provides discounts on premium walking and boat tours, as well as buy-one-get-one tickets for the CAC River Cruise. The cruise was voted best boat tour in the U.S. by USA Today readers and best tourist attraction in the city in 2024. The essential walking tours depart from 111 East Wacker and are held by CAC volunteers expertly trained in architecture and history.

For those who enjoy wandering around solo, moving as fast or slow as their time allows, MetroWalkz is the self-guided mobile tour to have on your radar. With a smartphone on hand, you'll be able to enjoy an informative walking tour with simplicity and the ability to make as many stops and detours as your heart desires. The tours are easy to use and include maps and insider narratives to learn more about the aspects of the city that most interest you. MetroWalkz makes touring uncomplicated with insight on nightlife, dining, museums, and the many cultural sites and historical buildings.

The tours include Architecture, Millennium Park, Navy Pier, Magnificent Mile, Museum Campus, Grant Park / Art Institute, Chinatown, Old Town, Gold Coast, and West Loop. MetroWalkz is recommended for those who prefer moving through the city on their own schedule or maybe have limited time but still want to see what Chicago's hidden and much-loved attractions have to offer. The tours are accessible through eVisitorGuide.com.

With a city like Chicago, it's easy to get lost in the sea of travel reviews and recommendations; after all, the internet is full of strong opinions about the city and its absolute "must-do" activities. We scoured through travel boards like Yelp and TripAdvisor and recommendations from Chicago tourism boards, such as Choose Chicago, to present the most popular free walking tours. While walking tours are plentiful in the city, we spent time sifting through them to highlight the ones that had high ratings and/or featured in several lists and trustworthy publications. 

We wanted to name walking tours that were trusted by travelers as well as by the sites that want to represent the best of tourism services in the city. Chicago remains a coveted destination for many international and local travelers, and if you're going to walk the historic streets, it's best to do so with some of the most popular and knowledgeable experts whose job it is to walk the walk and talk the talk, Chicago style.