The 7 Best Chicago Walking Tours
See the best Chi-Town has to offer on your own two feet.
Discover the hidden details of the Windy City's famed architecture with a tour from Inside Chicago.(Courtesy of Steven Sabourin/Inside Chicago)
Note: Some tour providers on this list may have ceased operations due to COVID-19. Check with your tour operator about availability before you book.
The Windy City is known for its interesting architecture and landmarks, its deep-dish pizza and specialty hot dogs and its many loyal sports fans. However, getting a real feel for Chicago can be difficult if you only hit the main attractions or you spend your entire trip in a single neighborhood. To gain a local's perspective, book a guided walking tour. Factoring in both traveler sentiment and expert opinion, U.S. News selected these seven tours as the best walking tours available in Chicago.
Inside Chicago – Open Your Eyes: Inside the Pedway & Other Secrets of the Loop
This two-hour tour takes you throughout the city's famous Pedway (an underground network of tunnels that connects more than 50 buildings) to see the details hidden in its architecture. During the 1 1/2-mile walk, you'll also see above-ground treasures, such as a Picasso statue and a 1920s-era church, and venture into a few buildings that connect to the Pedway. Throughout the tour, helpful guides share stories of the city. Reviewers call this tour informative and surprising. Walks are offered at 2 p.m. on Monday and Friday, and tickets start at $30 for adults and $25 for seniors and children ages 5 to 10. Other public tours from Inside Chicago include tours of individual neighborhoods and a seasonal Christmas outing.
Chicago Detours – Historic Chicago Walking Bar Tour
Visitors with an interest in Chicago's Prohibition-era history will want to sign up for this 2 1/2-hour walking tour. Stops for drinks and snacks include Billy Goat Tavern, a bar inside a 19th-century mansion and a Jazz Age hotel. In between stops, patrons learn all about Prohibition, jazz music and the city's world-renowned architecture. Travelers say this is a must-do and applaud the informative guides. Tours are bookable at 5:45 p.m. on Thursday and Friday, 2 p.m. on Saturday and 3 p.m. on Sunday. Tickets start at $36 and include snacks, but not drinks. Chicago Detours also offers a tour about the 1893 World's Fair and an architecture tour.
Chicago Food Planet – Gateway to the West Loop Food Tour
Chicago has long been considered one of America's best foodie destinations. To sample some of the city's best bites, consider this tour from Chicago Food Planet. Tastings rotate, but foods could include Mexican fare, doughnuts, pizza, meatballs, beer and hamburgers. As you eat your way through the West Loop, guides share stories about the neighborhood's history and culture. Travelers advise coming hungry as there are plenty of samples. Tour availability changes seasonally, but tours generally start at 1 p.m. several days a week and last three hours. Tickets start at $60, but you can upgrade your package to include three drink pairings for around $80 per person. Youths ages 12 and younger can also tag along for $35 each. Chicago Food Planet also offers tasty trips through Wrigleyville and Navy Pier, among other options.
Free Tours by Foot – Lincoln Park Blues and Gangster Tour
Ideal for visitors interested in an in-depth overview of Chicago's famous Lincoln Park neighborhood, this two-hour, mile-long walk earns high marks from reviewers. Guides teach patrons about the history of the neighborhood and the city's infamous gangsters while making stops at DePaul University, the Red Lion Pub and Oz Park, among other landmarks. Patrons say this trip is informative and that they loved seeing more of Lincoln Park. This tour is free to take, although you can decide to tip your guide however much you want at the end. Tour times and dates vary and reservations are required. Free Tours by Foot also operates tours of Millennium Park, a ghost tour and tours of the Riverwalk, among other options.
Chicago Gangsters and Ghosts Tour
Patrons say this guided walk is great fun and praise guides who expertly mix humor and gruesome stories. You will walk approximately 1 1/2 miles in two hours while exploring haunted locations and old crime scenes where some of the city's most famous misdeeds played out. Historians are your guide, so you will learn the real story behind shady deals and infamous Chicago gangsters like Al Capone. Tickets start at $27 for adults, $25 for seniors ages 65 and older and $17 for youth ages 7 to 17. Children ages 6 and younger can tour for free. Tours depart daily at 11 a.m. and at 1, 4 and 8 p.m.
Bobby's Bike Hike – Chinatown Food & Culture Walking Tour
Eat your way through Chinatown on this tour with Bobby's Bike Hike. In 2 1/2 hours, you'll sample delicacies that represent five different regions of China while guides share the history of Chinese immigration to Chicago. Tea, Szechuan chicken, hot pot, dim sum and baked goods are just some of the treats you could try during the trip. Patrons say the outing is full of incredible food and history. Prices vary depending on the day you tour, but you can expect to pay around $55 for adults and $50 for children. Tours depart at 4 p.m. on Friday and Saturday. Bobby’s Bike Hike also offers a dessert walking tour and various bike tours, among other options.
Free Chicago Walking Tours – Riverwalk & North Loop Tour
This two-hour tour details Chicago's history from the late 1600s to the present day, discussing the Revolutionary War, 1915's Eastland disaster and everything in between. As you walk, you'll see the Chicago River, the Jewelers Building, Heald Square Monument, the Chicago Cultural Center, Daley Plaza and an array of other important landmarks. Reviewers appreciate the pace of this tour and its knowledgeable, thoughtful guides. Your only cost is what you decide to tip your guide at the end. Free Chicago Walking Tours also operates trips through Millennium Park and walks that guide you through less touristy parts of the city, among others.
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