The 5 Best Chicago Walking Tours, According to Reviews

The Windy City is known for its interesting architecture, deep-dish pizza, specialty hot dogs and many loyal sports fans. However, getting a real feel for Chicago can be difficult if you only hit the main attractions or spend your entire trip in a single neighborhood.

To get a local’s perspective, book a guided walking tour. Factoring in both traveler sentiment and expert opinion, U.S. News selected the following as the best walking tours available in Chicago.

Best Architecture: Inside Chicago – Open Your Eyes: Chicago’s Underground Pedway & Other Secrets of the Loop

Price: Adults from $30; kids from $25
Duration: 2 hours

This 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 1.5-mile walk, you’ll also see above-ground treasures, such as a Picasso statue and a 1920s-era church, plus venture into multiple buildings that connect to the Pedway. Throughout the tour, helpful guides share stories of the city. Reviewers call this tour informative, unique and surprising, and recommend it if you’re looking for both locals and visitors.

Walks are offered at 2 p.m. Thursday through Tuesday, with an additional 10 a.m. tour on Fridays and Saturdays. Other public tours from Inside Chicago include tours of individual neighborhoods and a seasonal Christmas outing.

Best Food: Chicago Food & City Tours – Gateway to the West Loop Food Tour

Price: Adults from $85; kids from $50
Duration: 3 hours

Chicago has long been considered one of America’s best foodie destinations. To sample some of the city’s best bites, consider this outing led by Chicago Food & City Tours. Tastings rotate, but foods could include bites of burgers, pizza, craft beer and more. As you eat your way through the West Loop, guides share stories about the neighborhood’s history, culture and architecture. In total, you’ll walk a little over half a mile.

Travelers advise coming hungry, as there are plenty of samples. Along with the hearty food portions, reviewers also praise the incredible guides, who they describe as passionate and knowledgeable.

Availability changes seasonally, but tours generally start at 4 p.m. on Saturdays and 1 p.m. on Sundays. More tours may be offered in the warmer months. Tourgoers who choose the alcohol package will enjoy three drink pairings with their food, at an additional cost. The company also offers tasty trips through Chinatown, an outing inspired by “The Bear” (an FX Original TV show) and other options.

Best Ghost: Chicago Gangsters and Ghosts Tour

Price: Adults from $35; kids from $17
Duration: 2 hours

Two tours in one, this 1.5-mile stroll through the Loop transports travelers back to the Roaring ’20s, when gangsters and bootleggers used the speakeasies and underground tunnels in this part of the city for their misdeeds. Tourgoers will explore haunted locations and old crime scenes, such as the Palmer House (now a Hilton hotel), the Congress Plaza Hotel (believed to be haunted by Al Capone’s ghost) and Death Alley. Travelers say this tour is great fun, praising the energetic guides, who expertly mix humor and gruesome stories, and manage to keep even hard-to-please teens engaged.

Tours depart daily at 11 a.m., 1 p.m., 4 p.m. and 8 p.m. Children 6 and younger can tour for free. The company also offers a gangster-themed food tour.

Best Chinatown: Bobby’s Bike Hike – Chinatown Food & Culture Walking Tour

Price: Adults from $75; kids from $65
Duration: 2.5 to 3 hours

Eat your way through Chinatown on this milelong tour with Bobby’s Bike Hike. You’ll sample delicacies that represent five different regions of China while guides share the history of how Chinese immigrants shaped Chicago’s culture and dining scene. Tea, spicy chili chicken, noodles, dim sum and baked goods are just some of the treats you may try during the trip. Patrons say the outing is full of incredible food and history.

Tours typically depart daily at 11:30 a.m. An additional 5:30 p.m. tour is typically offered on Thursday, Friday and Saturday. Bobby’s Bike Hike also offers Chicago outings via bike and kayak, plus tours through some of the top attractions in Miami.

Best Free: Free Chicago Walking Tours – Riverwalk & North Loop Tour

Price: Free
Duration: 2 hours

This 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. Many reviewers recommend taking this tour on your first day in the city, saying it will help you get your bearings and provide context for the rest of your trip.

Tour schedules vary by month. Your only cost is what you decide to tip your guide at the end of the tour. Free Chicago Walking Tours also operates trips through Millennium Park and less touristy parts of the city.