Chicago
The walking tours: Loop interiors, the underground Pedway and lobbies that double as marble museums. Chicago hides its best rooms behind ordinary doors, and the guides hold the keys.
Explore Chicago’s top sights and iconic foods on this 3-hour walking tour, including deep-dish pizza, hot dogs, and scenic landmarks, with expert guides.
Most Popular“Fran did an amazing job sharing her city with us! She brought us to all of the popular spots and the food was amazing.”
Discover Chicago’s dark past with this 2-hour guided walking tour exploring gangsters, ghosts, and haunted landmarks in the South Loop district.
“Tanner was amazing. Even though we were only two people at our tour, he gave us the full experience. It was fun, interesting and informative. The 1.30 ish hours went by like nothing. One of the best tours we’ve taken.”
Discover Chicago's vibrant Chinatown through a 3-hour guided walking tour featuring authentic food tastings, cultural insights, and historic sights.
“Amazing tour guide named Wyatt. The tour was great. The food was amazing. They were accommodating to food allergies”
Explore Chicago’s secret interiors on a 2-hour walking tour, discovering hidden architectural details and stories with passionate guides for just $36.
“Our tour guide - Grant was super awesome. He let us know so much history of the city and its intricate architecture all along the downtown area.a”
Explore Chicago's dark side with this mob and haunt walking tour. Discover haunted hotels, mob hangouts, and supernatural stories for an authentic experience.
“had Alyssa. She was a great guide. Very knowledgeable and excited to share the information. She was very personable as well. Tour stuck to the theme very well and there were plenty of interesting facts that I was never aware of. The history of Chicago…”
Discover Chicago's architectural gems with a 2-hour guided walking tour, exploring iconic landmarks and hidden treasures with expert commentary.
“Our tour guide John was extremely knowledgeable about the history and architecture of Chicago. We’re very glad we did the tour.”
Discover Chicago's underground Pedway and hidden secrets with this 2-hour guided walking tour for just $35, perfect for architecture lovers and curious explorers.
“Navigating through the Pedway isn’t as straightforward as it seems. Genuinely appreciate the insight the guide given us on this underrated utility as well as niche knowledge of the city’s history.”
Discover Chicago's haunted past on this 2.5-hour ghost pub crawl, exploring historic bars, spooky stories, and hidden city corners with a lively guide.
“Highly recommend! Katie did a great job! Very informative and fun. A wealth of knowledge. Good rapport with your group.”
Discover Chicago’s gangster past and iconic foods on this 2-hour walking tour with tastings, historic hideouts, and stories of Capone’s era.
“our guide Baylor was very knowledgeable about the sites we visited and was an overall great guide. All the food was also really good, the mix of eating and walking around was really comfortable since it was not a very long distance between stops.”
Explore Chicago's architectural gems from the Golden Age on a 2-hour guided walking tour, featuring landmarks like the Chicago Cultural Center and Marshall Field's.
“Excellent tour with a phenomenal guide. Ron is very knowledgeable and approachable. We highly recommended this tour to anyone interested in architecture.”
Discover Chicago’s architectural gems on this 1.5-hour guided walking tour, perfect for first-timers and time-pressed visitors eager to see iconic buildings and learn their stories.
“My husband and I had a wonderful time at this tour. Our guide was very knowledgeable and fun. I definitely recommend.”
Discover Chicago's Prohibition era on a guided speakeasy tour—choose walking or bus options, visit historic bars, and learn about gangsters, politicans, and more.
“we had a great time on the tour on 1/11/26. Thanks Jonathon for being flexible and converting the bus tour to a “private “ walking tour. We learned so much through your story-telling of the prohibition period to present day in Chicago. You were great!…”
Discover Chicago's iconic flavors and sights on a 3-hour guided food tour, with free bike or kayak rentals, led by friendly, knowledgeable guides.
“Loved how knowledgeable and personable the guide was. Great job by Gabe and Cynthia”
Explore Chicago’s stunning Art Deco skyscrapers on a 1.5-hour small-group walking tour. Discover hidden gems, interiors, and history with expert guides.
“Robin was exceptional! Very knowledgeable of the buildings we toured, engaging with our group, and informative of the history of Chicago and its architects. She is very clearly passionate about what she does and we look forward to booking another tour when we visit Chicago…”
Discover Chicago’s haunted sites on this 1-hour walking tour, featuring ghost stories, spooky landmarks, and historic tales in Lincoln Park for $24.
“Amazing tour! He was so knowledgeable about the city ghost experience I would definitely recommend :)”
The river runs through an architecture lesson, and the lake applauds.