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“Gabe gave us a great tour…not only food but the city, the architecture and history of the city. My husband and I cannot recommend this tour enough. Ask for Gabe!”
Discover Chicago’s dark past with this 2-hour guided walking tour exploring gangsters, ghosts, and haunted landmarks in the South Loop district.
“Bailor was our guide and she’s the best! Super interesting and fun. We were happy to learn new things of Chicago.”
Discover Chicago's vibrant Chinatown through a 3-hour guided walking tour featuring authentic food tastings, cultural insights, and historic sights.
“Our guide did a great job and provided a good mix of cultural information, history and descriptions of the food. Everything was delicious and opened us up to a new part of town!”
Explore Chicago’s secret interiors on a 2-hour walking tour, discovering hidden architectural details and stories with passionate guides for just $36.
“Great! Fun and educational. Talia is so knowledgeable and kind.”
Explore Chicago's dark side with this mob and haunt walking tour. Discover haunted hotels, mob hangouts, and supernatural stories for an authentic experience.
“Mitch was a terrific tour guide. Great insider stories about ghosts...and more importantly...the mob within the historical context of Chicago. Learned much and also got to see some of the more interesting architectural and historic Chicago landmarks.”
Discover Chicago's architectural gems with a 2-hour guided walking tour, exploring iconic landmarks and hidden treasures with expert commentary.
“All tours were great--Dash, Grant and the 3rd tour I took. The Architectural River tour w/ Wade was fantastic”
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.
“We really enjoyed the Underground Walking Tour with Colleen. She did a great job of pointing out "Hidden treasures in plain site". We'll be looking around Chicago for the "y" for Wolf Point. The Ped Way is a great place to enjoy Chicago away from…”
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.
“Bobby Thomas was our guide. Although new to Chicago, he was very knowledgeable in history. We enjoyed hearing the stories, and the drinks along the way were a fun bonus. We all enjoyed each other’s company so much that we went to eat together afterward,…”
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 Alan was fantastique and very interesting and funny , the good was very good . Thank you”
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.
“The guide (John) had a lot of information. He let us go inside some of the buildings which was nice and a great experience. Would definitely recommend. As a solo travel I find group tours fun and this one definitely was. I went on a…”
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.
“Excellent tour guide! Informative. Went through Chicago's architectural history in chronological order.”
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.
“John was great! Tour was packed with knowledge but presented in a casual fun way that kept everyone engaged!”
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.
“Great tour, Jeff was an awesome guide! Learned a ton about Chicago, food was all delicious and full sized servings, we had a blast. Would highly recommend!”
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.
“Look up and see what you are missing. Chicago is graced with many beautiful buildings and the fine details of the Art Deco structures abound in downtown.”
Discover Chicago’s haunted sites on this 1-hour walking tour, featuring ghost stories, spooky landmarks, and historic tales in Lincoln Park for $24.
“Walking, historical tour of Lincoln Park. Dillinger death location, Valentine’s Day massacre location. Several reported haunting locations. Guide Rachael was great.”
The river runs through an architecture lesson, and the lake applauds.