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.
“Lillie was amazing. She was very personable, had several great one liners and was even more knowledgeable about the history. The tour was an easy walk and a great time for anyone visiting for a first time or if you just want to try something…”
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 guide Grant was fantastic! My friend and I took the tour on a cold February day and enjoyed every minute of it. Grant is very personable and knowledgeable. The architectural details we saw were stunning. Definitely recommend this tour!”
Explore Chicago's dark side with this mob and haunt walking tour. Discover haunted hotels, mob hangouts, and supernatural stories for an authentic experience.
“Very interesting and Bryson was great! The walk was fun and hearing stories at the location was perfect.”
Discover Chicago's architectural gems with a 2-hour guided walking tour, exploring iconic landmarks and hidden treasures with expert commentary.
“We loved our guide Laurel. She was so knowledgeable and fun. Great tour. We would highly recommend this 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.
“Really enjoyed the Chicago medway tour. Henry, our tour guide was excellent. Very knowledgable and had a background in architecture which made for a very informative experience. I recommend this tour.”
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.
“Was doing a solo train trip cross country and did this on my own. Made me feel welcome and had an amazing time learning about the city’s haunted past.”
Discover Chicago’s gangster past and iconic foods on this 2-hour walking tour with tastings, historic hideouts, and stories of Capone’s era.
“Talia was a mega tour guide, so much knowledge and funny. There was just the right amount of food stops/talking - loved it!”
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.
“Ingrid was a great guide. She provided information in a natural vs a rehearsed way. She also paused and gave us enough time to think of questions. I also appreciated that she used a microphone system so that we could wander around to look at…”
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.
“We were visiting for two days from London- excellent knowledgeable walking guide. Loved all the quirky facts about various iconic buildings. Added bonus to be able to view the foyer of the Automobile association building.”
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.
“Tour was amazing. Very informative with a witty blend. Definitely recommend!”
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.
“This tour is a must on a visit to Chicago... so much of the city's earlier 20th century history is captured in this tour of the moderne art deco architecture. One does not tend to appreciate these gems hidden among the neo-classic buildings and glass…”
Discover Chicago’s haunted sites on this 1-hour walking tour, featuring ghost stories, spooky landmarks, and historic tales in Lincoln Park for $24.
“They should improve their storytelling and do more research. Our guide was very friendly and enthusiastic.”
The river runs through an architecture lesson, and the lake applauds.