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“It wss a great experience. MJ knows his stuff. The food is good at nice places. It was better than expected.”
Discover Chicago’s dark past with this 2-hour guided walking tour exploring gangsters, ghosts, and haunted landmarks in the South Loop district.
“Our tour was really good, I really enjoyed the stories and I saw bits of the city I wouldn’t maybe have gone to otherwise. Our guide Thalia was really knowledgeable, I had lots of questions, and delivered the stories in a funny and engaging way”
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 tour, saw amazing interiors that we would not otherwise have known about. Annie was the perfect guide - friendly, knowledgeable and had great recommendations for food & drink in Chicago. Highly recommend 😊”
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 tour and the guide was very helpful & adapted to our specific interests. Highly recommend.”
Discover Chicago's architectural gems with a 2-hour guided walking tour, exploring iconic landmarks and hidden treasures with expert commentary.
“Tour guide was amazing!!! She was super knowledgeable and had to improvise due to the Memorial Day parade and she did it without a skipping a beat!”
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.
“Adam was great. It was a perfect day for taking the pedway as it was a little gloomy and chilly outside. I'm now curious to explore more and am going to see what other tours this brand has. Keep up the good work.”
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.
“Allan did an amazing job on the WHOLE tour. Kept us informed and eager to go onto the next stop.”
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.
“Fabulous tour and Matthew was a skilled guide! Moved along at appropriate pace, showed us some stunning landmarks , was kind, humorous and knowledgeable ! This is a must do in Chicago!”
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.
“Wonderful tour! Jonathan Knotek was our tour guide. He reached out the day before and advised the details on where to meet. He was extremely knowledgeable, witty & truly made the trip worth every penny. I was a little surprised to be picked up in…”
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 seeing the city while sampling Chicago favs!”
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 your was excellent. Our your guide Bill was so knowledgeable and made the your so enjoyable. Could not recommend this your highly enough.”
Discover Chicago’s haunted sites on this 1-hour walking tour, featuring ghost stories, spooky landmarks, and historic tales in Lincoln Park for $24.
“Great guide and very informative and interesting stories. We learned new information in apart of the city that was very familiar to us! Great walk!!”
The river runs through an architecture lesson, and the lake applauds.