Chicago · WALKING TOURS
The Loop is a grid you can learn in an afternoon with the right guide. These 15 walks cover the architecture, the crime history, the murals and the food, each with its distance, its duration and its price.
Chicago Loop bootleggers, ghosts, and Al Capone lore, guided by a historian. Walk key landmarks, plus optional minibus upgrade.
“Taka was our guide and she was fantastic. We had such a good time, she was a very good story teller, loud and clear. Lots of interesting information. We learned alot and had a lot of fun.”
Chicago’s classic foods meet downtown landmarks on an easy 3-hour walk, with tastings included and a free bike or kayak bonus.
“The tour guide was great and since we were charged the entire fee but didn’t get to see everything without warning that booking on New Year’s Day tour one tour stop food place would be canceled. That was disappointing. But you all can use that extra we didn’t use for that place and give to our tour guide lady as her tip. She was with Gabe from Bobby bike and hike tours 11:30 tour on 1.1.2026. She was trying to be as enthusiastic and did explain as much about Chicago but we just wanted to go sit down and eat at places :) And they were nice places to stop…”
Chicago South Loop gangsters and ghosts guided walk with a historian, inside hotel stops, Riverwalk and Death Alley stories, 2 hours.
“Bailor was our guide and she’s the best! Super interesting and fun. We were happy to learn new things of Chicago.”
Taste Chicago classics and see major architecture fast on a small-group Loop walk with the Pedway and Millennium Park’s Bean.
“Excellent Tour guide. David was so knowledgeable, patient and helpful. I was on a rolator David knew exactly where the elevators were located. By preparing for the locations, it made everyone comfortable.”
Chicago Secret Interiors walking tour shows you Loop skyscrapers and rare opulent interiors for about 2 hours, $35.
“A master class in history, architecture and art. Ethan is a fabulous guide. Smart, clear, relatable. We learned so much. He was undeterred by heavy rain and needing to negotiate his umbrella with one arm in a sling. Incredible experience.”
Taste dim sum, hand-pulled noodles, Xi'an lamb flatbread, Sichuan chicken, and Portuguese egg tarts, plus Chinatown landmarks on a 3-hour walk.
“Fantastic tour! Fascinating insight into both chinese food and history. Jeff was our guide and made everyone feel extremely welcome. Highly recommend fitting this into your visit to Chicago.”
Chicago Secret Interiors tour for $35, a 2-hour Loop walk to see domes, mosaics, and the engineering stories behind icon buildings.
“It was a very informative tour with beautiful buildings and a funny, knowledgeable guide.”
Prohibition tales plus Chicago classics on a 2-hour small-group walk featuring steak, Chicago dawg, and deep dish stops.
“Loved learning the history of the Irish North and Italian South gangs and the clever ways they stuck it to each other. Pizza was phenomenal, and Harry Carrys basement was so interesting with the tunnels!”
A mob and haunt walking tour through Chicago’s Loop, with eerie hotel stories, the Alley of Death, and guided history for $34.
“Great experience! Our guide, Justin, was very entertaining and knowledgeable. The walking was not extensive.”
Chicago architecture walking tour from the Chicago Architecture Center to the Loop, with art deco interiors, small-group guides, and included galleries.
“John, our docent, was great - the tour was super interesting and he really took the time to answer questions and being the buildings to life. Thank you for a great tour”
Chicago Pedway tour with secret passages, stained glass interiors, and hidden art meanings. Learn the system, then tackle tricky sections.
“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.”
Haunted Chicago Booze and Boos tour mixes Lincoln Park ghost stories with pub stops. 2.5 hours, local guide, drinks extra.
“We booked last minute on our last night of our vacation and it was a great decision! Lara was our tour guide, she brought the stories, the jokes! Would definitely recommend this experience to everyone!”
Chicago gangster lore meets food tastings in River North on a 2-hour walk. Three stops include deep dish pizza, steak, and a hot dog.
“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.”
Two hours walking Chicago’s Loop with a CAC guide, spotting Golden Age landmarks like the Tiffany dome and Palmer House.
“It was interesting to know about those buildings which, after a first impression, looked unimportant. The guide was very nice and helpful!”
A fast, small-group walk through Chicago’s architectural timeline, starting at the Chicago Architecture Center, with included gallery admission.
“Perfect tour. Well thought out. Loved the history woven in. So interesting that I took notes! And our docent was so approachable and entertained numerous questions from numerous attendees.”
Every kind of day out in the city, and the best of each.
