America · WALKING TOURS IN CHICAGO
The shortlist to send a friend: 13 walking tours in Chicago worth the money, each with its price, its traveller verdict and the thing to know before you pay.
A 2-hour Loop walk with a historian, gangster lore, and ghost stories at real downtown landmarks, plus an optional minibus upgrade.
“Very exotic experience, another good way to know about Chicago history beside just regular tourist spots”
Eat Chicago classics on an easy 3-hour Loop walk, see Millennium Park and the Pedway, then use a free 2-hour bike or kayak.
“Go hungry, plenty to eat. Our Tour guide was funny, entertaining, and very knowledgeable about Chicago.”
Chicago’s Gangsters and Ghosts walking tour mixes Al Capone tales, eerie legends, and hotel interiors in 2 hours around the Loop.
“Bella was so much fun and give a great tour. it was entertaining to hear the story while yoi are walking which make the walk seem so quick and short!”
A small-group Chicago walking tour mixing classic bites, downtown architecture, and city stories, ending near the Loop with Big Bean photos.
“It was a good way to get a feel for Chicago. I thought I had tried deep dish pizza in California, but it turns out a Chicago deep dish pizza was a true, brand new culinary experience. And I was glad I got to ride the "elevated".”
Chicago’s Secret Interiors walking tour mixes skyline highlights with rarely seen lobbies, domes, and gardens, led by a small expert group.
“We've used Viator when traveling in Europe and would have never thought to use them locally. But we did and so happy we did! Our tour guide, Ethan, was awesome. We had a huge group (40 people) and he handled the group perfectly with great enthusiasm, making sure we were always together, that we could hear him, etc. And he was super knowledgeable. Even living in Chicago our whole lives, we learned so much. Highly recommend.”
A 3-hour small-group Chinatown tour with 5 generous Chinese food stops, plus major landmarks like Nine Dragon Wall and Pui Tak Center.
“This was a wonderful cultural experience with interesting experiences and restaurants we would’ve never found on our own. Our guide was knowledgeable and enjoyed learning the history about Chicago’s Chinatown. The walking was easy and enjoyed honestly every food stop. To learn about Chicago”
Chicago Secret Interiors walking tour in the Loop. Step inside iconic buildings, spot hidden design details, learn engineering stories, 2 hours.
“Talia is terrific and we were lucky in that we were the only two people in the tour. Please do this tour!”
Chicago gangsters meet big comfort food on a 2-hour small-group walk with secret-tunnel steak, Chicago Dawg, and deep dish.
“Give Ty a big Bonus!! He was awesome! Very informative, knew the subject, added his own twist. Chantal and Jill.”
A 1.5 to 2 hour Chicago Loop mob and haunt walk with a pro guide, haunted hotel tales, Capone-era stops, and eerie alleys. Small group.
“Kevin was friendly and did a great job. Very knowledgeable and full of interesting stories. I would recommend this tour.”
A 2-hour Chicago architecture walk of Michigan Avenue and the Loop, with Chicago Architecture Center galleries and Chicago Cultural Center interiors.
“What an amazing tour! Our guide Jim was so friendly and informative! We had already done other architecture tours so we were not too sure if this would be appealing to us but hands down it was awesome!! Definitely would recommend it and will definitely be signing up for additional tours around town. Was shocked how many times I had been in Macy's and never looked up!”
Chicago Pedway secrets tour with underground passages, stained-glass interiors, and public-art clues on a 2-hour walk near Millennium Park.
“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.”
A 2.5-hour Lincoln Park booze and boos walking tour with period-dressed guides, classic bars, and Chicago ghost stories for $35.87.
“Great walk around a beautiful town with some interesting stories. The guide was very entertaining and expressive when telling them. Seeing the sights where these events hppend made it all the more exciting. The bars were interesting, and who doesn't love booze?”
A 2-hour Chicago River North walk mixing mob stories with three tastings: deep dish and tavern-style pizza, steak, and a Chicago hot dog.
“The Chicago Gangsters and Food Tasting tour was a highlight of our trip. Our tour guide Talia was very knowledgeable, and the food was excellent. There were many great photo opportunities and activities recommended to take in the complex social and cultural nuclei of the city.”
Every kind of day out, and the best of each.
