CHICAGO · ILLINOIS
The best of Chicago.
The 15 best walking tours in Chicago, with honest prices, run times and who you book through. Which ones are worth your time downtown, and what each one actually gets you.
A historian-led Chicago Loop walk mixing Prohibition-era mob stories and reported ghost sites, with optional minibus upgrade for $52.
Most Popular“The guide had a loud voice so everyone could hear and she spoke fast and clear. The tour was interesting, so happy I booked it”
Taste Chicago classics on a 3-hour walking tour with deep-dish, Italian beef, hot dogs, brownie and popcorn plus a free 2-hour bike or kayak.
“The food was great! We had pizza, hotdogs, Italian beef, popcorn and brownies. The tour guide Kevin was so nice and informative!”
Join a historian-led Chicago South Loop tour blending gangster lore and ghost stories, with stops at Riverwalk, theatres, and haunted hotels.
“Tanner was really nice Guide. It was a good interesting tour, with much of deap facts.”
Deep-dish, hot dog, Italian beef and Chicago skyline stories on a small-group 4.5-hour walk with the Pedway and The Bean.
“Dash was fantastic! He loves the City and showed us hidden treasures I’d never seen after traveling to Chicago for nearly 25 years. He pointed us to a list of his favorite off the beaten track finds, so I’d say START your stay in Chicago with this tour. You will NOT be disappointed. He took…”
Chicago Loop interiors and skyline views on a 2-hour walking tour with rare access to lobbies, domes, mosaics, and iconic landmarks.
“Ethan was hands down the most enthusiastic and informed tour guide I’ve had the pleasure of adventuring with. I’ve done many guided tours but his passion, energy, and knowledge were truly unparalleled. Cannot recommend the tour highly enough, and Ethan even more so.”
Taste regional Chinese dumplings, noodles, Sichuan heat, and Portuguese egg tarts on a 3-hour Chinatown walk with landmark stops.
“This tour was fantastic! Our guide, Greg was fun, knowledgeable and informative. My husband and I loved everything about this tour and learning about China town. The food was fantastic!”
Chicago Loop secret interiors tour: $35, 2 hours from Union Station to iconic landmarks. Learn how light and structure shaped the city.
“Angel was very knowledgeable and we learned so many interesting things about the history of Chicago architecture! If you go in winter- bundle up. 90% spent outside. Overall great experience.”
Prohibition-era gangster stories meet Chicago food in 2 hours. Small-group walk with Harry Caray steak, deep-dish pizza, and dawgs.
“Had a great tour with Baylor. We were the only ones on this tour so had all of her knowledge directed at us only. Interesting tour and Baylor was very chatty and friendly!”
Chicago Mobs and Haunts walking tour mixes Capone hangouts, haunted hotels, and ghost stories in the Loop for $34 in under 2 hours.
“Unfortunately was not what I expected. Lots of talking & walking. No actual indoor sight visits just from afar. Guide spoke too fast.”
Historic treasures of Chicago on a small-group 2-hour walk: CAC galleries, Wrigley Building views, Palmer House lobby, Cultural Center.
“Bob was great! We learned a lot and truly enjoyed the tour. Highly recommend to anybody interested to learn more about Chicago”
Explore Chicago’s Underground *Pedway* with an expert guide, secret interiors, and art meaning clues near Millennium Park.
“Navigating through the Pedway isn’t as straightforward as it seems. Genuinely appreciate the insight the guide given us on this underrated utility as well as niche knowledge of the city’s history.”
Booze and Boos takes you through Lincoln Park pubs and ghost lore in about 2.5 hours with a costumed guide and drink stops.
“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.”
Chicago gangster food walk with Capone-style tunnel access, River North stories, and tastings of deep dish pizza, steak, and a Chicago hot dog.
“Our guide Taka was great. She made the tour an interesting and tasty experience”
A small-group Chicago walk mixing big-name art, iconic skyscrapers, and humor, ending at the Chicago Cultural Center.
“Colin is very personable and knowledgeable, even though he’s relatively young. He’s interested in art and will show you a bunch of cool things in the city. He’s also very adaptable when we started getting rained on and he just pivoted to underground walkways.”
Golden Age Chicago Loop architecture walk with a CAC-certified guide, Tiffany dome, Macy’s on State, and a glimpse inside Palmer House.
“Learned a lot about the history of Chicago and its buildings.”
From the river and the skyline to the gangster trails, the lakefront and the deep-dish counters, every way to spend a day in the city.
