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“This was a very interesting and also funny tour! Our guide Tanner was amazing!!! We had a very good time”
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.
“This tour was great! We got to try all the most famous Chicago foods while learning all about the city. Jessika was an excellent guide. She told captivating stories and kept us entertained throughout! We had a great time!”
Join a historian-led Chicago South Loop tour blending gangster lore and ghost stories, with stops at Riverwalk, theatres, and haunted hotels.
“Oh my gosh, we absolutely loved our tour! Max was beyond amazing! As native Chicagoans looking for a Valentine’s Day to remember, this experience totally blew us away! It’s wild—we realized we knew so little about our own city that we actually felt like tourists in the best way possible. We learned so much cool…”
Deep-dish, hot dog, Italian beef and Chicago skyline stories on a small-group 4.5-hour walk with the Pedway and The Bean.
“Dave was extremely knowledgeable about Chicago. He gave excellent histories about various places and foods. I appreciated his candor and enthusiasm. The places he took us for food were solid and enjoyable. His ability to help us appreciate our surroundings was a pleasure. At times, his stories were sometimes complicated and difficult to follow -…”
Chicago Loop interiors and skyline views on a 2-hour walking tour with rare access to lobbies, domes, mosaics, and iconic landmarks.
“Ty was a wonderful guide, knowledgeable, engaging, funny. We thoroughly enjoyed the tour and learned a lot.”
Taste regional Chinese dumplings, noodles, Sichuan heat, and Portuguese egg tarts on a 3-hour Chinatown walk with landmark stops.
“This is a great tour of ChinaTown in Chicago. The food was delicious and we were stuffed! The tour guide Greg, was excellent. Plenty of breaks during the tour. Highly recommend this tour!!!!”
Chicago Loop secret interiors tour: $35, 2 hours from Union Station to iconic landmarks. Learn how light and structure shaped the city.
“this tour exceeded my expectations, Annie our guide was engaging, friendly, and very knowledgeable. we saw much more than I expected. it included outside architecture as well although I wish she had told us even more about the decorations, doorways, ETC that we were passing. however when prompted she was happy to discuss and was…”
Prohibition-era gangster stories meet Chicago food in 2 hours. Small-group walk with Harry Caray steak, deep-dish pizza, and dawgs.
“My husband booked a last minute tour and our guide Avery was great! He was so knowledgeable about the history of Chicago and we learned so much. It was so nice meeting new people and exploring a little! I highly reccomend this tour. The food we sampled was also excellent!”
Chicago Mobs and Haunts walking tour mixes Capone hangouts, haunted hotels, and ghost stories in the Loop for $34 in under 2 hours.
“Very enjoyable and informative tour. Bryson did a really good job. We particularly enjoyed the story at the Nederlander theatre.”
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.
“Adam was great! He knows everything about Chicago 😀”
Booze and Boos takes you through Lincoln Park pubs and ghost lore in about 2.5 hours with a costumed guide and drink stops.
“Seemed unorganized and the guide didn’t seem excited to tour. We left early because it seemed just like a bar-hop and not an informative walking tour. We wanted fun, engaging, and lively and both the guide and the other guests looked and seemed bored. We left early so we could bar-hop on our own.”
Chicago gangster food walk with Capone-style tunnel access, River North stories, and tastings of deep dish pizza, steak, and a Chicago hot dog.
“Allan did an amazing job on the WHOLE tour. Kept us informed and eager to go onto the next stop.”
A small-group Chicago walk mixing big-name art, iconic skyscrapers, and humor, ending at the Chicago Cultural Center.
“We were the only ones on our very hot, but super fun and interesting tour of downtown Chicago. It was an excellent, informative tour with lots of tidbits of history and photos that made everything memorable.”
Golden Age Chicago Loop architecture walk with a CAC-certified guide, Tiffany dome, Macy’s on State, and a glimpse inside Palmer House.
“The tour was very interesting and Ross was very knowledgeable with sharing so much information about the buildings and history of the times they were built. Anyone desiring more information on the history of Chicago and wanting to see many fascinating and beautiful buildings should go on this tour.”
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.
