Chicago · TOURS
Anything with a guide, a boat or a bus attached, in one list. The 15 below are the ones worth giving a whole afternoon, priced and paced, with the rest of the catalogue below them.
Cruise all three branches of the Chicago River, hear lively architecture stories, and see icons including Marina City and the Wrigley Building.
“Well worth the trip. Learned so much about Chicago and the stories behind its architecture. We definitely recommend this during your trip.”
Explore Chicago’s Loop through true gangster tales, Al Capone sites, haunted hotels, and ghost stories on a lively two-hour walking tour.
“It was a very cold, windy Chicago night but the tour guide braved it out so we did too--and so glad we did! It was interesting listening to all of the stories about Chicago while wallking around the streets at night. We really enjoyed the tour but will never swim in the water in and around Chicago! Lol”
Explore Chicago’s mob past by coach, with Al Capone sites, the Biograph Theatre, St. Valentine’s Day Massacre site, and Nitti’s vault.
“Great tour guide! Windows of bus were fogged, couldn’t see anything but stories were great! Good length but they need to fix the windows in winter with fogging!”
Cruise Chicago’s river for 45 minutes of architecture, live stories, skyline views, indoor shelter, and a smart $28 price.
“The tour was great cold 🥶 but great. Tour was funny and knowledgeable. I would recommend in the warmer months.”
Cruise Chicago’s river and lakefront for 90 minutes of architecture, skyline views, live stories, indoor seating, and practical tips for $45.
“A lot of information in a short time. The guide talked very fast. People were standing blocking the view”
See Chicago’s top sights from an open-top double-decker bus, with flexible 24, 48, or 72-hour passes and live tracking.
“Easy way to get around and see the city. The app gives you a general idea where the buses are so you can time your stops and reboarding.”
Taste Chicago classics, see Loop landmarks, and learn local stories on a three-hour food walk with a free bike or kayak rental.
“This is tough! Our tour guide Fran was absolutely amazing and had great energy, but I’m not sure I would recommend this food tour. My family and I did the Architecture Boat Tour the day before and this shared the same concept- they both had the same exact information, so that became very repetitive. The food itself was also OK. Nothing amazing or worth wild so we were all a bit disappointed because a lot of the reviews said, it’s the best!”
Explore Chicago’s gangster past and ghost lore on a historian-led South Loop walk through Death Alley, the Riverwalk, and haunted hotels.
“Sophia was very informative and very friendly! Was a last minute book and we enjoyed it, especially the Palmer brownie!”
Cruise all three branches of the Chicago River, hear lively architecture stories, and see landmarks from an open-air or covered boat.
“Learned a lot, the weather was prefect, and our guide provided great info about the city. The sunset with views was 🤩.Definitely would take this tour again.”
Explore Chicago’s dazzling Loop interiors, Art Deco details, and stained glass with a local guide on this smart 2-hour walking tour.
“Out tour guide is Heath. I think he is great at explaining things and he has abundant knowledge of architecture. I really enjoyed his interpretation along the way and it made the tour very enjoyable. If you’re not a local, it’s hard to find these places yourself. In my opinion the tour is really worth it if you stay in Chicago and want to explore things less touristy.”
Sample Chicago donuts, hear local stories, and see Loop landmarks on a two-hour walking tour with vegan and allergy-friendly options.
“This is my favorite tour! I’ve booked it 3 times in the past year and brought new people. It’s always a hit and everyone’s favorite. Aside from the amazing Chicago doughnuts, you get a history of the shops and some of the local building’s you pass on the way. I particularly like that history is more personal and includes nuanced stories that you don’t hear on other tours. I’ve had the same guide all 3 times, Nick, and he is GREAT. He’s funny, personable and makes a point to talk with everyone in the group as we walk around. I highly recommend this tour.”
See Chicago’s skyline, parks, museums, and lakefront by open-top bus, with flexible hop-on stops, digital commentary, and optional boat cruise.
“Felicia was awesome! She was very informative with history and fun facts. Very professional and pleasant to listen to her! She’s the best!”
Taste deep-dish pizza, hot dogs, Italian beef, and Chicago architecture on a small-group walking tour of the Loop and River North.
“David was an awesome guide of the city. Chicago is an amazing town and we learned so much. The food and architecture is top-notch. We had a great time and our group was fun!”
Taste deep dish, Italian beef, hot dogs, and more while exploring Chicago’s Loop landmarks on a three-hour small-group food walk.
“Eliot was awesome! She showed up some beautiful buildings and chatted about history while we did our food tour. She was absolutely hilarious and had lots of cool facts about downtown. The food was excellent and very healthy portions so you get a good bit of food. Definitely recommend”
Explore Chicago mob history by bus, from the St. Valentine’s Day Massacre site to Dillinger’s final steps, with live stories and crime artifacts.
“Jay was a great tour guide! Really informative! Really enjoyed the tour!! The bus was quite loud and squeaky and it was hard to hear even with her speaker on full volume!”
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