Chicago · TOURS
265 tours
Good tours & days out fill up fast here, especially between June and the first hard freeze. These 15 are the strongest of them, with current prices and what separates one from the next.
Wendella’s 90-minute Chicago River architecture cruise with indoor warmth, big skyline views, and stories from 130+ years.
“The tour and tourguide were great! The time flew by and it was very interesting. If you have someone who needs the elevator to get to the dock, be sure to call the company for detailed instructions on how to get there. The staff was very helpful.”
Chicago Loop gangster tales and ghost stories on a 2-hour historian walk. Millennium Park, Palmer House, Riverwalk, and Capone legends.
“Very exotic experience, another good way to know about Chicago history beside just regular tourist spots”
Ride Chicago by coach on a crime-and-mob tour with comedy-bent storytelling, photo stops, and a mini mob museum for $49.
“Our host Dane was energetic and entertaining! We learned a lot on the tour and enjoyed the stops. Would recommend to those wanting to know more about Chicago history!”
A 45-minute Chicago River cruise with live architecture narration, flexible seating, and iconic skyline views from the Magnificent Mile.
“Very informative, interesting and exciting tour would highly recommend to all. Our guide was excellent. Sorry I could not find it out his name.”
A 90-minute Lake Michigan and Chicago River boat tour with live architecture narration and skyline views from Wendella dock.
“Very informative. Bring a small blanket- it was chilly. But if you’re hot, you could sit on the blanket. The chairs were pretty uncomfortable.”
Hop-on hop-off Chicago bus with open-top views, Wi-Fi, and 24, 48, or 72-hour passes to hit Millennium Park and more.
“It was really interesting and a great tiur.. The only reason I didn't give a 5 is because the bus was cold inside..No heat on a cold day”
A 3-hour food and walking loop through Chicago classics, Millennium Park sights, and downtown landmarks, plus a free bike or kayak bonus.
“We were combined with the Holiday food tour to make a group of 14 (Christmas Eve). Our guide, Fran, was personable and knowledgeable, and kept the group moving. My husband and I enjoyed the food and the stories--it was a great introduction to the city of Chicago.”
A 2-hour Chicago South Loop walk mixing Al Capone era stories and ghost legends, with stops at iconic landmarks and hotel interiors.
“Sophia was a delight! This was my favorite tour of this trip. So much knowledge and lore crammed into 2 hours. A must for true crime, history, and ghost story fans.”
See Chicago’s architecture up close on a 90-minute river cruise, with live narration, covered seating, and big skyline highlights for $37.
“Loved the view of the city. I’ve been to Chicago many times and this was the best experience to date.”
Step inside Chicago Loop interiors on a 2-hour guided walking tour. Art Deco spaces, stained glass, and mobile tickets for $35.
“Very fun tour guides, he was well educated about the city and knew a lot of minute details that you would miss out because you dont know what to look for. Excellent tour!”
Chicago Loop donut tasting walk with local stops, enough samples for a sweet meal, included history, and vegan and allergy options.
“Nick and Lauren were great! Loved going to all the different places. Family had a great time. Would highly recommend.”
See Chicago’s top sights from an open-top hop-on hop-off bus, with live tracking, digital commentary, and optional walking and boat tours.
“If you are an avid walker you could probably walk the entire loop of attractions this hop on, hop off does, but you’ll miss the entertaining and comical pre recording that plays as you get taken around. It differs to other tours I’ve done where there’s a guide on the bus talking, but maybe that was just the day I did it. It was a little rainy so I really enjoyed being driven around the loop, getting the fun facts and then picking where I’d like to go back to. I think a one day pass would be sufficient for most. I also thoroughly recommend downloading the big bus app…”
A small-group Chicago walking tour packing deep-dish, hot dog and Italian beef with Pedway, river views, and top architecture sights.
“The tour guide was very knowledgeable, super friendly, with a great Humor, making even an international guest feeling very comfortable. The tour was very interesting and I learned quite a lot about Chicago and the Chicago food.”
Chicago Loop food tour with deep-dish, Italian beef, hot dogs, sweet bites, and architecture stops, ending at Millennium Park.
“Mike was a great tour guide and the food was amazing. The route is great because it offers such a historical lesson.”
90 minutes on a comfy Chicago mob bus. See the St. Valentine’s Massacre site, Dillinger steps, Frank Nitti artifacts, tunnels, and a quiz.
“Great tour with lots if interesting fact. If you like the mob you’ll enjoy the tour”
