Chicago · CITY TOURS
Every trip has one free afternoon too few. These 15 city tours justify the slot, priced and timed so you can decide in minutes and get back to the fun part of planning.
Chicago Loop donut walk with 5 stops, enough tastings for a sweet meal, local stories, and vegan options on request, $70 for about 2 hours.
“This tour was FANTASTIC! The guides were extremely engaging, and you learn as much about Chicago as you do about the donuts!”
See Chicago fast by minibus, then upgrade to a Chicago River architecture cruise. Expert guides, skyline stops, strong value.
“Great tour guide, very knowledgeable and fun. Small bus was clean and comfortable. It was very cold in January so this was a great way to see the city and highlights and get some good insight to places you may overlook.”
Ride the Seadog speedboat from Navy Pier for a guided Lake Michigan skyline tour, with an Extreme Thrill upgrade for 360 spins.
“This ride was great fun! Captain Swag was amazing. Be prepared to get soaked!”
A 2-hour small-group minibus tour for Chicago highlights, photo stops, and live narration, with flexible views of The Bean and the skyline.
“Great tour! Avery is an expert and showed us all around! All well organised and so enlightening. Thanks Avery!”
City Cruises Chicago lunch cruise on Lake Michigan with skyline views, small-group vibe, chef-prepared buffet, and DJ entertainment.
“It was not clear exactly where the ship was. I only saw 600 E Grand Avenue, we were at the pier at 11:45 for a 12:30 sailing. It took us 44 minutes to find the boat. We got there at 12:29 and just made it. I would have been extremely angry if I lost over $500.00 had we missed it. We are from PA and not familiar with the area. 600 E Grand is the address for the shopping mall and ithe information desk could not help us. The food was fine, music a little loud. Staff very friendly”
3-course lunch or dinner on Chicago’s Lake Michigan with 360 skyline views, a live DJ, and time on deck. From $88.
“Everything was excellent except the music was way too loud. Also the children on the boat took over the dance floor by chasing each other and doing cartwheels and back flips. Later one little girl began screaming and enjoyed it so much she continued to scream for the next almost thirty minutes. Her mother ignored it and no staff member asked her to stop or spoke to her mother. It almost ruined our birthday party because we couldn’t converse. The food was excellent as was the service. We had lovely weather. The bathrooms were very clean.”
A 75-minute Seadog speedboat ride from Navy Pier with live architecture narration, Chicago River locks, and a fast Lake Michigan finale.
“Very fun tour. I will definitely recommend the tour to anyone visiting Chicago”
A 3-hour Chicago bike tour from the Lakefront Trail to Millennium Park, plus Museum Campus stops. Bikes and helmet included for $59.
“Great ride! Would do it again! Better than a boat tour! We both enjoyed it and learned a lot! They even had a trainee who was on her second day but was super knowledgeable as well!”
2-hour Lake Michigan lunch or dinner cruise from Navy Pier with skyline views, buffet dining, DJ fun, and rooftop games.
“Omg, this was amazing. The food and service was wonderful!!!!!! We'll be going again.”
Private Chicago city tour with hotel pickup, guided stops at Millennium Park, Lincoln Park, UChicago, Wrigley Field, and the Loop.
“Everything we wanted and more. Our expectations were exceeded. I would highly recommend this tour with TJ and our tour guide!!!”
Climate-controlled minibus tour of Chicago’s top sights, with photo stops and expert English narration, plus an optional 75-minute architecture cruise.
“I think the whole was greater than the sum of the parts. The minibus was good, the boat tour was good, but the two together were great!”
Glass-walled Chicago River dining cruise with 3-course meal and skyline views. Brunch mimosas, dinner DJ, sometimes Navy Pier fireworks.
“We sailed around the city, and was introduced to the Chicago skyline, and architecture.”
Lincoln Park ghost walk in Chicago with researched stories and outdoor stops, small groups up to 15, and a mobile ticket.
“I felt the size of this tour was too large for everyone to easily hear and interact with the guide. The “ghost stories” weren’t very compelling or interesting. Perhaps it could have been livened up with embellishments. Everything was told to us very factually. I will caveat my comments about the tour size by acknowledging we went Halloween weekend so it might be less crowded other times of year and we saw other tours that were similar, if not larger in size so perhaps it’s just customary for these tour groups to take on insanely large groups and the expense of being able to interact and hear all the stories…”
A 2-hour Chicago food tour with classic tastings, Riverwalk and Loop sights, and friendly English guides in a small group.
“Dash was terrific! The tour itself was good, but what made it exceptional, was him. He has and SO much knowledge about the city, great stories, tons of history-those are the things that made the tour so great!”
2-hour private Chicago architecture walk: Chicago Theatre neon, Pedway tunnels, Riverwalk views, Wrigley, Tribune, and Millennium Park.
“Never would have known to "look up" at Macy's. We also went back to the Walnut Room for Mrs. Hering's chicken pot pie.”
Every kind of day out in the city, and the best of each.
