Chicago · CITY TOURS
44 tours
One day in Chicago and you want the whole grid: these are the tours that manage it. Minibus loops, combined boat and bus tickets, hop-on services along Michigan Avenue, with routes, running times and prices for each.
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.”
Minibus tour of downtown Chicago plus an optional 75-minute open-top River Architecture Cruise, with expert narration and prime skyline views.
“Avery was our guide and he was great. Very good knowledge of the city and the communication was excellent.”
Feel the rush on a Seadog speedboat from Navy Pier, cruising Chicago’s skyline with a live guide, and add Extreme 360 spins.
“It was very windy and loud, but our 2 and 4 year old enjoyed the boat ride. Thirty minutes was the perfect amount of time.”
A 2-hour Chicago minibus tour with live narration, a small group, four photo stops, and skyline views from key landmarks.
“Avery was amazing—hands down one of the best tour guides we’ve had! His knowledge of Chicago history was impressive, and the way he told the city’s stories made every moment captivating. Chicago truly came alive through his storytelling.”
City Cruises Chicago Signature Lunch Cruise on Lake Michigan: a small-group 2-hour ride from Navy Pier with buffet lunch, DJ, skyline views.
“When I say we had a time last night that’s what I mean it was 16 of us and when I say Danny the event host was AMAZING. I would recommend this event to anyone for any occasion. We were on the Spirit of Navy Pier.”
City Cruises Chicago Odyssey lunch or dinner cruise with a 3-course plated meal, 360 skyline views, and live DJ music.
“Loved the salad and desert. The chicken dinner was okay”
75-minute Seadog speedboat architecture cruise from Navy Pier, through Chicago Harbor Locks, ending with Lake Michigan skyline speed views.
“I took the tour of a day that happened to be really foggy. According to the tour guide, Andy, it was very unusual. I was in Chicago for a few days whole my husband went to a tech conference there. Several people recommended I take an architectural boat tour. I'm so glad I did and honestly, this company was a great choice. The speedboat helped keep me from getting sick (just a little during the river lock transitions). Our guide Andy was very knowledgeable and quite funny. I would've loved for it to be longer. Also, my husband was surprised when I told him I considered going again later in…”
Bike Chicago's lakefront, Museum Campus, and Grant Park in 3 hours, led by friendly guides with all bikes and helmets.
“Dan was great! He safely guided us through the Chicago masses as the triathlon was happening and provided an overall amazing experience. We went to all the major spots downtown and he showed us amazing views of the city’s skyline! Was also super informative as he talked about the architecture, the Chicago flag and lots more of Chicago's history! 100% recommend to anyone visiting!”
Two hours of buffet brunch, DJ music, and skyline views from Navy Pier on Lake Michigan, with optional bottomless mimosas.
“Note: Meeting place is at the pier where your boat is docked not in Navy pier address (entrance). All in all it was an excellent activity. The staff was excellent!”
Private 3-4 hour Chicago drive with hotel pickup. See Millennium Park, The Loop, Lincoln Park, Hyde Park, and Wrigley Field.
“The bean and Wrigley field. Buying cub jerseys personalized. The skyscraper view at navy pier. Chicago university.”
Chicago in comfort with a guided minibus tour, photo stops, and optional 75-minute Architecture Cruise along all three branches.
“Our guide, Rick, was informative and had interesting facts/stories and some funny remarks along with way. I would highly recommend this tour.”
2-hour Chicago River brunch, lunch, or dinner cruise with skyline views, chef-prepared courses, narration, and possible Navy Pier fireworks.
“The best good and service on a lunch cruise. The European style river craft was great! Views all around and up!!!”
Lincoln Park ghost stories, asylum legends, and Tudor pub chills on a small-group 1-hour Chicago walk. Mobile ticket, $32.
“I highly recommend this ghost tour— Elliot was an incredible tour guide! We were a bigger group, but he ensured that the atmosphere was still spooky and no information was missed. He is a superb storyteller. My husband and I opted for the extended tour and it was absolutely worth it. We just moved to the area and have been scoping out touristy activities to bring our friends on when they visit. We will definitely be back!”
A 2-hour Chicago Loop food tour with hot dog, deep-dish slice, and Italian beef, plus Riverwalk and landmark sights.
“It was such a fun experience to hear about Chicago architecture mixed with food! We loved the pizza and donuts especially! Dave does many tours so we look forward to using him again when we head back to Chicago!!!”
Private 2-hour walking tour of Chicago architecture highlights, including Riverwalk and Cloud Gate, with snacks and a train pass.
“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.”
