CHICAGO · ILLINOIS
The best of Chicago.
The 15 best private 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.
Private Art Institute of Chicago skip-the-line guided tour with an expert guide, smart pacing, and a 2.5-hour route through major works.
Most Popular“This tour, especially if you request and get Spiro as your guide, is so good that it is worth making the trip to Chicago for this alone.”
Chicago private custom city tour with hotel pickup. See Millennium Park, Loop, Lincoln Park, Hyde Park and Wrigley Field in 3–4 hours.
“Todd was great. We got on well and he was very patient with my son who is on the spectrum. We learned a lot, enjoyed the stops and saw things that even my kids were impressed by. I would recommend this service to anyone wanting a tour of Chicago.”
Private door-to-door transfer from ORD or MDW to downtown Chicago in a chauffeur-driven sedan or SUV for up to 3.
“Prompt pick up at the airport even though flight was 30 minutes early. Very friendly and personable.”
Semi-private Art Institute tour for up to 8 with skip-the-line entry, expert guide, and 2.5 hours of Impressionists and more.
“Ben was a great guide and we had a wonderful time. He took us to different areas of the museum and really explained the paintings well.”
Private 45-minute Chicago skyline helicopter tour from Schaumburg with headsets, photo-friendly flybys, and aerial views of The Bean to Navy Pier.
“1 of 1 experience! Hospitality from when we arrived all the way until we got off the helicopter was nothing less than stellar. Our tour guide was super informational, soft spoken guy but really put us at ease as it was our first time!”
Private 2-hour downtown architecture walk from Chicago Theatre to Cloud Gate, with Pedway tunnels, river views, Picasso, and included snacks.
“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.”
Private chauffeur transfer from downtown Chicago to ORD or MDW with meet-and-assist, comfortable vehicles, and 24/7 service for small groups.
“driver never showed up and company still wanted to charge me and refuse to give me a refund. when i contacted the driver he said he called and since i didn't answer, he didn't come. the number he called from was from a female name that i didn't recognize and don't answer unfamiliar numbers”
A 2-hour private Art Institute tour with skip-the-line access, an expert guide, and major masterpieces tailored to your interests in Chicago.
“Joe was an amazing guide. Informative and very interesting! Explained the history of the artist as well as the painting.”
Private sailing on Lake Michigan from Navy Pier lets you cruise past Chicago’s icons in a flexible 2-hour charter for up to six.
“It was a great chance to kick off the fall with a sailing trip with friends. Captain Mike was a great captain and host - we asked hundreds of questions and learned a little bit about sailing and a whole host of other related topics. The Bernard was perfect for six - and we had…”
Private 3-hour Chicago Loop food tour with deep dish, Italian beef, a hot dog, and architecture stops near Millennium Park.
“Need to walk and be hungry. This was an awesome combination of history of Chicago food but all history.”
Private transfer from Chicago Midway (MDW) to downtown with flight-time tracking, professional drivers, and air-conditioned rides.
“Driver was on time, communicated in advance and was conscientious. Pleasant, professional, and caring.”
Chicago’s skyline stories plus Chicago comfort-food tastings on a 5-hour private walk. Small group, lunch-style bites, easy transit.
“Chi-Tall Dave is an amazing tour guide. He gave us insight on Chicago then and now. The food stops were delicious and architecture locations were beautiful. Worth it and can’t wait to come back and try all these stops with family and more friends.”
ORD to Chicago hotels in a one-way private ride with flight tracking, air-conditioning, and luggage help for a smooth arrival.
“Thank you for great service! The drive to my hotel was smooth! A great start for my first time in Chicago!”
A 2-hour private Chicago walking tour customized to your interests, covering Millennium Park icons and public art, with free admissions.
“Our guide Dave reached out prior to learn about what we wanted to do and see. He timely met us at our hotel and gave us a GREAT tour of downtown Chicago including lots of history, facts and places we had not considered including the Read more”
A private custom walking tour of Chicago with a local guide, flexible route, museum exteriors focus, and practical city advice for your day.
“Visite irrégulière en intérêt..”
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.
