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“Takes the guess work out of where to go, what to see by hitting the high points. Heath was great and I appreciated the insight about the works he shared with us.”
Chicago private custom city tour with hotel pickup. See Millennium Park, Loop, Lincoln Park, Hyde Park and Wrigley Field in 3–4 hours.
“Great experience. Ontime and vey punctual. No complaints about this Tour. My clients enjoy it to the max.”
Private door-to-door transfer from ORD or MDW to downtown Chicago in a chauffeur-driven sedan or SUV for up to 3.
“On time and clean transportation vehicle kind of quiet driver but good service. In addition, luggage assistance on pick up bd drop off.”
Semi-private Art Institute tour for up to 8 with skip-the-line entry, expert guide, and 2.5 hours of Impressionists and more.
“Our tour guide Joe shared detailed and interesting information about the art movements, the artists and how the museum acquired the different collections. He was excellent!”
Private 45-minute Chicago skyline helicopter tour from Schaumburg with headsets, photo-friendly flybys, and aerial views of The Bean to Navy Pier.
“Greatest experience ever the pilot was super nice and informative and made us feel safe. Very smooth flying good view amazing pilot 10/10.”
Private 2-hour downtown architecture walk from Chicago Theatre to Cloud Gate, with Pedway tunnels, river views, Picasso, and included snacks.
“Dash is very knowledgeable concerning the architecture in the various buildings it was apparent he enjoyed his job top notch tour”
Private chauffeur transfer from downtown Chicago to ORD or MDW with meet-and-assist, comfortable vehicles, and 24/7 service for small groups.
“The wonderful customer service of the drivers that picked me up at the airport and the hotel. Both drivers were friendly.”
A 2-hour private Art Institute tour with skip-the-line access, an expert guide, and major masterpieces tailored to your interests in Chicago.
“Information packed two hour tour of the institute with a very knowledgeable guide. A great way to see the museum”
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.
“We had an amazing time! Captain Mike took care of everything so we could just relax and enjoy the ride. I would definitely recommend this experience.”
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.
“I had expected a Suburban or Town Car, instead someone who drives for Lyft showed up. I could have saved $50 on my trip. Plus, I waited a good 45 minutes, that’s after I picked my bags up from the carrousel. Not what I was expecting. I have had car service from the airport in…”
Chicago’s skyline stories plus Chicago comfort-food tastings on a 5-hour private walk. Small group, lunch-style bites, easy transit.
“Our tour was good if your into architecture. A lot of walking so wear comfy shoes. Richard was very informative and if he didn't know something he made sure to find out. The food he took is to was ALL DELICIOUS! Overall good day.”
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.
“Leentje was terrific. So knowledgeable, well spoken, and so interesting. She was fun and accommodating (knew where the restrooms were!) made great suggestions for dining, and answered all our questions - really tailored our tour to our interests. I will definitely go on another tour with her.”
A private custom walking tour of Chicago with a local guide, flexible route, museum exteriors focus, and practical city advice for your day.
“El Guia tenia buena voluntad, pero falto de motivacion, iniciativa y conocimientos...esperabamos algo mas que un paseo con poco contenido de historia y anecdotas...”
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.
