Chicago · PRIVATE
Every trip has one free afternoon too few. These 15 private tours justify the slot, priced and timed so you can decide in minutes and get back to the fun part of planning.
A private, skip-the-line guided tour of the Art Institute of Chicago, covering major works and stories in 2.5 hours.
“Samantha was knowledgeable, quite insightful, and animated just enough to keep our attention and desire to learn focused.”
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!!!”
Private Chicago airport arrival transfer from ORD or MDW to downtown, with door-to-door service, chauffeur meet-and-greet, and sedan or SUV options.
“James was great, made the experience seemless. Great service. Would recommend to family and friends.”
Semi-private skip-the-line tour of the Art Institute of Chicago. 2.5 hours, admission included, max eight, and expert-led highlights.
“Samantha's knowledge, personality, professionalism and enthusiasm while touring is priceles. She provided education and entertainment while giving undivided attention. Overall an outstanding experience.”
A private 45-minute helicopter flight over Chicago’s skyline, stadiums, parks, and iconic views, with headsets included for easy, scenic photos.
“My flight was canceled and never rescheduled. I never received a refund. No one ever contacted me back to reschedule or offer a refund.”
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.”
Private hotel-to-airport transfer in Chicago, door-to-terminal drop-off, chauffeur help, and 24/7 service to ORD or MDW.
“Our driver was on time, friendly and helpful. HOWEVER, I reserved a SUV and received a minivan. Confirmation was made early morning Mon/Apr24 and yet received another one at 10:45pm. He made mention of late call and a minivan would be there AND I noted I reserved and confirmed a SUV”
Private 2-hour Art Institute of Chicago tour with skip-the-line entry, expert guide, and major works, plus time to explore more after.
“Marlin was an excellent guide with flexibility for our interests guiding us through the art museum tour with authenticity, highlights, and fun.”
Private 2-hour sail on Lake Michigan from Navy Pier. Flex route, Bluetooth music, and Chicago skyline views for up to six.
“Captain Mike was awesome, really friendly, making the trip truly memorable. The city of Chicago is the perfect backdrop, so we absolutely recommend!”
Private 3-hour Chicago food tour with deep dish, Italian beef, hot dog, sweets, and Loop architecture walks that make lunch feel meaningful.
“Need to walk and be hungry. This was an awesome combination of history of Chicago food but all history.”
Private MDW to downtown transfer with flight-aware pickup, air-conditioned vehicle, and simple voucher-based meet-up to skip taxi stress.
“It was HORRIBLE….please see pictures! The company sent a very unfriendly man who was dressed like he just got out of bed. His personal MINIVAN reaped with cigarette smoke. The minivan was FILTHY to say the lease! I’m requesting a refund and will fight to the end to get it!!! DO NOT USE THIS COMPANY!! Oh, trying to call and /or talk to the company is almost impossible. A BIG waste of $90!!”
Small-group Chicago architecture and food walk. Capped at 12, big tastings, Willis and Water Tower views, plus a guide who brings it to life.
“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.”
Private ORD to Chicago hotel transfer with a flight-tracked driver, air-conditioned car, and luggage help, priced from $40 per person.
“Thank you for great service! The drive to my hotel was smooth! A great start for my first time in Chicago!”
A private 2-hour walking tour in Chicago tailored to your interests, covering Millennium Park public art like The Bean and Cloud Gate.
“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, customizable Chicago walking tour with a local guide, tailored sights, optional museum time, and practical insider tips in your language.
“Service sublime notre guide Bart nous a bien expliqué l’histoire de Chicago le tout dans un français parfait :) une visite à faire on aurait du prendre davantage de temps que 2h je recommande vivement cette visite en français de l’histoire de Chicago”
Every kind of day out in the city, and the best of each.
