Chicago
The private bookings: architecture mornings, food crawls and city days set to your pace. The custom routing earns its keep in winter, when outdoor time wants rationing.
Discover Chicago’s highlights on a personalized 3-4 hour private tour. Enjoy hotel pickup, expert guides, and flexible stops to see the Windy City's best.
Most Popular“The knowledge of Mike was simply outstanding !! TJ and Mike are a great team , my wife and I had plenty of laughs but also we learnt so much about the history of the city.”
Book this private Chicago airport transfer for a stress-free ride in luxury to downtown hotels. Perfect for travelers valuing comfort, reliability, and hassle-free arrivals.
“James was great, made the experience seemless. Great service. Would recommend to family and friends.”
Experience Chicago from above with this private 45-minute helicopter tour, offering stunning skyline views, key landmarks, and personalized service.
“It was an amazing time…..even if your scared of heights I highly recommend you still go, won’t regret it.”
Enjoy a hassle-free, private transfer from downtown Chicago to O'Hare or Midway airports. Comfortable, reliable, and tailored to your schedule.
“On time, polite. Helpful with baggage. Friendly. Was professional. Good communication through text and email.”
Discover the art masterpieces of Chicago with a private, expert-guided tour at the Art Institute, including skip-the-line access and tailored insights.
“We had a great time with Joe! He showed us not only some of the highlights of the museum, but also told us the incredible stories behind them. We were a family of 4, with myself, my husband, our 17 year old and our 10…”
Experience Chicago from Lake Michigan on a private sailing trip. Enjoy stunning skyline views, customizable routes, and expert guidance—all in an intimate setting.
“We 5 ladies enjoyed a beautiful afternoon sailing! The boat was clean and comfortable. Captain Mike was knowledgeable and friendly. The afternoon was perfect!”
Discover Chicago Fire filming locations on this private tour, visiting iconic sites like Molly's Pub, Firehouse 51, Millennium Park, and more—perfect for fans.
“This is an amazing tour-a must for Chicago Fire fans! Dean is a great tour guide. He showed us several spots where they film the show including Molly's and was able to get us into the firehouse. He also drove us to highlight spots of…”
Discover Chicago’s top eats and architecture on a private 3-hour walking tour, sampling iconic foods and exploring the city's vibrant Loop district.
“Need to walk and be hungry. This was an awesome combination of history of Chicago food but all history.”
Stress-free private transfer from Chicago Midway Airport to downtown for $50. Enjoy air-conditioned comfort and personalized service—ideal after flights.
“OUR driver (Jason, I think) contacted me immediately upon booking. The day of arrival he was exactly where he said he’d be at exactly the time he said he would be there. His car was immaculate and very comfortable (Tesla). I’m hoping we get the…”
Discover Chicago through a personalized 2-hour private walking tour. Customizable routes focus on art, architecture, food, and hidden gems with expert guides.
“Great tour! Very personalized and the guide Mimi was very knowledgeable and informative! Highly recommended!”
Discover Chicago with a private, customizable guided tour. Explore iconic sights, hidden gems, and enjoy local insights tailored to your interests.
“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”
Experience Chicago from Lake Michigan with a private sunset sail. Enjoy customizable routes, stunning skyline views, and personalized service for up to 6 guests.
“Mike was a great guide and very friendly!! Nice boat, pretty ride and would 100% book this again. Highly recommend.”
Seamless, private transfer from O'Hare to downtown Chicago in a comfortable SUV. Perfect for stress-free arrivals, with personalized service and upfront pricing.
“Excellent service, on time, clean, very professional driver and safe. Very pleased. Will be using the service again.”
Discover Chicago's top sights on a private 2-hour scenic driving tour, including Wrigley Field, Millennium Park, and stunning lake views—perfect for quick, personalized sightseeing.
“Careful driver, friendly. Took us to all the best sites in Chicago, got some great pictures and memories from our trip here.”
Efficient and comfortable one-way private transfer from Midway Airport to Chicago hotels. Perfect for hassle-free arrivals in a luxury vehicle.
“The driver was fantastic! So friendly and professional. The car was clean and luxurious. Definitely recommend”
The river runs through an architecture lesson, and the lake applauds.