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“Really cool tour. Todd knew about pretty much everything we drove by (which TJ was making sure was as smooth and comfortable as possible). Options were given and our interests were considered. We'd been to Chicago several times, but all we saw and heard about…”
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.
“Smooth and seamless transportation from beginning to end. Drivers were on time at pickup and drop offs.”
Experience Chicago from above with this private 45-minute helicopter tour, offering stunning skyline views, key landmarks, and personalized service.
“It was my wife's 81 birthday gift from me. She absolutely loved every minute of the trip around Chicago and the lake front. We also got to see Wrigley Field from the air. My grandson also accompanied us on the trip. It was special to…”
Enjoy a hassle-free, private transfer from downtown Chicago to O'Hare or Midway airports. Comfortable, reliable, and tailored to your schedule.
“On time pick up in a clean and comfortable vehicle, a friendly and helpful driver! Art is an excellent employee and an asset for your company.”
Discover the art masterpieces of Chicago with a private, expert-guided tour at the Art Institute, including skip-the-line access and tailored insights.
“Heath has a fascinating and novel perspective as a former art dealer he gave us a whirlwind tour of 500 years of art and the influences driving developments”
Experience Chicago from Lake Michigan on a private sailing trip. Enjoy stunning skyline views, customizable routes, and expert guidance—all in an intimate setting.
“Lovely morning sail on Lake Michigan with the skillful, personable and knowledgeable Captain Ulysses!”
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.
“My wife and I were in Chicago for the marathon and booked the tour for a few days after. Deen kept us well updated both the day before and, on the day, even when delayed in the Chicago traffic but he didn’t cut the tour…”
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.
“The driver was so nice and was so helpful. Was on time and focus on driving us to our hotel destination.”
Discover Chicago through a personalized 2-hour private walking tour. Customizable routes focus on art, architecture, food, and hidden gems with expert guides.
“Leentje was so friendly, knowledgeable and provided us with such a wonderful tour. I would definitely recommend her to others.”
Discover Chicago with a private, customizable guided tour. Explore iconic sights, hidden gems, and enjoy local insights tailored to your interests.
“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...”
Experience Chicago from Lake Michigan with a private sunset sail. Enjoy customizable routes, stunning skyline views, and personalized service for up to 6 guests.
“A fantastic experience - beautiful weather and relaxing atmosphere. Will definitely try again and recommend to others”
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.
“This is a great tour! The guide, Deen, is very friendly and flexible in arranging things based on our interests and needs. We are happy to see various places and take great pictures of Chicago during our brief stay here.”
Efficient and comfortable one-way private transfer from Midway Airport to Chicago hotels. Perfect for hassle-free arrivals in a luxury vehicle.
“Our driver was very prompt. The driver was so nice and the car was spotless. Very easy to locate. Dropped us off at the perfect location.”
The river runs through an architecture lesson, and the lake applauds.