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“Our tour was enjoyable & entertaining. Excellent knowledge of the city & made it so much better by stopping by the site to chat about it before moving on to the next landmark.”
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.
“Great driver & pick up. Would use them again. Clean vehicle & friendly. Being on time is what matters. :)”
Experience Chicago from above with this private 45-minute helicopter tour, offering stunning skyline views, key landmarks, and personalized service.
“The pilot was awesome and had great tour comments. We were about to fly really close to the buildings in downtown Chicago, over Lake Michigan, by the river and west Chicago!”
Enjoy a hassle-free, private transfer from downtown Chicago to O'Hare or Midway airports. Comfortable, reliable, and tailored to your schedule.
“Great driver from downtown Chicago hotel to airport! Very nice and on time. Helpful with luggage! Highly recommend!”
Discover the art masterpieces of Chicago with a private, expert-guided tour at the Art Institute, including skip-the-line access and tailored insights.
“Best way to experience the Art Institute of Chicago. So much to see and do, it’s always best to rely on an expert. Joel provided us with all the highlights, including the behind the scenes insights like how the piece was acquired. That allows you…”
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.
“It was a very good experience for me and my family. Deen was great with us. I really suggest this tour. We really enjoy”
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.
“Friendly driver. Efficient. Arrived in good time. Clean vehicle. Stress less drive. Good communication about arrival”
Discover Chicago through a personalized 2-hour private walking tour. Customizable routes focus on art, architecture, food, and hidden gems with expert guides.
“First time in Chicago and our excellent tour guide Dave managed to make us discover most of the downtown sightseeing and some hidden gems while explaining the stories and history being them. Very informative and very pleasant experience!”
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.
“The captain was ready for us when we arrived. He was very informative. Great experience from beginning to end!”
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.
“Very pleased with their friendly & excellent service vMade our arrival very easy & positive highly recommend”
The river runs through an architecture lesson, and the lake applauds.