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.
“Our Driver was awesome. Very friendly. Would definitely recommend him to anyone. The car we had was amazing nice comfortable ride”
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.
“pick up at airport was seamless. Driver was very polite and helpful, he was waiting for us at the airport. the vehicle was clean and comfortable. I will definitely use this service again.”
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 the absolute pleasure of touring the Art Institute of Chicago with Joe as our guide, and I honestly can't say enough about how incredible the experience was. His depth of knowledge was impressive, but what truly set him apart was his passion. It…”
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.
“Deen did a great job not only showing us the sites of Chicago but also Firehouse 51 (and we got a tour inside), the Fire Academy & Mollies, as well as many other sites used to file Chicago Fire. A great way to spend the…”
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.
“Driver Dana excellent. Communicated beautifully,, told us where to meet, was perfectly on time. Would use again for sure.”
Discover Chicago through a personalized 2-hour private walking tour. Customizable routes focus on art, architecture, food, and hidden gems with expert guides.
“Our guide Dave reached out prior to learn about what we wanted to do and see. He timely met us at our hotel and gave us a GREAT tour of downtown Chicago including lots of history, facts and places we had not considered including the…”
Discover Chicago with a private, customizable guided tour. Explore iconic sights, hidden gems, and enjoy local insights tailored to your interests.
“Sam best guide ever!!!”
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 awesome! It was my first time on a private sail with friends. We were comfortable, the sail was smooth and we had a great time. We didn’t want it 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.
“Driver on time and car very clean Polite and professional driver The drivers need to know that commercial cars DO NOT NEED car seats for kids, as per the Department of Chicago Police”
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.
“Deen was the best tour guide, very humble, jovial and very knowledgeable. He got stuck in traffic but not only informed us well in advance but also gave us more than extra time to visit places and made our day. We highly recommend Deen!”
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.