Indulge in a VIP dinner experience at Chicago’s Skydeck, offering breathtaking views from 1,353 feet (412 meters) above the city. Located in the iconic Willis Tower, this exclusive experience lets you enjoy the stunning skyline ... More

Experience the ultimate in comfort, reliability, and professionalism with our premium black car service in Chicago and surrounding areas. We specialize in private transportation for business and leisure travelers, offering: • ... More

Five days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the United States, all of which are located in Lake Michigan in the United States, Lake Superior, the largest freshwater lake in the wo... More

Visit the birthplace of a truly American architecture. Wright’s Oak Park Home and Studio served as both residence and workplace for the first 20 years of architect Frank Lloyd Wright's career. See how he tried out innovative des... More

The contrasts between urban and rural Jamaica will surprise you during this tour of Kingston and the Blue Mountains. Among the star attractions are visits to a coffee plantation, Emancipation Park and the Bob Marley Museum.... More

The Offbeat Street Art Tour is the first tour in Chicago that truly celebrates Chicago's street art scene. No other tour takes guests out into the streets to showcase and highlight the vibrant street art scene which many people ov... More

Looking for fun things to do in Chicago? Look no further! Join one of our professional guides on a scenic 6-8 mile Chicago Segway tour. Glide effortlessly through the fragrant garden paths of Grant Park to marvel at the iconic Buc... More

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More

This tour is unique as it offers the ability for you and two of your friends or family (a total of 3 passengers) to experience what it is like to fly over the city of Chicago on a 45 minute thrill seeking guided tour. The price is... More

The Windy City is known for its food, architecture, and haunting history! Walk with us as the sun sets through downtown Chicago, hearing some of the most gruesome and creepy Chicago stories. The first stop is the Congress Hotel, t... More

Let our expert local guides share their passion with you for The Art Institute of Chicago on this private 2 hour tour. As you traverse the hallowed halls, you’ll discover an extraordinary collection spanning centuries and cultur... More

Immerse yourself in Chicago's architectural heritage on an exclusive walking tour, delving into the city's iconic structures and Art Deco gems. Begin your intimate journey by marveling at the grandeur of the Wrigley Building, foll... More

Embark on a profound, downtown walk-around, to discover incredible stories and secrets of the city on this not to miss feet on the street experience! During our loop around "Da Loop" we will peel back the layers of this Great Big ... More

This tour is perfect for the entire family, put on by Bobby’s Bike Hike, whose food tours in just the past year have ranked as Top 10 in America by USA Today and Top 20 in the world by Tripadvisor. Biking is easy in Chicago beca... More

Come on our chilling ghost tour presented by US Ghost Adventures! Book Directly With Windy City Ghosts and save $5/person. Windy City Ghosts walking Ghost Tour provides a look into the darkness that lurks below Chicago’s busy st... More

Sunday Funday Mimosa Cruise – Chicago’s Floating Tiki Bar Adventure! Sundays are Fun-Days aboard our vibrant floating tiki bar, Island TIme, where the drinks are cold, the vibes are high, and the views are iconic! Cruise down... More

Step into the world of America's best musicians, comedians, and superstars with the Chicago Theatre Tour Experience. Embark on a captivating journey from the theatre's inception in 1921 to its present-day status as a premier enter... More

Enjoy convenient private transportation between Midway or O'Hare International Airport and your hotel in the comfort of a private 14 Passenger. Mercedes Sprinter Executive Van. Thank you for choosing us. If you have more than 14 c... More

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 10 PASSENGERS TOTAL.  Thank you for contacting Chicago Private Tours! We would love to help your group discover Chicago.  Our services include pick up from your downtown Chicago hotel... More

Flytographer Private Vacation Photo Shoot Connect with a local hand-picked professional photographer in Chicago and capture your most memorable moments during this private photo shoot. Get insider tips on the best things to do in... More