Skip the corny jokes and never-ending speeches — our shared tours are built for travelers who want the real Chicago, not a stand-up routine. ✔️ Over 20 iconic stops ✔️ Zero wasted time ✔️ Only the best views, landma... 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

This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognized for excellence by National Geographic, USA Today, The Associated Press, Cond... More

Taste fresh baked goods, Chicago Deep Dish, 'snappy' Chicago Hot Dogs, and more as you unravel a mystery! The Chicago Murder Mystery Food Tour is an interactive and tasty experience that combines history, game-play, and a delici... More

Feel the thrill of skydiving without jumping out of an airplane. It's true! Head to iFLY Chicago in Rosemont, a premier indoor skydiving facility powered by a state-of-the-art vertical wind tunnel. After a training session, you'll... 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

Voted the #1 Immersive Art Experience in America by USA Today readers in 2024, Color Factory Chicago celebrates the joy of color. Guests embark on a bright and colorful journey through 14+ immersive installations that inspire jo... More

Enjoy the Navy Pier Fireworks from the Chicago River. A brief version of Wendella's Lake Michigan Fireworks Cruise, this experience is 45 minutes and does not go out to Lake Michigan.... More

A helicopter tour of downtown Chicago is a unique and thrilling way to experience the Windy City. From high up in the sky, you'll be able to take in breathtaking panoramic views of Chicago's iconic skyline, world-famous landmarks,... More

Set sail for an exquisite evening of gourmet dining set to the backdrop of Navy Pier’s awe-inspiring fireworks show on our Fireworks Premier Plus Dinner Cruise on the Chicago River! A decadent plated dinner and craft cocktails w... More

I am the only person in the US, and possibly the world, that offers this experience. It is both a demonstration and an interactive opportunity where you'll have tons of fun learning about the history of cheese magic and getting to... More

Embark on the adventure of a lifetime! Step aboard the iconic California-Chicago Train Expedition as we whisk you away on a journey that combines the thrill of train travel with the magic of California's breathtaking scenery. From... More

Looking to experience something new? Great crafty event for date night, girl's night out, corporate events, or just plain ole solo. Learn step by step techniques to make your own 100% soy wax candles. Experience cultivating your ... 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

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS.  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, a 3-4... More

Fine dining and unrivaled skyline views await from the moment you step aboard our Premier Plus Chicago Lunch Cruise. A selection of delectable plated lunch specials and craft cocktails will delight your palate while captivating pa... More

The Frederick C. Robie House on the University of Chicago campus is considered one of the most important buildings in the history of American architecture. This Prairie style masterpiece is now a UNESCO World Heritage Site on the ... More

Chicago Air and Water Show 2025 Great for friends & family! PLEASE READ CAREFULLY Experience Chicago’s Air & Water Show from the Best Seat on the Lake! 10AM SAIL: Our first sail will depart at 10am sharp. Our first event wil... More

Leave the little ones at home and step into the shadows for a spine-chilling evening designed exclusively for adults. Not all spirits in Chicago are content to rest in peace—and not all hauntings are friendly. On our Wind & Sou... More

One of the most unique experiences in Chicago. Immerse yourself in the Roaring Twenties. Step back in time to Prohibition Chicago with da gangsters and da flappers, and your host, Vito Valentino. Great music, great food, great com... More