This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to the overall narrative of Chicago. On this tour, we will explore the famous and mys... More

Get acquainted with Chicago’s most iconic landmarks on this riotous guided bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-running city bicycle tour company, on this exciting and informative adve... More

This tour is just a short walk through great Chicago neighborhoods starting near Navy Pier and the Magnificent Mile, and then heading into the Gold Coast & River North. Compare two American pizzas vs. two Italian pizzas to underst... 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

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

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

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

Looking for fun things to do in Chicago? Explore the city with one of our professional guides on a scenic 6-7 mile tour. Begin your adventure by gliding through the fragrant garden paths of Grant Park, where you'll admire the icon... 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

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

Explore Chicago’s amazing architecture from the unique perspective of elevated trains and station platforms. Learn the history behind the famous "L" system and hear how it has shaped the development of buildings within the Loop.... 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

Immerse yourself in Chicago’s distinct skyline with bold skyscrapers and incredible views of Lake Michigan .Enjoy the efficiency of having your own local expert and personal guide to share unique and fascinating stories about th... 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

Take a detour off the beaten path, and explore the flavors of Chicago’s vibrant West Side with Bobbys's Bike Hike, America's longest running city bike tour company, who recently ranked as Top 20 Food Tours in the World by TripAd... More

Experience the magic of Chicago at dusk on a 90-minute live guided panoramic adventure that captures the city in its most captivating light. Watch the entire skyline come to life, from Magnificent Mile to Museum Campus and beyond.... More

One of the best ways to explore a city is with a private tour. This tour isn't any different. Have your driver and separate tour guide take you around the most important sites and locations of Chicago. Being a private tour, stop... More

Get an exclusive behind-the-scenes look at the hit NBC drama Chicago Fire TV Show Set Tour. Visit the actual filming locations where the show comes to life. Tour Highlights: - Explore the iconic Firehouse 51 exterior - Visit the... More

Explore Chicago's rich history and vibrant culture on a walking tour starting at Millennium Park with the iconic Cloud Gate sculpture. Wander through lush gardens and public art, then delve into the Chicago Pedway's hidden gems. E... More