Chicago Tours

Explore some of the most stunning interior spaces you’ll ever see – spaces you’d surely pass by without a second glance if you weren’t shown them by a seasoned, in-the-know tour guide...

Taste all of Chicago’s classic eats on this 4-hr guided bicycle tour! Join the expert tour guides of Bobby’s Bike Hike, America’s longest-running city bike tour company, on this exciting and informative adventure....

We've always had a passion for donuts, but only recently did we realize just how many others do too. And when looking around, we didn't see anything that truly celebrated donuts in all their glory, hence the Underground Donut Tour was born. This tour is for anyone who truly enjoys donuts. ...

Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome. Each architecture river tour is narrated by a professional guide which leads passengers down the Chicago River to discover the city’s most renowned landmarks....

Looking for fun things to do in Chicago? Look no further - Explore Chicago with one of our professional guides on this scenic 7 or 8 mile Chicago Segway tour. Begin these guided Chicago Segway tours traveling through the fragrant garden paths of Grant Park to view Buckingham Fountain....

Looking for fun things to do in Chicago? Look no further - Explore Chicago with one of our professional guides on this scenic 7 or 8 mile Chicago Segway tour. Begin these guided Chicago Segway tours traveling through the fragrant garden paths of Grant Park to view Buckingham Fountain....

Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city, right from the locations that started it all? This tour visits the locations frequented by some of Chicago's most notorious gangsters along with many of the most haunted locations in Chicago! You can get the best of both worlds with this 2 in 1, history-based guided walking tour of Chicago’s gangsters and ghost stories, right from the famous Chicago Loop Vice District! Tour departs from 71 E Wacker Drive...

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. This means you will have two people working with you the entire time, allowing you to get out of the vehicle with your guide at several stops...

Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. Four photo stops are a part of each tour. The small-group atmosphere with a maximum of 10 people ensures a more personal experience. ...

Enjoy Chicago’s famous sights and fabulous skyline views on this award-winning small-group sightseeing tour of the city. The small-group atmosphere with maximum of 10 people ensures a more personal experience.  ...

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, Conde Nast Traveler, and more! Bobby’s now offers over a dozen specialized tours, but The Lakefront Neighborhoods ride is what started it all...

Join us for a fun night of exploring Chicago's crime history on this 2-2. Escape into the city’s criminal underworld as you investigate stories about Al Capone, The Untouchables, the Chicago Mob and more....

Learn about the great architectural landmarks of Michigan Avenue and State Street. The 40 years between 1890 and 1930 saw the creation of some of Chicago’s the most memorable buildings, many of which are featured on this tour. This tour is a testament to that era's ambitions....

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour exclusive guided museum tour, you’ll be able to skip the line and explore it’s most famous pieces with the help of an engaging guide who will lead the way...

Studio W.I.P. by Native 312 Events offers a unique spin on BYOB paint night! Join us as we host an intimate look into the world of Street Art as we learn about some different styles and techniques with guest artists. At the end of your workshop you will be able to go home with your own piece of art!...

There’s never been a better time to be a beer drinker — and Chicago, with its thriving brewery scene and many destination-worthy beer bars, is the perfect city for suds lovers. Visit three of its craft breweries on this all-inclusive, 3. Morning and evening departure times are both available....

Few neighborhoods in America combine such delicious cuisine with such fascinating history as Chicago’s Chinatown. On this 2. This is a totally unique culinary tour experience, and not to be missed! Add a VIP Drink option for alcoholic and ethnic drink pairings at several stops!...

Want a quick introduction to Chicago’s magnificent architecture? This 90-minute tour takes a comprehensive look at the city’s architectural history by viewing buildings in chronological order, from early skyscrapers to new supertall high rises....

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours....

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! This 4-hour guided food and bicycle tour is the perfect way to learn more about how Chicagoans really live, and taste authentic Chicago dishes along the way...