Chicago Tours

UPDATE 2024: Don't be fooled by the copycats out there offering shady copies of our award-winning tours for $1 cheaper! There's only one company that's exclusively offered interiors-themed tours in Chicago for more than a decade, and that's INSIDE CHICAGO WALKING TOURS...

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents....

Taste all of Chicago’s classic eats on this 4 1/2 hour 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 which recently ranked Top 20 in the World by TripAdvisor....

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. ...

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 Buckingham Fountain...

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.   ...

Welcome to Chicago River Boat Architecture Tours! We’re proud to present you with an in-depth, expert architectural-based river boat tour that delves into one of the most remarkable American cities today. Tour departures from 465 N. McClurg Ct....

Looking for fun things to do in Chicago? Explore the city with one of our professional guides on a scenic 6-7 mile Chicago Segway tour. Begin your adventure by gliding through the fragrant garden paths of Grant Park, where you'll admire the iconic 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! Upgrade to the bus tour option to experience the same spine-chilling stories by minibus...

2 hours of being a kid again!!! Take a Segway tour with us and discover how beautiful Chicago truly is. Ride through some of Chicago's most popular destinations with an experienced guide. No matter which tour you choose, it will be a memory lasting a lifetime!...

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....

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...

Few neighborhoods in America combine such delicious cuisine with such fascinating history as Chicago’s Chinatown....

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....

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. ...

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...

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...

Discover horrific instruments of torture and execution. Get a fully audio-guided immersed experience. Explore the interactive exhibits at your own pace. Feel the chilling Ghost Hunting Experience using Ghost Hunting app. ...

Taste some of Chicago's most iconic foods while walking through one of the Prohibition Era’s most fashionable and notorious neighborhoods. Sample prime steak, deep dish pizza and the world famous “Chicago hot dog" while treading the streets of Capone’s closest friends and dreaded enemies...

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...