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...

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....

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...

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...

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....

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 adventure...

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....

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 TripAdvisor and Top 10 Food Tours in America by USA Today! This 4-hour guided food and bike tour is the perfect way to learn more about Chicago's neighboroods and taste authentic Chicago dishes along the way...

Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Explore historic crime scenes with great photo opportunities.H. Holmes and 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.) ...