Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of the river, up the north branch to the East Bank Club, and then south pas... More

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 feat... More

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. On t... More

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 location... More

The perfect tour for first timers to Chicago or those who want to explore Chicago's famous foods along with the city's top attractions, all on one tour. Stroll the beautiful streets of downtown Chicago & taste the Windy City’s f... More

Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions. Cruise along Lake Michigan and enjoy stunning views of Chicago's renowned skyscrapers from a unique vantage p... More

An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years of fascinating social, cultural and political history, and explores more than a century ... 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

Few neighborhoods in America combine such delicious cuisine with such fascinating history as Chicago’s Chinatown. Join Bobby’s Bike Hike, whose food tours in just the past year have ranked as Top 10 in America by USA Today and... More

Discover Chicago's captivating past on our top-rated Gangsters and Ghosts luxury minibus tour, exploring the iconic Loop and River North neighborhoods, once dominated by notorious Italian and Irish gangs during Prohibition. Delv... More

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-in... More

There’s nothing more magical than downtown Chicago during the holiday season. Bobby’s Holiday Hike is a 3hr guided walking and food tour through the Chicago Loop, brought to you by Bobby's Bike Hike, internationally recognize... More

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. We will glide through scenic and historic ... More

Enjoy Chicago’s only bus guided neighborhood pizza tour.  Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the best pizza.  Your local guide will teach you the science behind ingredient se... More

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... More

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, ... 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

Experience the best travel stories for yourself! Join a local expert and uncover hidden gems. Join us for the ultimate foodie adventure in Chicago’s historic River North area alongside a local guide who can show you the best spo... More

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all the city's biggest food hits, many dishes with roots dating back over 150 years... More

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... More