City Tours in Chicago
Top 10 Best Chicago City Tours
Found 104 City Tours activities in Chicago. Sort by Popularity.Chicago Architecture River Cruise
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
Chicago River 45-Minute Architecture Tour from Magnificent Mile
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
Chicago Architecture Center River Cruise aboard Chicago's First Lady
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
Chicago: Gangsters and Ghosts Walking Tour
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
Chicago Favorites Ultimate Food and Walking Tour
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
Lake Michigan Skyline Cruise in Chicago
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
Chicago Lake and River Architecture Tour
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
Private 45-Minute Chicago Skyline Helicopter Tour
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
Private Tour
Chicago's Chinatown Food and Walking Tour
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
Private Tour
Chicago Gangsters and Ghosts Luxury Minibus Tour
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
Private Tour
Chicago Craft Brewery Barrel Bus Tour
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
Private Tour
Chicago-Style Holiday Hike: Festive Food and Walking Tour
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
Private Tour
2-Hour Guided Segway Tour of Chicago
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
Private Tour
Chicago Pizza Tour
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
Private Tour
Chicago Helicopter 10-Minute Tour for up to Three Passengers
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
Private Tour
Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour
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
Private Tour
Original Chicago Architecture Interiors Tour: Dazzling Interiors
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
Private Tour
Chicago Walking Food Tour With Secret Food Tours
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
Private Tour
Chicago's Delicious Donut Adventure with Underground Donut Tour
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
Private Tour
Chicago Small Group Food Tour
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
Private Tour