The perfect Food Tour of Chicago for first timers or anyone eager to explore Chicago's famous foods & top attractions—all in one tour. Stroll the beautiful streets of downtown & taste the Windy City’s favorite eats on this ico... More

Get the best of both worlds: explore Chicago’s stunning architecture while uncovering its dark past. Inspired by Devil in the White City, this expert-led walking tour reveals the secrets of the city’s skyline and its shadowy h... More

Chicago's Chinatown: Few neighborhoods in America combine such delicious cuisine with fascinating history. Join Bobby’s Bike Hike & Food Tours, whose food tours have ranked Top 10 in America by USA Today & Top 20 in the world by... More

Immerse yourself in Chicago's rich history and vibrant culinary scene on this captivating walking tour. Discover the city's iconic architecture and Prohibition-era charm while indulging in delectable local cuisine. From deep-dish ... 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

There’s nothing more magical than downtown Chicago during the holiday season. Bobby’s Bike Hike & Food Tours, internationally recognized for food tour quality, presents our Holiday Hike, a 3hr guided Walking & Chicago Food Tou... More

Beat the crowds with an expert art historian guide on this exclusive early morning tour. Immerse yourself among the masterpieces housed within the acclaimed museum and listen as your guide brings each piece to life by sharing the ... More

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 mo... More

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. On this tour, we will explore the famous and mys... More

You will solve a murder as you learn real Chicago history! Play detective as you unravel a murder mystery, and learn about Chicago's true crime legends and Prohibition secrets. This two-in-one experience combines a rich historic... More

Ready to explore Chicago like never before? Whether you have just a couple of hours or a full day, my personalized city tours offer a unique and unforgettable experience, customizable from 2 to 8 hours. From the iconic skyline to ... More

Join this Chicago haunted pub tour which is a combination ghost tour and pub crawl that will take you on a walking tour to explore the fascinating history of Chicago and hear some of its most famous and creepy haunted stories. A... More

Taste your way through Chicago on this private half-day walking food tour! Savor local favorites like Portillo’s hot dogs, Al’s Italian Beef, deep dish pizza, Garrett’s Popcorn, and Do-Rite Donuts while exploring top city la... More

Walk in the footsteps of Al Capone, John Dillinger, and real life ghost stories while hearing tales of Chicago's haunted past. Visit Prohibition Era speakeasy bars, sites of real life mob shootouts, and haunted tragedies that shap... More

Let our expert local guides share their passion with you for The Art Institute of Chicago on this private 2 hour tour. As you traverse the hallowed halls, you’ll discover an extraordinary collection spanning centuries and cultur... More

There’s nothing more magical than Christmas in Chicago, & this 2hr guided Chicago Walking Tour takes you straight into the heart of it. Journey through the Chicago Loop, Millennium Park, & the Magnificent Mile with an internatio... More

Visit the birthplace of a truly American architecture. Wright’s Oak Park Home and Studio served as both residence and workplace for the first 20 years of architect Frank Lloyd Wright's career. See how he tried out innovative des... More

Come on our chilling ghost tour presented by US Ghost Adventures! Book Directly With Windy City Ghosts and save $5/person. Windy City Ghosts walking Ghost Tour provides a look into the darkness that lurks below Chicago’s busy st... More

The Frederick C. Robie House on the University of Chicago campus is considered one of the most important buildings in the history of American architecture. This Prairie style masterpiece is now a UNESCO World Heritage Site on the ... 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