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 iconic Chicago Food Tour! Bobby’s Bike Hike & Food Tours, whose food tours rank Top 10 in America(USA Today) & Top 20 worldwide(Tripadvisor), offers this ultimate walking & food experience featuring the hard-working, salt-of-the-earth classics Chicago made famous: a slice of deepdish pizza, a Chicago-style hot dog, Italian beef, popcorn & dessert. Bobby’s expert guides lead you through downtown’s most iconic landmarks—Millennium Park, State St, Chicago Theatre, Riverwalk, Michigan Ave, & Wrigley Building—while sharing tales from Chicago’s rich, food-loving history. It’s one of the tastiest Things to Do in Chicago! Enjoy your tour & get a BONUS 2-hour FREE bike or kayak rental gift card per ticket. Cruise the Lakefront Bike Trail or paddle Lake Michigan for extra fun!

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. This moving feast incorporates a walk through some of the city's world renowned architecture and public art in the famed Chicago Loop District. Experience our famous deep dish pizza, taste the amazing Italian beef sandwich, enjoy gourmet popcorn, and lots of other treats. Plus, there is our mouth-watering secret dish that you can only find out about on the day of the tour!

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. After the World's Columbian Exposition of 1893, Chicago was determined to become a great cultural and commercial metropolis. This tour is a testament to that era's ambitions. See buildings by Daniel Burnham, Louis Sullivan, Holabird and Roche and other noted architects and hear the stories behind the city's architectural gems. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

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. This moving feast incorporates a walk through some of the city's world renowned architecture and public art in the famed Chicago Loop District. Experience our famous deep dish pizza, taste the amazing Italian beef sandwich, enjoy gourmet popcorn, and lots of other treats. Plus, there is our mouth-watering secret dish that you can only find out about on the day of the tour! As a private tour, everything works around you! Our start times are much more easy going, dates can open up. It's a much more intimate and cozy experience. No need to shout over other tourists, you will have every question answered, and leave feeling like a native yourself!

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 hidden gems off the beaten path, I’ll take you on a journey that captures the heart and soul of this incredible city. I’ll also capture professional photos along the way, so you can take home memories of your adventure. With flexible pickup options, including quick tours during layovers at O'Hare, I make it easy to see the best of Chicago, no matter how much time you have. Book your tour today and let me show you the Windy City through the eyes of a local!

This extraordinary tour of the Prairie Ave District is one not to be missed. Get a sense for how Chicago's wealthiest residents lived around the turn of the century and what remains today. This unique Chicago tour begins with an exploration of one of the city's newly-revitalized spaces: The stunning Chicago Athletic Association Hotel. A short ride on the Green Line takes us to the Prairie Ave District, home to many historic sites such as Motor Row, the former Chess Records and the oldest house in the city. As we wander along Prairie Ave, we're treated to historic mansions and a beautiful park. The highlights of the tour, however, are TWO private, docent-led mini tours at the national landmark Second Presbyterian Church (with its many Tiffany windows) and the Glessner House. We'll also take a mid-tour break at a local employee-owned/woman-owned cafe. Then we board the train back to the Loop for our final stop (and a sweet treat) at the elegant Palmer House Hotel.