Chicago
The food tours: deep dish taken seriously, donut crawls taken seriously and neighborhood tastings that explain why this city argues about food with such confidence. Pace yourself; the slices are structural.
Explore Chicago’s top sights and iconic foods on this 3-hour walking tour, including deep-dish pizza, hot dogs, and scenic landmarks, with expert guides.
Most Popular“Great exposure to the iconic Chicago food items. Fran also did a great job explaining the architectural high points on our tour route.”
Discover Chicago’s best donuts on a 2-hour walking tour through the Loop, sampling top bakeries with knowledgeable guides and inclusive options.
“The Donut Tour was amazing! All the donuts we tried were great, and they only gave us a quarter of a donut at each stop so we didn’t feel stuffed. Our tour guides, Izzie and Nick, were super excited about their jobs and offered a…”
Discover Chicago’s top landmarks, architecture, and local foods in a compact 5-hour tour. Perfect for first-timers seeking an authentic city intro.
“Excellent Tour guide. David was so knowledgeable, patient and helpful. I was on a rolator David knew exactly where the elevators were located. By preparing for the locations, it made everyone comfortable.”
Discover Chicago’s iconic sights and delicious local foods on this 3-hour guided walking tour, sampling classic bites from deep-dish pizza to Italian beef.
“This was AWESOME!! We loved it. lance our tour guide was so knowledgeable and also clearly loved living in Chicago. The food was so well selected got to try all the must haves of Chicago. Highly recommend.”
Discover Chicago's vibrant Chinatown through a 3-hour guided walking tour featuring authentic food tastings, cultural insights, and historic sights.
“Great tour with plenty of stops and Chinatown history throughout. I was stuffed by the end! Great pace as well.”
Discover Chicago’s diverse pizza scene on this guided 3.5-hour tour exploring four neighborhoods, sampling iconic styles from deep dish to coal-fired.
“Fantastic guide! James was funny and knowledgeable and passionate about pizza…all huge green flags. He took us to places we hadn’t tried before. My boyfriend was very happy about this gift. My son lives locally and he was happy to find some new places to…”
Discover Chicago’s gangster past and iconic foods on this 2-hour walking tour with tastings, historic hideouts, and stories of Capone’s era.
“Everything was perfect! Baylor was fantastic! Great knowledge.”
Discover Chicago's iconic flavors and sights on a 3-hour guided food tour, with free bike or kayak rentals, led by friendly, knowledgeable guides.
“Jeff was amazing he made us all feel like family. He memorized all our names. My family loved his passion for Chicago”
Discover Chicago’s architecture, food, and history on a 4.5-hour guided walking tour. Enjoy tastings, iconic landmarks, and insider stories with a small group.
“We loved the tour and we are so glad we did it. The guide Dave had an infectious enthusiasm for Chicago and had obviously thought about how to present it. We went to places we would never have thought of! The library was extraordinary but…”
Experience Chicago’s diverse neighborhoods and cuisines on this 4-hour bike tour, sampling local foods, enjoying scenic views, and exploring vibrant districts.
“Seeing the neighborhoods in Chicago and trying new food. Everything is planned out and it’s an easy ride.”
Discover Chicago’s iconic foods and landmarks on this 2-hour guided tour blending tastings of hot dogs, deep-dish pizza, and more in River North.
“Dave was AMAZING!! He was personable, funny, and easy to talk to. He made my two day trip to Chicago one to remember! He was so knowledgeable and made every step exciting. I definitely recommend booking the food tour! Thanks for remembering all of our…”
Discover Chicago’s best pizza styles on this engaging 2-3 hour walking tour through River North, the Loop, and Magnificent Mile, led by expert guides.
“Great selection on different types of pizza. Our guide James, was very knowledgeable on the origins behind each style of pizza.”
Explore Chicago’s architecture, history, and iconic dishes on a small-group tour, combining insider stories, landmarks, and local flavors for a memorable experience.
“Excellent tour! The tour guide was very knowledgeable of history and architecture of the city. The food choices were great!”
Explore Chicago on a guided bike tour blending top sights with delicious local foods. Perfect for first-timers and families seeking authentic experiences.
“Fun, sunny day with Joe riding all over the Chicago loop! My 13 yo daughter and I truly enjoyed our bike tour last week. We ended up with a private tour since we were the only family that signed up for the morning excursion. We…”
Discover Chicago's Chinatown through a 2.5-hour food walking tour featuring authentic regional dishes, cultural insights, and lively guides for an enriching experience.
“We took a tour with Jeff (Chicago Gandalf) and it was a blast! He was very knowledgeable and fun and charming, we loved hearing all his fun facts and information about Chinatown. It's clear he really cares about the neighborhood and the community, and that…”
The river runs through an architecture lesson, and the lake applauds.