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“Awesome tour. Great way to hit the touristy spots without it taking up the whole weekend. Greg was 10/10 and wish he could give every tour.”
Discover Chicago’s best donuts on a 2-hour walking tour through the Loop, sampling top bakeries with knowledgeable guides and inclusive options.
“Nick was awesome. Fun with lots of tidbits about the city. Understood that my daughter only wanted to try some of the doughnuts…did not push at all. Several breaks and opportunities to cool off and get drinks as needed. Would totally do again.”
Discover Chicago’s top landmarks, architecture, and local foods in a compact 5-hour tour. Perfect for first-timers seeking an authentic city intro.
“Dave was very knowledgeable & friendly. Freezing outside but still was able to provide a great experience both inside & outside! I would do this tour again.”
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 such a fun experience and a great way to taste all of the must haves from Chicago! Our guide, Eliot, was super fun and knowledgeable and gave us a great tour. 10/10 would recommend.”
Discover Chicago's vibrant Chinatown through a 3-hour guided walking tour featuring authentic food tastings, cultural insights, and historic sights.
“It was a great experience!! Joe, the guide, was very friendly, enthusiastic, and super knowledgeable. Everything ran smoothly and the food was delicious!! They did a great job putting the tour together and I highly recommend this tour if you have a few hours and…”
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.
“Make sure you come on the tour with an empty stomach. James was an amazing tour guide. Always telling jokes & history about the city. If you are a new tracer in the city. James will let you know where to go.”
Discover Chicago’s gangster past and iconic foods on this 2-hour walking tour with tastings, historic hideouts, and stories of Capone’s era.
“Our guide Baylor was great! She was well informed and friendly. The food was great. Our favorite part was going down to see hidden tunnel in Harry Caray restaurant. Thank you”
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.
“I had a awesome time with Kelly and the group. We got to see a bit of Chicago and taste some delicious food on the way. Everything was well organized an dinteresting.”
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.
“The tour is excellent! It is fun, interesting, and the food is YUMMY! And our guide, Rich Berry, made the whole day extra special.”
Experience Chicago’s diverse neighborhoods and cuisines on this 4-hour bike tour, sampling local foods, enjoying scenic views, and exploring vibrant districts.
“This is our second guided bike tour of Chicago and again was fantastic. Wyatt is a great guide- friendly, knowledgeable, and was adept at getting us through the city safely. Anyone who is fairly comforatble on a bike can do this tour! I gave this…”
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.
“It was such a fun experience to hear about Chicago architecture mixed with food! We loved the pizza and donuts especially! Dave does many tours so we look forward to using him again when we head back to Chicago!!!”
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.
“Our guide was Super knowledgeable. Gave us a great tour with entertaining details and interesting history .”
Explore Chicago’s architecture, history, and iconic dishes on a small-group tour, combining insider stories, landmarks, and local flavors for a memorable experience.
“Rich has been and incredible guide, funny and entertaining with so many information and insights. Tour was perfectly planned and food booked in advance so we didn’t have to wait much, 100% a beautiful experience”
Explore Chicago on a guided bike tour blending top sights with delicious local foods. Perfect for first-timers and families seeking authentic experiences.
“Paul was AMAZING! We were so glad that we did this bike trip! Really allowed us to see the city and feel the vibe! The BEST!”
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.
“York was an excellent guide. Had time for everyone to talk about the history of Chinatown, and the restaurants he brought us to were brilliant.”
The river runs through an architecture lesson, and the lake applauds.