Chicago Tour: Downtown Landmarks and Food Exploration
1,098 Ratings
Experience the best of Chicago on this downtown tour that combines iconic landmarks with a delicious food exploration. Taste deep-dish pizza, hotdogs, Italian beef, and more!
Duration: 3 hours
Cancellation: 1 day learn more
  • Lou Malnati’s Pizzeria - Here you’ll meet your entertaining and energetic guide who will give you an introduction to Chicago’s epic history before indulging in a bubbling, cheesy, stuffed Chicago pizza pie
What's Included
  • Expert tour guide
  • Food tasting
What's Not Included
  • Hotel pickup and drop-off
  • $10 per person (or more) recommended gratuity for guide (Cash, Venmo and PayPal)
  • Local craft beer samples can be added for a fee (Three 9oz pours)you can purchase this option upon arrival for $19.99/person
Additional Information

Bobby’s Bike Hike provides the ideal tour for newcomers to Chicago, or those wishing to delve into Chicago’s celebrated foods whilst also taking in the city’s must-see sites, all within a single tour. Wander through the stunning streetscape of downtown Chicago and sample the city’s best-loved dishes. Our walking tours, acclaimed nationally by National Geographic, USA Today, and Conde Nast Traveler Magazine, provide the ultimate gastronomic and pedestrian tour to experience the culinary delights Chicago is best known for; these include deep-dish pizza, Chicago-style hotdog, Italian beef, brownies, along with a VIP upgrade option for three locally brewed beer tastings (you can opt for this upgrade on arrival at $19.99/person). Our knowledgeable guides will take you on a journey through downtown Chicago’s most significant landmarks; these include Millennium Park, State Street, Chicago Theatre, Chicago Riverwalk, Michigan Avenue, and the Wrigley Building, sharing engrossing stories from Chicago’s fascinating food-oriented past.

  • If you have dietary restrictions, please add a note in the special requirements section when booking, and email us after booking to confirm they can accommodate.
  • Tour Operator can accommodate vegetarians or those who don’t eat beef or pork but can’t cater for gluten-free (limited options) or vegan (extremely limited options) diets.
  • VIP Adult Beverage upgrade (3 samples) available upon arrival for $19.99 per person extra (Ages 21+)
  • TripAdvisor rated this tour its highest-level Traveler’s Choice Award each year since 2002.
  • Our groups have exclusive VIP access to locations we visit.
  • Operates in all weather conditions, please dress appropriately
  • Chicago’s famous foods are built on grit, hard work, and on the backs of labor. They are not for everyone, so come with an open mind as we visit Chicago hot dog stand, Deep dish pizza joint, Italian Beef sample, and the original brownie..
Lou Malnati's Pizzeria
North Michigan Avenue
The entrance to Lou Malnati's is in the Wrigley Building, on the northside ground level. Your Guide will be wearing a Bobby's Bike Hike shirt with branded paddle.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
(1098 Ratings)
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Apr 14, 2024
Great outing eating some of Chicago’s local favorites! - Our Guide Brooke was amazing. We got a great combination of some great local food as well as getting informed about Chicago and its history. I would highly recommend it for anyone that wants to get acclimated with the city, have some good food and fun at the same time.
Review provided by Tripadvisor
Apr 14, 2024
Do it! - Our host Brook was amazing. We got to see all of the ‘main’ sites of Chicago while eating and drinking everything that we wanted to try. Highly recommend.
Review provided by Viator
Apr 14, 2024
Good tour paradise - This was amazing. Such a great, informative tour. Architecture, art history, gangland stories, and amazing Chicago foods and their history. Do yourself a favor and do this tour. Do yourself a second favor and request Jeff.
Review provided by Tripadvisor
Apr 13, 2024
Great tour - We had a great time! Lillian was super informative and fun. The food we had on the tour was well picked and we highly suggest this tour if you’re visiting Chicago.
Review provided by Viator
Apr 6, 2024
Chicago rocks! - Ria our guide was amazing! My most memorable moments were learning about Chicago’s rich history throughout the tour.
Review provided by Viator
Apr 3, 2024
BOOK THIS TOUR! - Over Spring Break we went to Chicago! This Food tour was amazing! Our tour guide, Brooke, gave us great history about the city and the Chicago foodie scene. We loved this tour. We would highly recommend it. On the tour was 1 adult and 2 kids (ages 16 & 11). All of us had a great time!
Review provided by Tripadvisor
Apr 3, 2024
Chicago - Food Walking Tour - I had an amazing time yesterday with Brooke and the group. Brooke is very personable, sweet, outgoing and knowledgeable. She gave us great recommendations for the rest of our trip (several us came to Chicago to travel). 10/10 recommend and you’ll be full fersure. The money was well worth it, and happy I was able to exercise in between lol.
Review provided by Viator
Apr 1, 2024
Perfect way to spend a few hours - Brooke was a terrific guide on our tour last week! There were people from Canada, Scotland, and all over the US in our group, which made it really fun. The food was great, the extra little tidbits we learned about Chicago were really cool, and it was fun to try out some new restaurants that we would have probably never stopped at on our vacation. This was a great way to spend a few hours! Remember to dress for the weather, that wind gets a bit cold at times.
Review provided by Tripadvisor
Apr 1, 2024
Yum! - My son and I had such a great time with Brooke! She was fun, energetic and knowledgeable. We left with 3 more great ideas of food to try! Thanks so much!
Review provided by Viator
Mar 31, 2024
So enjoyable - Book it! Heath is fabulous !!! We had a fantastic time learning and eating our way thru Chicago! It is definitely worth the cost & family friendly.
Review provided by Viator
Select Date and Tickets
up to 15 guests
1 Adult
May 2024