Chicago Tour: Downtown Landmarks and Food Exploration
1,127 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
(1127 Ratings)
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Jun 12, 2024
Wonderful food, walking tour - Had a lovely evening on this walking food tour. Our guide, Jeff was amazing. We encountered a little longer wait time at one of the restaurants and he was very accommodating and the tour was quite fun. Food was delicious. We definitely hit the highs.
Review provided by Tripadvisor
Jun 12, 2024
Amazing Intro to Chicago - Jeff was terrific! Great pace and mix of history and food. Great group as well. Chicago style only way to go!
Review provided by Viator
Jun 10, 2024
Enraptured by the Windy City - My boyfriend and I have unanimously agreed that Chicago is justifiably an iconic city and undoubtedly a jewel. This was our first visit and experiencing this food tour was the highlight of our trip. The best part of the experience was having Jeff as our tour guide. He was affable, cultured, knowledgeable, and entertaining. If Jeff is your tour guide, be prepared to have an unforgettable and memorable experience.
Review provided by Viator
Jun 10, 2024
Great guide, great food! - I brought my 11-year old adventurous eater and we both had a great experience with the food and our wonderful guide Jeff, aka the Chicago Gandalf! Our favorite was the italian beef but everything was really delicious. Jeff did a great job of entertaining us along the way and making everyone was having a good time. He really knows a lot about Chicago history and I enjoyed learning how many iconic Chicago landmarks originated at the world’s fair.
Review provided by Tripadvisor
Jun 10, 2024
Short trip essential - We had so much fun and learned a lot about Chicago. We only had an afternoon to spend in the city and I really felt this was a great way to really get a feel for the city. Plus the food was amazing! Our tour guild Jeff "Chicago Gandolf" was very knowledgeable and nice.
Review provided by Viator
Jun 9, 2024
CHI-TOWN FOOD TOUR - The history of all the places we went to and Mickey was so much fun and was very patient and kind. Learning the rich history of the city was a great experience.
Review provided by Viator
Jun 9, 2024
An excellent culinary tour! - This was a great tour and experience! Lizzy, our guide, had a great sense of humor and was very knowledgeable. The tour featured the history and several iconic sights, as well as excellent Chicago culinary treats. We loved this tour!
Review provided by Viator
Jun 8, 2024
Great food and walking tour - Mickey hosted my family and I and we had a great time learning about Chicago, and trying the different local favorites. Would recommend!
Review provided by Tripadvisor
Jun 8, 2024
Do it! - Jeff was amazing! Definitely a highlight of our trip. Visiting for work and wanted to see authentic Chicago!
Review provided by Viator
Jun 8, 2024
Chicago Night Tour - The tour guide was knowledgeable and informative about architecture of Chicago. I was disappointed that The Bean was not accessible that should have been disclosed. If you want to take advantage of bike I would recommend the day tour , with the evening tour there is not enough time. I was slightly disappointed also about the beer not offered at three locations. It’s a benefit to try the local beer while on 3 hour tour!!! The food sampling was adequate with food tour. I recommend bringing a jacket it tends to get cooler at night and wear comfortable footwear. Overall I enjoyed walking the city and was totally appreciative of the detail in design and architecture of buildings, Chicago River history, and some odd facts the tour guide shared. The Palmer hotel was spectacular to visit!!!
Review provided by Viator
Select Date and Tickets
up to 15 guests
1 Adult
June 2024