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Chicago Favorites Ultimate Food & Walking Tour

Overview
The perfect tour for first timers to Chicago or those who want to explore Chicago's famous foods along with the city's top attractions, all on one tour. Stroll the beautiful streets of downtown Chicago & taste the Windy City’s favorite eats! Bobby’s Bike Hike, whose food tours are ranked Top 10 in America (USA Today) & Top 20 in the world (Tripadvisor), offers this ultimate food & walking tour to explore the hard-working, salt-of-the earth foods Chicago made famous; a slice of deep-dish pizza, a Chicago-style hotdog, Italian beef, popcorn & brownies. Bobby’s expert guides will lead you through downtown Chicago’s most iconic landmarks; Millennium Park, State St, Chicago Theatre, Riverwalk, Michigan Ave, & the Wrigley Building, all the while explaining the tales from Chicago’s rich food-centric history. Enjoy your food tour & receive a bonus 2-hour FREE bike or kayak rental for each ticket bought, adding value to your experience. Bike along the Lakefront Trail or kayak on Lake Michigan.
City: Chicago
Sun 11 May
i
You can choose the date already on the booking website
Starting at $84.99
Make a reservation
Sun 11 May
Starting at $84.99
Make a reservation
New York City Tours
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What's Included
Delight in the famed deep-dish pizza at a Chicago pizza icon
Tantalize your taste buds with the renowned Chicago-style hot dog
Enjoy a Free 2-hour Bike Rental or Kayak Rental (weather permitting)
Sample the world's original brownie recipe
Indulge in 4-5 enticing food stops featuring iconic dishes
Receive insider tips on must-see attractions, activities, and culinary delights for your stay
Explore the city's incredible architecture, a harmonious blend of old and new
Additional Info
  • Wheelchair accessible
  • Infants and small children can ride in a pram or stroller
  • Public transportation options are available nearby
  • Transportation options are wheelchair accessible
  • All areas and surfaces are wheelchair accessible
  • Suitable for all physical fitness levels
  • 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..
What To Expect
1
The Magnificent Mile
Then, stroll down elegant Michigan Avenue and pass renowned local attractions before walking down the start of Route 66 to Max's Take Out, a quintessential Chicago hot dog stand that has stood the test of time. Inside, taste what makes Chicago's unique hot dog so special!
2
Wrigley Building
See the first major skyscraper north of the Chicago River.
3
The Chicago Theatre
Chicago's iconic theatre Marquee on State Street.
4
Chicago Pedway
During colder months, your guide will make use of the Chicago Pedway system, a network of tunnels, ground-level concourses and bridges that connects sites throughout Chicago’s central business district, to keep you as cozy as possible. During warmer times of the year, walk along the large scenic promenades of the Loop. Expect to walk at a leisurely pace for 1.5 miles during the 2.5-hour tour, suitable for most fitness levels, with plenty of stops for tastings and photos. All tastings and beverages are included. Please give advance notice of any dietary restrictions.
5
Jay Pritzker Pavilion
Designed by world-famous architect, Frank Gehry, The Pritzker Pavilion is a stunning and unique band shell located in Grant Park. The lattice tower of speaker systems ensures full volume for all spectators at countless summer concerts and movie screenings.
6
The Loop
The Loop is Chicago’s bustling business district, named for its location within the rectangular convergence of multiple “El” train tracks.
7
Cloud Gate
Cloud Gate, located within Millennium Park, is known affectionately as “The Bean” and debuted in 2006. Designed by famed Indian artist, Anish Kapoor, this giant, stainless steel masterpiece has become one of the most famous symbols of Chicago arts and culture.
8
Crown Fountain
The Crown Fountain was designed by Spanish artist Jaume Plensa and features two fifty-foot tall statues of glass brick that showcase the LED faces of over 1000 Chicagoans laughing, smiling, and spitting.
9
Palmer House Hilton Historic Lobby
Enjoy the original recipe brownie, which was first invented in Chicago for the 1893 World's Fair.
10
Millennium Park
A modern town square with a collection of art, architecture, and gardens that provides a stunning backdrop for hundreds of cultural events. Full tour of the park.
Show 7 more stops
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Traveler Photos
Reviews (1000)
Heather L
Mar 2025
Fran was a fun guide and was very knowledgeable of the city. It was my husbands first time in Chicago and he loved it! He got experience the food and famous landmarks all in one tour!
Shervon_B
Mar 2025
Very professional 👏 Very knowledgeable and highly recommended! Loved the pace. I would book another tour with Jeff and I recommend 👌 him for others to be able to learn from his expertise!
RebeccaG1095
Mar 2025
Fran was a terrific guide for our walking food tour! We had a wonderful time and learned a lot! I highly recommend this tour - my 10yo daughter and I had fun

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