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!
- Lou Malnati’s Pizzeria - Starting Point for 11am & 11:30am Daytime Tours only. 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
- Gino’s East - Starting Point for 5:30pm Evening Tours only. 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
- 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!
- Wrigley Building - Taste Chicago’s iconic deep dish pizza at one of our most beloved pizza restaurants, and see the first major skyscraper north of the Chicago River.
- Billy Goat Tavern (Millennium Park) - A Chicago institution made famous by a popular SNL skill from the Belushi era. Here, you’ll feast on Chicago-style dogs, the totally unique Windy City interpretation of the hotdog. *NOTE: To ensure you enjoy the best experience possible, we collaborate with several top-notch restaurant partners. While we can’t guarantee the exact restaurant for your tour, rest assured that each option is carefully selected to provide you with a delightful and memorable dining experience.
- Bongiorno’s Cucina Italiana & Pizzeria - Sink your teeth into a delicious Italian beef sandwich. *NOTE: To ensure you enjoy the best experience possible, we collaborate with several top-notch restaurant partners. While we can’t guarantee the exact restaurant for your tour, rest assured that each option is carefully selected to provide you with a delightful and memorable dining experience.
- The Chicago Theatre - Chicago’s iconic theatre Marquee on State Street.
- 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.
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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.
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The Loop - The Loop is Chicago’s bustling business district, named for its location within the rectangular convergence of multiple “El” train tracks.
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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.
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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.
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Palmer House Hilton Historic Lobby - Enjoy the original recipe brownie, which was first invented in Chicago for the 1893 World’s Fair.
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Bobby’s Bike Hike - Chicago Bike, Walking & Food Tours - FREE 2 HOUR BIKE or KAYAK RENTAL INFO:
As an additional perk for booking this particular tour, you will get a FREE 2-hour bike or kayak rental (to be used within (+/-) 3 days of your tour booking. Terms below:
To be used within +/- 3 days of your tour booking.
Bike rentals take place at Bobby’s Bike Hike World Headquarters, 540 N. Lake Shore Drive, Chicago, IL60611. Bike shop is open year-round (excluding Thanksgiving & Christmas).
Kayak rentals take place at Ohio Street Beach, Bobby’s Kayak, 550 E. Grand Avenue, Chicago, IL 60611. Kayak shop open mid-May to mid-October, weather dependent.
Offer excludes Saturday Bike/Kayak rentals between Memorial Day (end of May) Weekend to Labor Day (early September). Kayaking only available from June-September)
No discounts for not using this activity or issues due to weather restrictions. -
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.
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- 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
- Food tasting
- Savor a classic Italian beef sandwich
- Join a local, professional English-speaking guide
- 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
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 through 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 by USA Today and Top 20 in the world by Tripadvisor, offers this ultimate food & walking tour to explore the foods Chicago made famous; a slice of deep-dish pizza, a Chicago-style hotdog, Italian beef, & brownies. Bobby’s expert guides will lead you through downtown Chicago’s most iconic landmarks; Millennium Park, State Street, Chicago Theatre, Chicago Riverwalk, Michigan Avenue, & 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 calm, clear Lake Michigan.
- 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..
For a full refund, cancel at least 24 hours before the scheduled departure time.