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!
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 - This is the starting point for the 11am & 11:30am daytime tours. Here, participants will meet their lively and engaging guide who will provide an introduction to Chicago’s rich history before enjoying a delicious, cheesy, stuffed Chicago pizza pie.
- Gino’s East - This is the starting point for the 5:30pm evening tours….
- Lou Malnati’s Pizzeria - This is the starting point for the 11am & 11:30am daytime tours. Here, participants will meet their lively and engaging guide who will provide an introduction to Chicago’s rich history before enjoying a delicious, cheesy, stuffed Chicago pizza pie.
- Gino’s East - This is the starting point for the 5:30pm evening tours. Here, participants will meet their lively and engaging guide who will provide an introduction to Chicago’s rich history before enjoying a delicious, cheesy, stuffed Chicago pizza pie.
- The Magnificent Mile - Walk along the elegant Michigan Avenue, passing famous local attractions, and continue to the start of Route 66 to Max’s Take Out, a classic Chicago hot dog stand that has stood the test of time. Inside, discover what makes Chicago’s hot dog so special!
- Wrigley Building - View the first major skyscraper north of the Chicago River.
- Chicago Pedway - In colder months, the guide will utilize the Chicago Pedway system, a network of tunnels, ground-level concourses, and bridges that connect sites throughout Chicago’s central business district, to keep participants comfortable. In warmer months, stroll along the scenic promenades of the Loop.
Expect a leisurely 1.5-mile walk during the 2.5-hour tour, suitable for most fitness levels, with ample stops for tastings and photos. All tastings and beverages are included. Please provide advance notice of any dietary restrictions.
-
Jay Pritzker Pavilion - Available on AM tours only. Designed by the renowned architect Frank Gehry, The Pritzker Pavilion is a stunning and unique band shell located in Grant Park. Its lattice tower of speaker systems ensures full volume for all spectators at numerous summer concerts and movie screenings.
-
The Loop - The Loop is Chicago’s vibrant business district, named for its location within the rectangular convergence of multiple “El” train tracks.
-
The Chicago Theatre - Available on AM tours only. Features Chicago’s iconic theatre marquee on State Street.
-
Cloud Gate - Available on AM tours only. Cloud Gate, affectionately known as “The Bean,” is located in Millennium Park and debuted in 2006. Designed by the acclaimed Indian artist Anish Kapoor, this giant stainless steel masterpiece has become one of the most famous symbols of Chicago arts and culture.
-
Millennium Park - Available on AM tours only. A modern town square with a collection of art, architecture, and gardens that provides a stunning backdrop for hundreds of cultural events. Includes a full tour of the park.
-
Palmer House Hilton Historic Lobby - Available on AM tours only. Enjoy the original recipe brownie, first invented in Chicago for the 1893 World’s Fair.
-
Crown Fountain - Available on AM tours only. Designed by Spanish artist Jaume Plensa, the Crown Fountain features two fifty-foot tall statues of glass brick that display the LED faces of over 1000 Chicagoans laughing, smiling, and spitting.
-
Bobby’s Bike Hike - Chicago Bike, Walking & Food Tours - FREE 2 HOUR BIKE or KAYAK RENTAL INFO:
As an added benefit for booking this tour, participants receive a FREE 2-hour bike or kayak rental (to be used within (+/-) 3 days of the tour booking. Terms below:
To be used within +/- 3 days of the tour booking.
Bike rentals are available at Bobby’s Bike Hike World Headquarters, 540 N. Lake Shore Drive, Chicago, IL 60611. The bike shop is open year-round (excluding Thanksgiving & Christmas).
Kayak rentals are available at Ohio Street Beach, Bobby’s Kayak, 550 E. Grand Avenue, Chicago, IL 60611. The kayak shop is open from mid-May to mid-October, weather permitting.
Offer excludes Saturday bike/kayak rentals between Memorial Day (end of May) Weekend to Labor Day (early September). Kayaking is only available from June to September.
No discounts for not using this activity or issues due to weather restrictions. -
Historic Water Tower - Available on PM tours only. Chicago’s Historic Water Tower is located at the north end of the Magnificent Mile and is one of the few buildings to have survived the Great Chicago Fire.
-
Holy Name Cathedral - Available on PM tours only. As one of the largest cathedrals in North America, Holy Name Cathedral is a remarkable achievement in architecture and community building, representative of Chicago.

- 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,…
- 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)
- Alcoholic beverages
- Hotel pickup and drop-off
- $10 per person (or more) recommended gratuity for guide (Cash, Venmo and PayPal)
- Alcoholic beverages
This tour is ideal for newcomers to Chicago or anyone eager to discover the city’s renowned cuisine alongside its top attractions, all in one experience. Wander through the charming streets of downtown Chicago and savor the Windy City’s beloved dishes! Bobby’s Bike Hike, recognized for its food tours as Top 10 in America (USA Today) and Top 20 globally…
This tour is ideal for newcomers to Chicago or anyone eager to discover the city’s renowned cuisine alongside its top attractions, all in one experience. Wander through the charming streets of downtown Chicago and savor the Windy City’s beloved dishes! Bobby’s Bike Hike, recognized for its food tours as Top 10 in America (USA Today) and Top 20 globally (Tripadvisor), presents this ultimate food and walking tour. Experience the iconic, hearty foods that Chicago is famous for: a slice of deep-dish pizza, a Chicago-style hotdog, Italian beef, popcorn, and brownies. Bobby’s knowledgeable guides will take you through downtown Chicago’s most famous landmarks, including Millennium Park, State Street, Chicago Theatre, Riverwalk, Michigan Avenue, and the Wrigley Building, while sharing stories from Chicago’s rich culinary history. Enjoy your food tour and receive an additional 2-hour FREE bike or kayak rental with each ticket purchased, enhancing your adventure. Cycle along the Lakefront Trail or paddle on 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.
For a full refund, cancel at least 24 hours before the scheduled departure time.