Chicago Favorites Ultimate Food & Walking Tour

369 Ratings
  • Live Guide
  • Instant Confirmation
  • E-Ticket
  • 3 hr

Stroll through the beautiful streets of downtown Chicago and taste all of the Windy City’s favorite eats! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, whose walking tours have been recognized nationally by National Geographic, USA Today, and Conde Nast Traveler Magazine. This is Bobby’s quintessential culinary walking tour, complete with a slice of deep-dish pizza, a Chicago-style hotdog, Italian beef sandwich, brownies, as well as an upgrade option that includes locally crafted beer. Bobby’s expert guides will lead you through downtown Chicago’s most iconic landmarks, including Millennium Park, State Street and Chicago Theatre, Chicago Riverwalk, Michigan Avenue, and the Wrigley Building, all the while regaling you with tales from Chicago’s rich food-centric history. This tour is sure to make memories that will last a lifetime!

Itinerary Details

This is a typical itinerary for this product

Stop At:

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

Duration: 20 minutes

Stop At: 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.

Duration: 10 minutes

Stop At: 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!

Duration: 30 minutes

Stop At:

Sink your teeth into a delicious Italian beef sandwich

Duration: 15 minutes

Pass By: Chicago Riverwalk

The Chicago River runs right through the heart of the downtown Chicago skyscrapers. The architecture and river scenery is absolutely stunning.

Pass By: 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.

Stop At:

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.

Duration: 15 minutes

Pass By: The Loop

The Loop is Chicago’s bustling business district, named for its location within the rectangular convergence of multiple “El” train tracks.

Stop At: The Chicago Theatre

Chicago's iconic theatre Marquee on State Street.

Duration: 5 minutes

Stop At: 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.

Duration: 15 minutes

Stop At: 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.

Duration: 15 minutes

Stop At: 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.

Duration: 30 minutes

Stop At: 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.

Duration: 15 minutes
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