Chicago Favorites Ultimate Food & Walking Tour

Overview

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!

City: Chicago

Wed 23 Oct

Other dates

You can choose the date already on the booking website

Starting at $74.99

Make a reservation

Wed 23 Oct

Starting at $74.99

Make a reservation

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What's Included

Expert tour guide

Food tasting

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
Operates in all weather conditions, please dress appropriately
If you have dietary restrictions, please add a note in the special requirements section when booking, and email to [email protected] after booking to confirm they can accommodate.
Hand sanitiser available to travellers and staff
Social distancing enforced throughout experience
Gear/equipment sanitised between use

What To Expect

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!

Chicago Riverwalk

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

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.

The Loop

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

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.

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.

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.

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.

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.

Show 7 more stops

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Traveler Photos

Reviews (596)

ThatDudeEP

Sep 2019

We had an amazing tour led by Kevin on Labor Day weekend! He was really engaging and gave some great historical gems on how the neighborhoods came to be. Food was delicious, however would prefer only one beer stop and substitute with another food stop. Great way to see the Downtown/Lincoln Park neighborhoods of Chicago. Tip: If The Cubs are playing the Wrigleyville portion of the tour will be really to cool to bike through. Highly recommend!

akudian

Sep 2019

4-stop food tour with guide Justin took us to eat pizza, a hot dog, a half Italian beef sandwich, and a dessert (also a popcorn at one point). In between places Justin walked us through tourist sites (the Bean, etc.), gave historical information on food and Chicago generally, answered all our group's questions and was extremely nice and personable to deal with at all times. Would be pleased to go on another tour with him. The only downside for us was the last stop, which was anti-climactic, ending at an Italian supermarket rather than a bakery or confectionary, which was underwhelming and confusing. The first 3 foods/food stops were Chicago staples, but this store and its wares had no connection to Chicago history and culture. And for the money charged, it was a meagre portion (one bite-sized dessert and one bite-sized wrapped chocolate - think of a Lindor's chocolate ball).

lolaj1313

Sep 2019

We just wrapped up the walking food tour with Justin and wanted to waste no time singing the high praises of both the tour itself and Justin, our guide. The tour was well thought out with the emphasis on food relevant to Chicago and not just food, for food's sake. Each stop also became an education in the story of Chicago. Beware though, we are not talking about little samples of the food, but full portions so don't eat a large breakfast and wear your stretchy pants! While the tour included 5 stops, the walk from one place to the next allowed us all to walk off a few calories and gave Justin an opportunity to tell us interesting stories about various aspects of Chicago, give recommendations, answer questions, take us to the best photo ops and surprise us with extra goodies. We are so glad we booked this tour and suggest you do the same!