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

Mon 21 Oct

Other dates

You can choose the date already on the booking website

Starting at $74.99

Make a reservation

Mon 21 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)

John A

Jun 2018

The two tours I took, with Nick along the Lake side and (sorry forgotten his name but I think it was initials - he’s an actor!) for the Signature Dishes tour, were both wonderful. I feel I learned more about the hidden bits of Chicago than I would have done on any other type of tour. Being able to keep the bike overnight enabled me to see the Chicago skyline at night and also get to the Bean before the rest of the crowds were out of bed. I would certainly hire one of Bobby's bikes on any future trip to Chicago.

Lennert S

May 2018

When you are in Chicago you should for sure do this tour. We did the tour with a group and our fearless leader was Marc. Awesome guy and he can tell you everything you want know. Your going way outside of downtown and that's the best part! You are missing out if you don't do this!

Clubess1

May 2018

Come with an appetite for this tour! My husband and I walked a total of 23 miles in two days while in Chicago, and this tour was part of that exhausting fun! Erica, our guide was pleasant, willing to share info and personal anecdotes, and gave us a bit of history of Chicago as we walked. You will feel like you ate your way through the Loop area, and got a small taste of the foods and beers that Chicago is known for. We especially appreciated that we, who do not eat beef or pork, were given a tin of fries covered with hot dog fixings at the Max's Hot Dog stop (we contacted Bobby's Bikes in advance about this. Thank you!), which was the perfect replacement. It was fun eating nicely-presented, dense and decadent brownies, while looking up at the gorgeous Palmer House ceiling, chatting it up with fellow foodies while at Giordano's, and trying not one, but three different beers at the famous Berghoff bar (plus another, good sized sample at the very hushed, Park Grill, situated under and amidst the support beams of the "bean"). We would liked to have heard a bit more history and info about Chicago's amazing architecture on this tour, but that will just have to wait until our next visit!