Chicago: Signature Dishes Bike Tour with Pizza & Craft Beer

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Free cancellationTravelers' pick

1/50

Duration4h 30m

GroupUp to 16

LanguagesEN

Mobile ticketAccepted

Cycle Chicago’s flavors from lakefront trails to pizza stops with locals

You’ll ride through Chicago’s neighborhoods on a guided bike tour, sampling deep dish pizza, brownies, hot dogs, and craft beer along the way. Expect stories from locals, laughter outside Wrigley Field, city views along Lake Michigan, and those small moments—like biting into real Chicago pizza—that stick with you long after.

4h 30m

Step-by-step itinerary

Chicago bike tour with food and sights

Ride through Gold Coast neighborhood
Bike in Lincoln Park and visit zoo
Pass vibrant neighborhood with rainbow sidewalks
Ride along Lake Michigan shore
Enjoy Chicago Lakefront Trail
Visit Wrigley Field baseball stadium
Sample deep dish pizza
Bike through Downtown Chicago
See Chicago Riverwalk
Visit Millennium Park
View Buckingham Fountain lights
Stop at Navy Pier
Sample Chicago-style hot dog and craft beer

The Experience

We were already wobbling a little on our bikes by the time we hit the Gold Coast — not from the riding (it’s pretty flat), but because our guide, Mike, had just handed out these ridiculous brownies at the first stop. Still warm somehow, chocolatey in that way you only get when someone local swears by their “secret” bakery. The air smelled like rain was coming off Lake Michigan, but the sun held out. I think I laughed more than I expected, especially when Mike tried to explain the Cubs’ curse outside Wrigley Field — he got so animated he nearly dropped his water bottle.

The day trip bike tour around Chicago felt like a moving picnic. We cruised past rainbow sidewalks in Boystown and old trees in Lincoln Park; there was this moment where all you could hear was our tires humming and some distant music drifting from a rooftop bar. Deep dish pizza came next — thick crust, gooey cheese, sauce on top (which I still don’t fully understand). Our group got quiet for a second while we ate. Someone asked if real Chicagoans actually order it or if it’s just for tourists; Mike just grinned and shrugged, which probably means yes and no at once.

I’d never biked this much in a city before — 13 miles sounds like a lot until you’re actually doing it with good company and plenty of food stops. The lakefront trail is wide and breezy; sometimes you catch whiffs of popcorn from Navy Pier or hot dogs grilling somewhere you can’t quite see. We finished with craft beer samples in some place that looked like it hadn’t changed since the ‘80s (in a good way). There was talk about who invented the Chicago-style hot dog — apparently nobody agrees — and then we sort of lingered before heading back. My legs were tired but in that happy way.

What’s included

Your day includes use of a bicycle and helmet, bottled water to keep you going between bites, generous samples of deep dish pizza, gourmet brownie, classic Chicago-style hot dog, local craft beer tastings (for those 21+), plus guidance from an expert local who keeps things lively—and yes, lots of laughs along the way.

Good to know

Easy physical levelInfant seats availablePublic transport nearby

Operated by Bobby's Bike, Hike & Food Tours - Chicago