Chicago: Signature Dishes Bike Tour with Pizza & Craft Beer

Summary

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.

What’s the experience like?

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.

Step-by-step itinerary

Day 1 — 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

Top questions

How long is the Chicago signature dishes bike tour?

The tour lasts about 4.5 hours and covers roughly 13 miles at an easy pace.

What food is included on this Chicago bike tour?

You’ll try deep dish pizza, a gourmet brownie, a Chicago-style hot dog, and samples of local craft beer.

Is this bike tour suitable for beginners?

Yes, it’s designed for all fitness levels and goes at a relaxed pace with plenty of stops.

Are vegetarian options available?

Vegetarians can be accommodated if noted during booking; vegan or gluten-free options are very limited.

Does the tour run if it rains?

The tour operates rain or shine unless there’s extreme weather; dress appropriately.

What neighborhoods does the bike tour visit?

You’ll pass through Gold Coast, Lincoln Park, Boystown/Wrigleyville, downtown areas near Millennium Park and Navy Pier depending on route.

Is there an age minimum for this Chicago food bike tour?

The minimum age is 16 years old to join the group ride.

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.