Chicago Bike & Food Tour: Deep-Dish, Hot Dogs & Lakefront

Pedal through Chicago’s neighborhoods, savoring deep dish, hot dogs, and more on the go.

A 4½-hour guided bicycle food tour in Chicago where you ride past Wrigley Field, the Lakefront Trail and downtown attractions while tasting deep-dish pizza, Chicago-style hot dogs, Italian beef and dessert. Choose between a daytime route through North Side neighborhoods or an evening route through downtown and along the illuminated skyline. Bikes, helmets, water bottle and a local guide are included. Craft beer samples can be added for an extra fee.

Step-by-step itinerary

Stops and time spent at each8 stops

1. 13th Arrondissement15m
2. Chicago Lakefront Trail15m
3. Lincoln Park Zoo5m
4. Chicago Riverwalk5m
5. Grant Park10m
6. Millennium Park15m
7. Navy Pier5m
8. Lake Michigan15m

Chicago Food and Bike Tour Experience

• Ride bicycle along Lakefront Trail
• Stop at The Wiener’s Circle for Chicago-style hot dog
• Visit Lincoln Park and Lincoln Park Zoo
• Explore Northalsted neighborhood by bike
• Stop at Billy Goat Tavern for Italian beef
• Arrive at Wrigley Field and Wrigleyville
• Sample deep-dish pizza
• Enjoy pastries at Bittersweet Pastry Shop
• Try Garretts Popcorn

The experience

You start with a bike, a helmet and a water bottle, then ride 13 miles through Chicago's neighborhoods while stopping to eat. The route splits two ways: the day version heads north toward Wrigley Field and Lincoln Park, passing tree-lined streets, the Gold Coast mansions and North Avenue Beach. The night version stays downtown, rolling past Millennium Park, Navy Pier, the Chicago Riverwalk and Buckingham Fountain as the skyline lights up. Either way, you're moving between stops on your own bike instead of sitting on a bus, which means you feel the city's scale and see the blocks that connect one landmark to the next.

The food stops anchor the ride. Deep-dish pizza comes first: the kind with layers of cheese, tomato sauce and buttery crust that Chicago is built on. Then a loaded Chicago-style hot dog from The Wiener's Circle (mustard, neon relish, onions, tomato, sport peppers, pickle spear, no ketchup) or from a downtown stand on the night route. Italian beef follows, thin-sliced and dipped the way locals order it. Garretts Popcorn, the caramel-and-cheese blend that's been around since 1949, comes next. The day route finishes at Bittersweet Pastry Shop in Lincoln Park with a handcrafted European-style dessert. The night route ends with Garretts. A local guide rides with you, sharing the stories behind each dish and the neighborhoods you pass through: why Wrigleyville matters, what the Gold Coast represents, how the Riverwalk transformed from industrial waterfront into a gathering place.

The tour runs rain or shine and operates at a leisurely pace, so it suits all fitness levels. If you have dietary restrictions (vegetarian, no beef, no pork), note them when you book and email the operator to confirm what they can arrange. Gluten-free and vegan options are extremely limited. Craft beer samples (three 9-ounce pours) can be added for $19.99 per person on arrival if you're 21 or older. The minimum age for the tour is 18. A $15 suggested gratuity for the guide can be paid in cash, Venmo or PayPal.

What’s included

• Bikes, helmets and all gear.
• water bottle.
• 4½-hour guided tour with a local English-speaking guide.
• stops for deep-dish pizza, Chicago-style hot dog, Italian beef and dessert.
• access to both the Lakefront Trail and downtown attractions depending on your route choice.
• craft beer samples available as an add-on for $19.99 per person (ages 21+).

Options for this experience

2 options

5:30pm TourGuide in English · Available from 2 Apr 2027Classic Food Dishes Included: When you arrive, a VIP upgrade is offered, covering 3 adult drink pairings along the route. $19.99 per person. Downtown Attractions Route: The evening tour visits the Gold Coast, River North, the Chicago Riverwalk, Millennium Park, Buckingham Fountain, and the lakefront views.

11:30am TourGuide in English · 11:30Classic Food Dishes Included: When you arrive, a VIP upgrade is offered, covering 3 adult drink pairings along the route. $19.99 per person. Northside & Wrigleyville Route: A daytime neighborhood route past the Gold Coast mansions, Lincoln Park, Lakeview, Wrigleyville (Wrigley Field), and the lakefront.

You'll see the exact price of each option when you check availability.See dates and prices

Information

Lasts 4h 30m, runs every day at 11:30, from US$ 89 per person, with a live guide in English and with free cancellation up to 24 h before.

Days and timesEvery dayDeparts at 11:30

GroupUp to 16

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Book up to2h before

AgesAdult (18 and older) · Under 18: can't be booked

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather or if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated 13 days ago

Good to know

Low physical effortInfant seats availablePublic transport nearby

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

Is this one for you?Choose the day route if you want to see Wrigley Field and the North Side neighborhoods in daylight, or the night route if you prefer downtown landmarks and the illuminated skyline. Both routes cover the same iconic food stops, so the choice comes down to which part of the city and which time of day suit your schedule.

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Top questions

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

What's the difference between the day and night routes?

The day route heads north to Wrigley Field, Lincoln Park and the Lakefront Trail under afternoon sun, passing the Gold Coast, Lincoln Park Zoo and North Avenue Beach. The night route stays downtown, riding past Millennium Park, Navy Pier, Buckingham Fountain, the Chicago Riverwalk and the Loop as the skyline glows. Both routes include the same food stops (deep-dish, hot dog, Italian beef and a final treat), but the neighborhoods and views change completely.

How far do we ride, and is it hard?

The tour covers 13 miles over 4½ hours, but the pace is leisurely and it suits all fitness levels. You're stopping frequently to eat and hear stories, so the riding is broken up and the speed is easy.

What food do we actually taste on this tour?

You stop for deep-dish pizza, a loaded Chicago-style hot dog with mustard, relish, onions, tomato, sport peppers and pickle (no ketchup), Italian beef dipped the way locals order it, Garretts Popcorn (caramel and cheese blend), and either a handcrafted pastry from Bittersweet on the day route or more Garretts on the night route. Craft beer samples can be added for $19.99 per person if you're 21 or older.

Are bikes and helmets provided, or do I need to bring my own?

Bikes, helmets and all gear are included. A water bottle is also provided on the tour.

Can you accommodate dietary restrictions?

The operator can work with vegetarians and those who don't eat beef or pork. Note your restrictions when booking and email them after to confirm. Gluten-free and vegan options are extremely limited, so those diets are difficult to accommodate.

What time do the tours depart?

Two departure times are available: 11:30am for the day route and 5:30pm for the night route. Choose one when you book.