Taste food from around the world—and immerse yourself in some of the Windy City's most characterful, locally beloved neighborhoods—on this half-day biking and tasting tour of Chicago. With just a small group for company, you'll follow your guide through the city streets, stopping for views of Chicago’s famous architecture and seeing more than you could if traveling on foot. In between, stop for bites like Polish pierogis, locally made chocolates, and Mexican tacos.
- Enjoy enough generous tastings to add up to a hearty lunch
- Head off the tourist trail and see some of the city’s hippest neighborhoods
- This small-group tour is capped at 14 to keep things personal
- VIP beer package available for purchase (own expense)
What To Expect
Lakefront Trail
The Lakefront Trail has been connecting Chicago’s north and south side neighborhoods since 1963. It spans 18 miles of the beautiful Lake Michigan waterfront and has played a large role in connecting Chicago’s vibrant cycling community.
15 minutes • Admission Ticket Free
Fulton River District
Old meatpacking district turned Chicago hotspot
15 minutes • Admission Ticket Free
West Loop
Chicago’s fastest growing neighborhoods
15 minutes • Admission Ticket Free
Wicker Park
Wicker Park is Chicago’s most famous arts district, home to more bookstores, record shops, and coffee houses per capita than any other neighborhood in Chicago.
10 minutes • Admission Ticket Free
Bucktown
Trendy, eclectic Chicago neighborhood known for great food and dive bars.
15 minutes • Admission Ticket Free
Antique Taco Wicker Park
Enjoy a gourmet Taco
15 minutes • Admission Ticket Included
Bonci Pizzeria
Enjoy an amazing slice of gourmet pizza
15 minutes • Admission Ticket Included
Terry’s Toffee
Toffee to the Stars!
15 minutes • Admission Ticket Included
Cocoa + Co. Coffee and Chocolate Cafe
Enjoy samples from an artisanl chocolatier in Chicago’s Old Town neighborhood
15 minutes • Admission Ticket Included
KASIA’S DELI, INC.
Enjoy Pierogi’s from Martha Stewart’s personal favorite, in the heart of Ukranian Village
15 minutes • Admission Ticket Included
Ukranian Village
Enjoy this unique neighborhood, rated one of the best in Chicago
10 minutes • Admission Ticket Free
Old Town
A neighborhood just north of downtown that survived the Great Chicago Fire of 1871
10 minutes • Admission Ticket Free
River North
Enjoy this neighborhood known for it’s distinct nightlife
5 minutes • Admission Ticket Free
Highlight
Confirmation will be received at time of booking
Minimum age is 18 years
Not wheelchair accessible
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
Tour Operator can accommodate vegetarians or those who don’t eat beef or pork and can cater limitedly for gluten-free and vegan diets.
Near public transportation
Travelers should have a moderate physical fitness level
VIP Adult Beverage upgrade (3 samples) available upon arrival for $19.99 per person extra (Ages 21 )
TripAdvisor rated Bobby’s Bike Hike its highest-level Traveler’s Choice Award each year since 2002.
Our groups have exclusive VIP access to locations we visit.
Operates in all weather conditions, please dress appropriately
Minimum numbers apply. There is a possibility of cancellation after confirmation if there are not enough guests to meet requirements. In the event of this occurring, you will be offered an alternative or full refund.
This tour/activity will have a maximum of 14 travelers
Max group – 14
