Bike 10 miles as you sample Chicago staples and see top sights
4 hours
Bike, helmet, food samples
Ride an easy-paced family bike tour with food samples as you cruise past major Chicago attractions, including Millennium Park. Learn the stories behind local favorites like pizza, hot dogs, and Italian beef.
Must be able to ride a bike for 10 miles, with breaks. Some dietary restrictions may have surcharges and may not be fully accommodated—confirm details with Greetwell before booking. If you leave the tour early and leave bikes behind, a $29.99 per bike retrieval fee applies.
Cancel at least 72 hours before the tour for a full refund minus a 10% credit card processing fee. No cancellations within 72 hours. $10/person service fee for weekend reservation changes made within 72 hours. Full refund if severe weather forces the operator to cancel.
This tour lists rates for adults (12+), youth (ages 4–11), and infants (ages 0–3). You also must be able to ride a bike for about 10 miles (with breaks).
Dress for current weather conditions and consider layers. Wear comfortable clothing and shoes (closed-toe shoes preferred). The tour runs rain or shine, and ponchos may be provided if rain is announced.
Tell your dietary needs in advance (vegetarian, vegan, gluten-free, or avoiding pork, beef, chicken, or seafood). Some restrictions may have surcharges, and not all restrictions can be guaranteed. Options are limited for gluten-free or vegan diets.
Bobby's Bike Hike, 540 N. Lake Shore Drive, Chicago, IL 60611
The guides here are consistently stellar, and travelers are quick to name them. Joe, Jeff, Jessika, and several others get enthusiastic shout-outs for being knowledgeable, funny, and genuinely caring hosts who make everyone feel comfortable. These aren't just rehearsed tours – guides share insider tips on where to eat later, adjust for weather needs, and greet past guests like old friends when they bump into them around the city. The food and bike tours seem to be the crowd favorites, taking groups through Chicago's iconic dishes at signature spots while weaving in local history and hidden gems. The routes avoid busy streets when possible, bikes are well-maintained and comfortable, and groups stay small enough that everyone feels looked after. Whether you're exploring downtown, Chinatown, or neighborhood breweries, expect a good mix of sightseeing, storytelling, and excellent eating. Several people mention doing the tour early in their visit so they can revisit favorite spots discovered along the way.
We do a food tour in every new city we visit, and Fran was one of the best! We loved learning all the details of the city as much as trying the food. We will recommend to anyone visiting Chicago!
Tracey Schust
March 30, 2026
We do a food tour in every new city we visit, and Fran was one of the best! We loved learning all the details of the city as much as trying the food. We will recommend to anyone visiting Chicago!
Tracey Schust
March 30, 2026