Bobby’s Bike Hike turns city streets into storybooks, guiding curious travelers through Chicago and Miami by bike, on foot, and bite by bite. Local guides weave history, architecture, and pop-culture tales with generous tastings o...
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.
Kevin was our tour guide on one of Bobby’s Bike Hikes. I signed up for the lakefront neighborhoods tour. My husband was working in Chicago and I had the whole day to myself to explore— this bike tour was the perfect afternoon activity! Some movement, some beautiful sites, and a lot of sun! I learned funny facts about certain homes (you’d never guess where the first playboy bunny mansion was), I saw a GORGEOUS church, and explored the most stunning areas of Chicago. I would even do this tour again! Thanks so much Kevin and Bobby’s Bikes for making my day off in the city unforgettable!
Olivia Hanifin
September 25, 2025
Kevin was our tour guide on one of Bobby’s Bike Hikes. I signed up for the lakefront neighborhoods tour. My husband was working in Chicago and I had the whole day to myself to explore— this bike tour was the perfect afternoon activity! Some movement, some beautiful sites, and a lot of sun! I learned funny facts about certain homes (you’d never guess where the first playboy bunny mansion was), I saw a GORGEOUS church, and explored the most stunning areas of Chicago. I would even do this tour again! Thanks so much Kevin and Bobby’s Bikes for making my day off in the city unforgettable!
Olivia Hanifin
September 25, 2025
