Bobby’s Bike Hike Chicago

Because of its flat terrain, interconnected neighborhoods & parks, and miles of bike trails, Chicago consistently ranks as the top city for bicycling in the United States. This means that biking tours are the perfect way to join in on a fun learning experience while getting some exercise!

Started by Jeremy Lewno, who was enchanted by bicycle explorations in Europe, Bobby’s Bike Hike was opened in 2002 with the vision of inspiring Chicago visitors through environmentally sound and culturally beneficial bicycle tours. Named after Jeremy’s father, Bob, the bicycle tourism company began by showing off the beautiful communities of Chicago and has now expanded with food stops and walking tours.

Guests of Bobby’s Bike Hike tours include the use of a bicycle and helmet. In addition to traditional bicycles, electric bikes, child tag-a long bikes and bike trailers are available. Online rates are discounted and the best bikes tend to rent quickly so guest should reserve ahead of time.

Types of Bobby’s Bike Hike Tours

Walking tours, food tours, and (of course) bike tours are all part of the agenda for Bobby’s Bike Hike. Special interest tours may change from season to season, but often include topics such as Chicago’s gangster history, kid-friendly Chicago, foods that made Chicago famous, Chicago nightlife and more.

Bike, food and walking tours are great for visitors, but even native Chicagoans can enjoy a Bobby’s Bike Hike tour. With a pace that is good for almost anyone, each tour is rated at levels so that participants can choose how much physical activity they can manage. Various points of interest provide moments to stop and rest while tour guides tell stories that bring the city to life.

What You’ll See on Bobby’s Bike Hike

Visitors get an insider’s view of Chicago with Bobby’s Bike Hikes. Tours often aim to avoid the most traffic-ridden spots, focusing instead on local communities and areas of interest. While on food tours, guests enjoy locally crafted beers, deep dish pizzas, Chinatown food and culture, lakefront neighborhoods and even an improv comedy tour.

Bobby’s Bike Hike Services

Public and private tours are both offered by Bobby’s Bike Hikes. Call or email to inquire about family groups, scouts, students, corporate retreats, teambuilding outings, etc. Private tours can accommodate from 1-300 people and may be booked in a variety of languages including German, Dutch, French, Spanish, Italian and Portuguese.

Bicycles can also be rented for riding around the city on your own.

At this time, Bobby’s Bike Hike does not provide Segway tours, so for a different type of two-wheeled adventure, guests can head over to Bike and Roll Chicago.

Bobby’s Bike Hike Timing

Tours vary in length, but expect to spend 2-4 hours taking in the sights, sounds and tastes of Chicago’s most interesting neighborhoods.

As expected, more bike tours around Chicago are scheduled for weekends, but at least one usually runs on each week day. Summer is the peak time when more options are available, but the bike tour season runs from March through November. Walking tours are offered year-round and make use of Chicago’s pedway system in the winter months.

Hours of the downtown Chicago headquarters (540 N Lake Short Drive) range from 8am-8pm during peak season to 9am-5pm during the winter. Call ahead to confirm opening days and times.

Bobby’s Bike Hike Considerations

Things you may need to know aboutthe services and accommodations of Bobby’s Bike Hikes:

  • When parking at Bobby’s Bike Hike, the lowest rate in the neighborhood can be found at 441 E Erie Street. Ask at the Bobby’s office for a discount slip to reduce parking costs.
  • All biking tours make water available. Certain tours may include other beverages such as craft beer or hot tea as indicated.
  • Food tours do have options for vegetarians. Ask ahead about gluten-free options.
  • It is recommended to use the restroom prior to arriving at the tour site, but some restroom stops may be made during the tour as well.
  • Reservations can be cancelled with a 72-hour notice (with a 10% processing fee). After 72 hours tours may possibly be re-booked or exchanged for another tour.
  • Tours need a minimum number of people to go out—two for a bike tour and three for a food tour. Rescheduling or cancellation may be necessary if these minimum numbers are not met.
  • Bike tours will go out in rain or shine, so be sure to dress for the weather. Tours may need to be cancelled in case of lightning. Ponchos are available in case of rain.
  • Discounts may be available for military, students, seniors, travel agents, and children.

Book a Bobby’s Bike Hike

Tickets for Bobby’s Bike Hike should be purchased in advance online. Tours often sell out. Booking with is easy online. Online bookings show weekly availability including tour times as well as revealing tours that are already sold out. Pay for your tour in advance with a credit card and receive an email with all of the information you need about where and when tours meet as well as what to expect.

Leave a Comment