We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Chicago Lakefront Neighborhoods Bicycle Tour

  • Get an overview of Chicago's North Side neighborhoods and landmarks
  • Take in views of Lake Michigan while biking along the shore
  • Cover more ground in a short time span on a bike vs. by foot
Chicago Lakefront Neighborhoods Bicycle Tour
From US$46.30
Check Availability
  • Overview
  • What to Expect
  • Important Information
  • Reviews
  • Q&A
Select Date and Travellers
1:30pm Lakefront TourMost Popular
Lakefront Neighborhoods Bicycle Tour
From US$46.30
10:30am Lakefront Tour
Lakefront Neighborhoods Bicycle Tour
From US$57.00
Explore the lakefront districts of Chicago's North Side on a bike tour along quiet streets and waterside paths in the Windy City. You cover ground quickly as you pedal with your guide from Lake Shore Drive to the Magnificent Mile, passing by places such as Oprah’s penthouse, the Playboy Mansion, and Victorian homes in Old Town. Choose from departures in the morning or afternoon for an easy fit with your sightseeing schedule.
What to Expect
Meet your guide at the designated place on Lake Shore Drive to get outfitted with your bicycle and helmet, and hear a short safety briefing.

When ready, set out with your guide on your tour of Chicago’s lakefront neighborhoods. Cruise along the Lake Michigan shore to tree-shaded parks and residential neighborhoods on the North Side, including Rush Street and the Magnificent Mile. Pass by elegant homes and mansions in the Gold Coast Historic District, and popular destinations such as North Avenue Beach and Lincoln Park Zoo.

Hear commentary from your guide about the distinct character of different neighborhoods and highlights such as Oprah Winfrey’s penthouse, Old Town, St Michael's Church, and the Playboy Mansion.

Expect to cycle at a leisurely pace for about 9 miles (14.5 kilometers) of mostly flat terrain. This tour is suitable for all ages and fitness levels, but children should be comfortable riding on city streets.
Reviews (80)
1 - 5 of 38 reviews
Reviewed 1 week ago
Safe, fun and informative tour.

Bobbys bike shop is tucked away up a small ally, but it is well sign posted whe n you are in the area. The tour takes around 2.5 to 3 hrs, and it could be a little longer to be honest as there is so...More

Thank voodoo148
Reviewed 4 weeks ago
Safe, fun professional tour

Very fun, super safe professional and informative tour. Peter was great! Don't let rain discourage you - is still fun.

Thank jsgopher
ceathorne, Manager at Bobby's Bike Hike Chicago, responded to this reviewResponded 3 weeks ago

So glad to hear that Peter treated you well! Thanks so much for choosing Bobby's Bike Hike...even in the rain!

Reviewed 17 October 2018
Great option for exploring Chicago

The pace for the neighborhoods tour was easy, definitely for all riders regardless of skill. Daniella, our guide, was quite knowledgeable and able to share many details about the multiple areas and sites we toured.

Thank HMc46
ceathorne, Manager at Bobby's Bike Hike Chicago, responded to this reviewResponded 17 October 2018

That's so great to hear! We appreciate the review and hope to see you again for another tour in the future! Maybe one with food? ;)

Reviewed 16 October 2018
Great tour

Great tour with an easy ride. Great way to see the city is on a bike. Tour for all levels of riding.

Thank apitman
ceathorne, Manager at Bobby's Bike Hike Chicago, responded to this reviewResponded 17 October 2018

So glad to hear you enjoyed exploring Chicago by bike! We hope you come back for more riding in the future!

Reviewed 11 September 2018 via mobile
Great tour!

Just had a great tour with Sammy Jo! Weather was perfect. Very informative and an easy bike ride. It was recommended from a friend, and I would highly recommend as well.

Thank Stephen H
View more reviews
Questions & Answers
Ask a question
Alice K
5 October 2018|
Response from Francisco M | Reviewed this property |
Better to call the bike rental place. We did morning
Sally S
12 July 2018|
Response from Francisco M | Reviewed this property |
Bobby’s Bike Hike meeting at: Lake Shore Dr. & Ohio St. 540 N. Lake Shore Drive Chicago, Illinois 60611 312-245-9300
30 June 2018|
Response from catkate | Reviewed this property |
about 2 hrs