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Chicago Lakefront Neighborhoods Bicycle Tour

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2 travelers
This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognized for excellence by National Geographic, USA Today, The Associated Press, Conde Nast Traveler, and more! Bobby’s now offers over a dozen specialized tours, but The Lakefront Neighborhoods ride is what started it all. Join one of Bobby’s expert guides on this 3-hour romp through Chicago’s beautiful North Side neighborhoods. See the ever-rising skyscrapers of Streeterville, the luxe residential property of the Gold Coast, the cozy artists’ village of Old Town, and the rolling greenery of Lincoln Park. You’ll finish off with a cruise down the Lakefront Trail, one of the most popular waterfront bike paths in the nation. This leisure-paced journey is sure to make memories that’ll last a lifetime! Tour departs from 540 N. Lake Shore Drive, Chicago.
  • 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
  • Go off the beaten path to parts of Chicago that locals enjoy
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.
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Important Information
Departure Point
540 N Lake Shore Dr, Chicago, IL 60611, USA
Return Details
Returns to original departure point
  • Bicycle
  • Helmet
  • Local tour guide
  • Food and drinks
  • Gratuity for guide (15-20% suggested, Venmo and PayPal available)
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Additional Info
  • Confirmation will be received at time of booking
  • This tour is appropriate for all ages and fitness levels. Professional guides blend quality information, group interaction, and most of all, fun, to create an unforgettable Chicago experience. Bikes are provided. Child bikes, seats and tagalongs are available.
  • Storage for larger bags/items available for free
  • Please note: children must be strong, capable riders and be able to bike for 9 miles
  • This tour/activity will have a maximum of 15 travelers
Cancellation Policy
For a full refund, cancel at least 24 hours in advance of the start date of the experience.
Reviews (114)
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All reviews easy ride great tour an excellent guide great sights great afternoon great fun lincoln park zoo interesting information hour tour a lot of fun small group highly recommend this tour peter pace finn elliot safety
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Reviewed 8 July 2019 via mobile

Nick was great and took us to places that we probably wouldnt have seen otherwise. Plus the skyline pictures are spectacular! The lakefront is just gorgeous definitely do this tour for some great sights

Date of experience: July 2019
1  Thank biaclb
Reviewed 8 July 2019 via mobile

John is an excellent guide!! I recommend this to everyone who visits Chicago!! Toured a lot of the city!

Date of experience: July 2019
Thank Seetheworldbucketlis
Reviewed 6 July 2019 via mobile

Efficient friendly upbeat Bikes in excellent condition Nick managed us well Busy 4th of July weekend but no safety issues with Nick’s leadership.

Date of experience: July 2019
Thank Jennifer H
Reviewed 5 July 2019

We took this bike tour with John our guide. He was a brilliant guide, informative and gave us a few inside tips on some places in Chicago. We really enjoyed the neighbourhood tour and would highly recommend as it is an easy way to see...More

Date of experience: July 2019
1  Thank NZJillyC
Reviewed 1 July 2019 via mobile

Nick J. Energetically lead our tour through the fairly new park areas by the waterfront. I loved that we got to stop at many of the photo spots like "the bean" and rode on the path along the river. Nick was attentive to the needs...More

1  Thank 764AmyH
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Questions & Answers
Ask a question
6 July 2019|
AnswerShow all 2 answers
Response from Rocky G | Reviewed this property |
I do not believe so, we rode in rain, made it fun. They did provide rain jackets
13 June 2019|
Response from Maps13917538478 |
No, most of the tour is on bike paths and sidewalks. Anytime you are riding on the street is in a wide group and you don't have to really deal with cars at all.
5 October 2018|
Response from Francisco M | Reviewed this property |
Better to call the bike rental place. We did morning
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