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Chicago Lakefront Neighborhoods Bicycle Tour

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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!
  • 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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All reviews easy ride great tour great sights great afternoon an excellent guide lincoln park zoo great fun hour tour a lot of fun interesting information small group highly recommend this tour peter pace elliot finn safety
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1 - 5 of 62 reviews
Reviewed 4 days ago

Took this toor in early August. There was a child who was struggling on the tour. We spent the whole tour in second gear and the guide did little to help the kid who was struggling, even after we spoke to the guide. so we...More

Date of experience: August 2019
Thank jc44777
jsondak, Manager at Bobby's Bike Hike Chicago, responded to this reviewResponded 4 days ago

Oh my, so sorry to hear that this issue occurred on your bike tour with us. We do have a Tike Hike bike tour for younger riders, but every so often a family may bring someone who isn't an experienced rider. We have protocols in...More

Reviewed 1 week ago

Peter is a super guide-- welcoming, engaging, patient -- and a great story-teller. Highly recommended!!!

Date of experience: August 2019
Thank Orgpia
Reviewed 2 weeks ago

3 of us really enjoyed touring through some of the Chicago neighborhoods, some off the beaten track. Our guide John was great. Very informative and had the right mix of biking, and hearing about the history.

Date of experience: August 2019
Thank Scot L
Reviewed 2 weeks ago via mobile

This is a great way to cover a lot of Chicago. We saw the city from a completely different perspective vs. other types of tours. The ride is easy and the guides are engaging and keep everyone as safe as possible. Gabe and Lake did...More

1  Thank tcommerford
Reviewed 2 weeks ago via mobile

Great overview of areas of Chicago! Bike riding was easy & great way to cover larger area. Tour guides were fantastic! Great stops along the route - family really enjoyed our experience.

Date of experience: August 2019
Thank Krissy M
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Questions & Answers
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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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