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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!
  • 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 (110)
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All reviews easy ride great tour great sights great afternoon great fun lincoln park zoo an excellent guide interesting information hour tour a lot of fun small group highly recommend this tour peter pace finn elliot safety
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21 - 25 of 72 reviews
Reviewed 17 July 2019 via mobile

It was a hotter than usual day and we were a little concerned about the heat but most of the ride was in the shade and the wind was consistent and it turned out to be a really nice ride. The ride itself was casual...More

Date of experience: July 2019
Thank PerryJoe
Reviewed 12 July 2019

We had 5 children on this tour and had such a great time. Lots of fun and interesting information and lots of great sights for the kids. Highly recommend.

Date of experience: July 2019
Thank Bethany F
Reviewed 9 July 2019 via mobile

My husband and I had a wonderful time on this ride. It was a small group in the morning hours which made it nice. Our guide Nick was awesome. Saw a lot of little cute neighborhoods on the out skirts of downtown and a lot...More

Date of experience: July 2019
Thank Beverly S
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
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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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