Tour code: 3332DAY
Pedal past the lakefront neighborhoods of Chicago's North Side on this 3-hour bike tour of the Windy City. Follow a local guide along quiet streets, city parks and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. Catch a glimpse of the Playboy Mansion, Oprah’s penthouse and the Victorian houses of Old Town. Select from several departure times in the morning or afternoon.


  • 3-hour bicycle tour through Chicago's lakefront neighborhoods
  • Bike along Rush Street and the Magnificent Mile
  • Glimpse the Gold Coast Mansions, including Oprah's House and the Playboy Mansion
  • See the Historic Old Town District, Lincoln Park Zoo, North Avenue Beach and more!

Recent Photos of This Tour

What You Can Expect

Chicago Lakefront Neighborhoods Bicycle Tour

There is a stop at a Playboy Mansion on this tour

Start your 3-hour bike tour of Chicago's lakefront neighborhoods at Lake Shore Drive, where you’re outfitted with a stylish bicycle and a helmet. After a safety briefing from your guide, set out to discover the Windy City on two wheels.

Follow your guide off the beaten path through scenic parks and along Lake Michigan’s popular shores to quiet residential neighborhoods on the North Side of Chicago, including Rush Street and the Magnificent Mile. You’ll cycle past North Avenue Beach and the Lincoln Park Zoo, and marvel at the elegant homes and brick mansions of the Gold Coast Historic District.

Your guide shares insights about each neighborhood and points out highlights such as St Michael's Church, the Playboy Mansion, Oprah Winfrey’s penthouse and the historic district of Old Town, lined with charming Victorian houses. You’ll hear interesting factoids about how Chicagoans live and develop an appreciation for one of America’s greatest cities.

This tour covers approx. 9 miles (14.5 km) of generally flat terrain at a leisurely pace. Appropriate for all ages and fitness levels, but children should be capable and comfortable with riding on city streets.

Customer Reviews

Van B

5 star rating: Highly Recommended May 2016

Very nice tour, I suggest that guests try to take it on Sunday morning as we did as the traffic is much less than a typical morning. Guide Liz is very good.

Clayton D

5 star rating: Highly Recommended November 2015

This tour was amazing!

Josee L

5 star rating: Highly Recommended November 2015

Really fun. First time we visit a city in bicycle and it will not be the last!

Susan L

5 star rating: Highly Recommended November 2015

Great moment in Chicago! Safe, fun, and interesting facts about Chicago! We loved the neighborhoods and our guide Elliott was great!

Emily W

5 star rating: Highly Recommended October 2015

Wonderful and informative guide!

Barbara H

5 star rating: Highly Recommended September 2015

Great way to see Chicago. Our tour guide, Eddie, was wonderful. Highlight of our visit

Cheryl H

5 star rating: Highly Recommended August 2015

I usually never want to take the time to review our vacation experiences. But, the Bike Tour company went out of their way and showered us with kindness when we couldn't locate them. The gal on the phone literally walked us step by step over the phone to find the location. Even though I was quite frustrated at first, we had an incredible experience.

Gerben S

5 star rating: Highly Recommended August 2015

The Lakefront Bicycle Tour was very entertaining. A great way to learn more about the history of the Chicago neighbourhoods. Our guide did very well and held a good balance between cycling and informative stops.

Nancy L

5 star rating: Highly Recommended July 2015

Great tour and our guide, Jeff, was a bright beacon of good energy and positivity!

Kathy J

5 star rating: Highly Recommended June 2015

We had a great time learning about Chicago's neighbourhoods and the stories of its creation. The bike tour guide has very entertaining. We highly recommend this tour!

From USD $ 48.10

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