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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

Merrill M

5 star rating: Highly Recommended September 2016

Ryan was very enthusiastic and knowledgeable guide.well worth the time and money.

Arlene C

5 star rating: Highly Recommended August 2016

This is a must do trip! Not only do you see different areas of Chicago up close, you learn much about the history of Chicago. Our guide, Mike, was amazing and knew the answer to every question asked as he had a wealth of knowledge about the city.

Lubov T

5 star rating: Highly Recommended August 2016

It and #39;s the best way to explore the city

Emily B

5 star rating: Highly Recommended July 2016

This tour was excellent! Eddie our guide was friendly and told great stories, and kept our group safe as we rode around. The waterfront section of the ride was particularly cool. Would definitely do another tour with these guys if we are ever back in Chicago. Thank you! :)

Siobhan K

5 star rating: Highly Recommended July 2016

This tour was a highlight of our trip to Chicago. Great fun and a lovely way to see parts of the city you might otherwise miss. The bikes were excellent and the tour was very manageable. Our leader, Elliot was outstanding- knowledgable and enthusiastic but also very safety conscious. He even managed to memorise everyone's names - no mean feat in a group of around 30 people. If you are coming to Chicago do this tour as it really is first class.

Stacy W

5 star rating: Highly Recommended July 2016

Great fun for kids and adults - lots of great history and facts.

Missy G

5 star rating: Highly Recommended July 2016

Kegan was an awesome tour guide. He was so friendly, he even managed to make my 14 year old daughter smile and have a good time. Would love to do another one next time we are in Chicago.

Albert G

5 star rating: Highly Recommended June 2016

This tour was amazing!

Rahul D

5 star rating: Highly Recommended June 2016

A must do thing for tourists in Chicago. After visiting all the main sight seeing places in Chicago, you must take up this tour and enjoy cycling around some interesting areas of the city while enjoying amazing views. You get to meet fellow tourists from around the world. The guide is friendly and explains everything nicely.

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.

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