Bike Events of Chicago

Offering Discounts on Chicagoland’s biggest festivals and events, keeping you in the know

Chicago Events for the Biking Community

Bobby’s Bike Hike is proud to be involved with many various types of Chicago events that balance well with our tenets of Travel, Community, Health, & Service. 

We offer discounted bike rentals for large scale Chicago events such as Bike the Drive, Chicago Triathlon, Chicago LATE Ride, Chicago’s World Naked Bike Ride, Lollapalooza, Chicago Marathon, and Chicago Spring Break specials.

In addition to these Chicago event bike rentals that allow you to partake in the events and explore the city during the festivities, you can also rent bikes year-round for any occasion. Choose from our variety of bike types (comfort, electric, road, tandem, kids, and more) for private company events and fundraisers or a family event. Work directly with our staff to create an online event listing that allows guests to sign up individually, or make it simple and book an entire group. In addition to bike rentals, private tours and customized packages can be organized for your special event. We can then provide you with a link for your group to sign up for independently.

fans at Chicago's Lollapalooza music festival


Not sure how you’re getting to Lolapalooza? Bike-to-palooza. Bike Rental Specials for Lollapalooza ticket holders.
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hundreds of runners lined up at the chicago marathon starting line

Bike the Chicago Marathon

Not running the Chicago Marathon? Bike the Chicago Marathon!
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riders at chicago's world naked bike ride

World Naked Bike Ride

This is not a race, but a massive group ride through the City. Need a bike rental in Chicago for World Naked Bike Ride?
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bike riders in the chicago triathlon

Transamerica Chicago Triathlon

Road Bike Rental Specials for all Transamerica Chicago Triathlon Participants.
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chicago bike the drive memorial weekend event

Fifth Third – Bike the Drive

For the Fifth Third Bank Bike the Drive, Bobby’s Bike Hike offers overnight bike rental special which includes a helmet and more
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hundreds of bike riders holding their bikes above their heads during chicago's critical mass event

Chicago Critical Mass!

Join Chicago Critical Mass as thousands of bicyclists take over the downtown streets on a leisurely bike ride through Chicago.
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Things to Do in Chicago

There are so many things to do in Chicago, it’s hard to keep up. We’ve put down a few of our favorite Chicago events on this page so you can see what plays well with your upcoming trip to Chicago, or just so you can keep up with what’s going on in Chicago.

In the Spring

Plan your spring break in Chicago where there is an abundance of excitement brewing…

  • Dye the Chicago River Green on St. Patrick’s Day in Chicago and have an incredible Southside Irish parade. Enjoy one of the largest Irish celebrations this side of Dublin.
  • Memorial Day weekend ushers in the Fifth Third Bank’s Bike the Drive, which is a classic Chicago experience and one of the greatest bike rides in America. Whether you’re new to biking or a seasoned veteran, you’ll find Fifth Third’s Bike the Drive a Chicago event to remember—nearly five hours of carefree riding along the iconic Lake Shore Drive in Chicago. All proceeds of this event go towards the Active Transportation Alliance, a Chicago organization geared towards advocacy of better biking, walking, and transit.

In the Summer

Chicago summers are quite possibly the best thing ever….

  • The Chicago Blues Festival is the largest free blues festival in the world and remains the largest of Chicago’s Music Festivals.
  • One of Chicago’s largest summer festivals is the Taste of Chicago, the nation’s premier outdoor food festival showcasing the diversity of Chicago’s dining community. The delicious array of food served at Taste of Chicago is complemented by music and exciting activities for the entire family. We recommend enjoying this Chicago foodie event and going on a more in-depth Chicago Food Tour.
  • Chicago is full of diversity everywhere you look, and we’re proud to host the Chicago Pride Parade, one of the largest pride parades in the country. The streets are lined 12 people deep as 750,000 people cheer the contingents on and enjoy the show, culture and experience!
  • Experience four days of music and entertainment at Lollapalooza, one of the World’s largest music festivals which turns Grant Park, Chicago’s front yard, into a musical playground. You can get discounted bike rentals for Lallapalooza online.
  • Like to stay up late? Like real late? Try Chicago’s L.A.T.E. RIDE to benefit friends of the park.  Join thousands of riders as you ride through Chicago’s urban core through the middle of the night, ending with a sunrise breakfast over Lake Michigan.
  • Or join one of Chicago’s largest summer festivals, the Air and Water Show which causes thousands of spectators to flock to the lakefront while their heads gaze up in amazement as planes and fighter jets buzz overhead.

In the Fall

The weather stays perfect, yet the crowds lessen.  Fall is a wonderful time in Chicago…

In the Winter

Chicago winters may not be known for their pleasantry, but we beg to differ.  Here’s why…

  • In November, Chicago kicks off America’s unofficial holiday shopping season with the Harris Bank Magnificent Mile Lights Parade, which includes a visit from Santa Claus himself.
  • Discover all of the amazing samplings that only on Christmas season in Chicago brings.  Explore the Millennium Park Ice Rink, Chicago’s magnificent City Christmas tree, or Christkindlmarket, a seasonal outdoor market to celebrate the German community in Chicago all on Bobby’s Bike Hike Holiday Hike: Season Sampling Walking Tour
  • Join us on New Year’s Eve for Chi-town Rising New Year’s Celebration, the Midwest’s largest NYE celebration bringing thousands to downtown Chicago to ring in the new year.
  • Looking for a tour to do while Winter is in full swing, you can always try the Chicago Favorites’ Walking & Food Tour which lets you sample Chicago staples of Chicago-style pizza, hot dogs, the original brownie invented right here in Chicago, plus locally crafted beers.  A majority of the tour utilizes the underground pedway system that dissects the loop, to keep you warm on inclement weather days.  So you can see more, and stay cozy.
  • Both the Millennium Park Ice Skating Rink and Maggie Daley Ice Rinks are a fun winter activity to enjoy and stay active even during the winter months.

We have your back Chicago

Bobby’s Bike Hike loves being part of the fabric of Chicago and we take the responsibility to give back to our community very seriously. We love to volunteer and give back to the city we love. Whether it be visiting soup kitchens, singing Christmas carols to seniors around the holidays, participating in the Harris Bank Magnificent Mile Lights Parade, or being an Ambassador through Choose Chicago. If you need our help, please let us know. We are proud to have your back, Chicago.

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