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.
Bottom Link -1Bottom Link -2AdultKids under 12Kids under 4Custom LineStudents / Seniors 65+Student / MilitaryPrivate Group RequestArrayGift CertificatesArrayReserve NowArrayPRICEHybrid/Comfort: $17.50
Mtn Bike: $19.50
Road Bike: $60.00
Prem Road: $80.00
Tandem: $62.50HighlightsDaley Plaza
Chicago attractions
Chicago neighborhoods
Chicago lakefront
Chicago streets
Happy FridayLEVELEasyDURATIONOvernight RentalSCHEDULEPick-up btw 4–5:30pm Friday
Return btw 8:30am-10am SaturdayPRICEStarting at $15.50LENGTHVariableMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/02/map-graphic.jpg
AGECustom LineStudents / Seniors 65+Student / MilitaryBottom Link -1Bottom Link -2Kids under 12Kids under 4AdultPrivate Group RequestArrayGift CertificatesArrayReserve NowArrayPRICEComfort Bike: $25.00
Child Bike: $20.00
Junior Bikes: $25.00
Child Seat: $18.00
Tandems: $75.50
Road Bikes: $62.00
Premium Road:$79.00
High Performance Mountain Bike: $50.50
Early Bird Pick-up Special at 3pm: $12
Bike Insurance: $5
Helmet Only (no bike): $10.00LEVELEasyHighlightsLake Shore Drive
Great people
Amazing Views
Car-Free Ride
Numerous start points
Good time
Great cause
FREE LOCK
FREE HELMET
FREE MAPDURATIONOvernight RentalSCHEDULEPick-up: 6pm-8pm
May 23, 2020
Return 7am-10:30am
May 24, 2020PRICEStarting at $18LENGTHVariableMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/02/map-graphic.jpg
Bottom Link -1Bottom Link -2AdultKids under 12Kids under 4Custom LineStudents / Seniors 65+Student / MilitaryPrivate Group RequestArrayGift CertificatesArrayReserve NowArrayPRICEComfort/Hybrid: $25.00
Premium Mountain Bike: $35.00
Tandem: $75.50HighlightsNaked Fun
Great people
Chicago neighborhoods
Chicago lakefront
Amazing viewsDURATIONOvernight RentalSCHEDULEP/u: 5:00pm-7pm
on June 13, 2020
Return by 11am
on June 14LEVELRefreshingly EasyPRICEStarting at $25LENGTHVariableMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/02/map-graphic.jpg
Bottom Link -1Bottom Link -2AdultKids under 12Kids under 4Custom LineStudents / Seniors 65+Student / MilitaryPrivate Group RequestArrayGift CertificatesArrayReserve NowArraySCHEDULE1-day & 3-day rentals
Jul 30-Aug 2, 2020PRICE1-Day Rental: $32.00
3-Day Rental (Valid Jul 30-Aug 2): $75.00HighlightsAmazing Music
Beautiful people
Chicago Lakefront
Inexpensive Transportation
Fun FestivalPRICEStarting at $32LEVELVariableLENGTHVariableDURATIONVariableMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/02/map-graphic.jpg
Bottom Link -1Bottom Link -2AdultKids under 12Kids under 4Custom LineStudents / Seniors 65+Map GraphicStudent / MilitaryPrivate Group RequestArrayGift CertificatesArrayReserve NowArrayPRICEStandard Male: $130.75
Standard Female: $130.75
Premium Male: $169.75
Premium Female: $169.75
Pedal Swap: $5.75
Early Bird Pick-up: $20HighlightsBike
Swim
Run
Great peopleSCHEDULEPick-up: 8am-7pm on Aug 29, 2020
Return by 7pm on August 30PRICEStarting at $130LENGTHTriathlonDURATIONTwo-day RentalLEVELVariable
AGECustom LineStudents / Seniors 65+Student / MilitaryBottom Link -1Bottom Link -2Kids under 12Kids under 4AdultPrivate Group RequestArrayGift CertificatesArrayLENGTH26.2 miles if you'd likeReserve NowPRICEComfort/Hybrid
$25.00
Premium Mountain Bike
$35.75
Road Bike
$45.75HighlightsHuge Crowds
Amazing people
Diverse neighborhoods
Cafes/pubs
Flat TerrainDURATIONOvernightSCHEDULEP/U 5:30pm-7pm
Oct 10, 2020
Return by 5pm
October 11PRICEStarting at $25LEVELYou set the levelMap Graphichttps://www.bobbysbikehike.com/wp-content/uploads/2017/02/map-graphic.jpg
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…
- Expect hundreds of thousands of attendees at Chicago Jazz Festival as they flock to Millennium Park to watch top-name jazz performers as they take the stage in Jay Pritzker Pavilion.
- Chicago Critical Mass Bike Ride is an underground bike ride event that takes place the last Friday of every month and includes thousands of riders that ride as a pack through various neighborhoods of Chicago, chiming “Happy Friday.”
- Plan to run with 30,000 of your closest friends in the Bank of America Chicago Marathon. Or support your friends and family who are running by renting a bike to ride the Chicago Marathon course route with Bobby’s Bike Hike.
- Bobby’s Fright Hike: Halloween Edition Bike Tour offers the perfect way to experience Halloween in Chicago. Hear about the haunted side of Chicago as well as the spooky stories that haunt Chicago still.
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.