Join Chicago Critical Mass as thousands of bicyclists take over the downtown streets on a leisurely bike ride through Chicago. The rides take place on the last friday of every month and are completely free and designed for all types of riders. Chicago's Critical Mass bike rides start from ...Learn MoreBobby’s Bike HikeLearn MoreBottom Link -1Bottom Link -2AdultKids under 12Kids under 4Custom LineStudents / Seniors 65+Student / MilitaryPrivate Group RequestArrayGift CertificatesArrayReserve NowArrayPRICE
Mtn Bike: $19.50
Road Bike: $60.00
Prem Road: $80.00
Tandem: $62.50HighlightsDaley Plaza
Happy FridayLEVELEasyDURATIONOvernight RentalSCHEDULEPick-up btw 4–5:30pm Friday
Return btw 8:30am-10am SaturdayPRICEStarting at $15.50LENGTHVariableMap Graphichttps://1eu32g2n7xjk2vsbqi2chy76-wpengine.netdna-ssl.com/wp-content/uploads/2017/02/map-graphic.jpg
Discounted Chicago bike rentals for all participants and guests. Bobby's Bike Hike is located just 3 blocks from the start/end point of Fifth Third Bank's Bike the Drive. Join 30,000 riders on the world-famous Lake Shore Drive for Chicago's Fifth Third Bank's Bike the Drive, ...Learn MoreBobby’s Bike HikeLearn MoreBottom Link -1Bottom Link -2AdultKids under 12Kids under 4Custom LineStudents / Seniors 65+Student / MilitaryPrivate Group RequestArrayGift CertificatesArrayReserve NowArrayPRICE
Comfort Bike: $35.00
Child Bike: $20.00
Junior Bikes: $25.00
Child Seat: $18.00
Road Bikes: $62.00
High Performance Mountain Bike: $50.50
Early Bird Pick-up Special at 4pm: $12
Bike Insurance: $5
Helmet Only (no bike): $10.00LEVELEasyHighlightsLake Shore Drive
Numerous start points
FREE MAPDURATIONOvernight RentalSCHEDULEPick-up: 6pm-8pm
May 23, 2020
May 24, 2020PRICEStarting at $18LENGTHVariableMap Graphichttps://1eu32g2n7xjk2vsbqi2chy76-wpengine.netdna-ssl.com/wp-content/uploads/2017/02/map-graphic.jpg
(WNBR) is an international clothing-optional bike (or other person powered) event where participants ride en masse for the dual purpose of bringing attention to people powered transport and promoting positive body image. This is not a race, but a massive group ride through the ...Learn MoreBobby’s Bike HikeLearn MoreBottom Link -1Bottom Link -2AdultKids under 12Kids under 4Custom LineStudents / Seniors 65+Student / MilitaryPrivate Group RequestArrayGift CertificatesArrayReserve NowArrayPRICE
Premium Mountain Bike: $35.00
Tandem: $75.50HighlightsNaked Fun
Amazing viewsDURATIONOvernight RentalSCHEDULEP/u: 5:00pm-7pm
on June 13, 2020
Return by 11am
on June 14LEVELRefreshingly EasyPRICEStarting at $25LENGTHVariableMap Graphichttps://1eu32g2n7xjk2vsbqi2chy76-wpengine.netdna-ssl.com/wp-content/uploads/2017/02/map-graphic.jpg
Not sure how you're getting to Lolapalooza? . Bike Rental Specials for Lollapalooza ticket holders. The venue is located in Grant Park, right along the shores of Lake Michigan and the 20-mile Lakefront Bike Trail, which makes biking the most accessible and easiest way to get to/...Learn MoreBobby’s Bike HikeLearn MoreBottom 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, 2020PRICE
1-Day Rental: $32.00
3-Day Rental (Valid Jul 30-Aug 2): $75.00HighlightsAmazing Music
Fun FestivalPRICEStarting at $32LEVELVariableLENGTHVariableDURATIONVariableMap Graphichttps://1eu32g2n7xjk2vsbqi2chy76-wpengine.netdna-ssl.com/wp-content/uploads/2017/02/map-graphic.jpg
Road Bike Rental Specials for all Participants. Includes two-day rental with FREE lock, helmet, and customized service. Pick up Friday afternoon after 2pm for the early bird pick-up fee. Standard Road Bikes are: 2020 Fuji Sportif 2.1 Premium Road Bikes are: 2020 Fuji...Learn MoreBobby’s Bike HikeLearn MoreBottom Link -1Bottom Link -2AdultKids under 12Kids under 4Custom LineStudents / Seniors 65+Map GraphicStudent / MilitaryPrivate Group RequestArrayGift CertificatesArrayReserve NowArrayPRICE
Standard Male: $130.75
Standard Female: $130.75
Premium Male: $169.75
Premium Female: $169.75
Pedal Swap: $5.75
Early Bird Pick-up: $20HighlightsBike
Great peopleSCHEDULEPick-up: 8am-7pm on Aug 29, 2020
Return by 7pm on August 30PRICEStarting at $130LENGTHTriathlonDURATIONTwo-day RentalLEVELVariable
Not running the Chicago Marathon? ! Show support for friends and family and Course. Bobby's Bike Hike offers bike rental specials for people who want to support their family and friends by riding the Marathon Course on a bike. Keep up with you...Learn MoreBobby’s Bike HikeLearn MoreBottom Link -1Bottom Link -2AdultKids under 12Kids under 4Custom LineStudents / Seniors 65+Student / MilitaryPrivate Group RequestArrayGift CertificatesArrayReserve NowArrayLENGTH26.2 miles if you'd likePRICE
Premium Mountain Bike
Flat TerrainDURATIONOvernightSCHEDULEP/U 5:30pm-7pm
Oct 10, 2020
Return by 5pm
October 11PRICEStarting at $25LEVELYou set the levelMap Graphichttps://1eu32g2n7xjk2vsbqi2chy76-wpengine.netdna-ssl.com/wp-content/uploads/2017/02/map-graphic.jpg
Types of Chicago Events
Bobby’s Bike Hike is proud to be involved with many various types of events that balance well with our tenets of Travel, Community, Health, & Service. We are excited to offer discounted 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, Chicago Spring Break specials.
But even smaller organizations and fundraisers, even family reunions, can team up with us to create an event that is perfect for groups who do not want to pay as a group, instead wanting each person to sign up separately. We can create a tour or customized package and provide you with a link for your group to sign up for independently.
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 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. And 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 the America. Whether you’re new to biking or a seasoned veteran, you’ll find Fifth Third’s Bike the Drive an event to remember—nearly five hours of car-free riding along 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.
- 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.
- 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 with Bobby’s Bike Hike and riding the course route.
- 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’ Year Round 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.