Chicago Critical Mass!
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 ...
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Bobby’s Bike Hike
SCHEDULE
Pick-up btw 4–5:30pm Friday
Return btw 8:30am-10am Saturday
LEVEL
Easy
DURATION
Overnight Rental
LENGTH
Variable
PRICE
Hybrid/Comfort: $17.50
Mtn Bike: $19.50
Road Bike: $60.00
Prem Road: $80.00
Tandem: $62.50

Adult
Student / Military
Students / Seniors 65+
Kids under 12
Kids under 4
Highlights
Daley Plaza
Chicago attractions
Chicago neighborhoods
Chicago lakefront
Chicago streets
Happy Friday
Custom Line
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Private Group Request
PRICE
Starting at $15.50
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MB Bike the Drive
Discounted Rentals for all participants and guests. Bobby's Bike Hike is located just 3 blocks from the start/end point of MB's Bike the Drive. Join 30,000 riders on the world-famous Lake Shore Drive for Chicago's MB Financial Bank's Bike the Drive, benefiting the Active Tran...
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Bobby’s Bike Hike
SCHEDULE
Pick-up: 6pm-8pm
May 25, 2019
Return by 10:30am
May 26, 2019
LEVEL
Easy
DURATION
Overnight Rental
LENGTH
Variable
PRICE
Comfort 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: $45.50
Early Bird Pick-up Special at 4pm: $12
Bike Insurance: $5
Helmet Only (no bike): $10.00

Adult
Student / Military
Students / Seniors 65+
Kids under 12
Kids under 4
Highlights
Lake Shore Drive
Great people
Amazing Views
Car-Free Ride
Numerous start points
Good time
Great cause
FREE LOCK
FREE HELMET
FREE MAP
Custom Line
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PRICE
Starting at $18
Gift Certificates
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World Naked Bike Ride
(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 ...
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Bobby’s Bike Hike
SCHEDULE
P/u: 5:00pm-7pm
on June 8, 2019
Return by 10am
on June 9
LEVEL
Refreshingly Easy
DURATION
Overnight Rental
LENGTH
Variable
PRICE
Comfort/Hybrid: $25.00
Premium Mountain Bike: $35.00
Tandem: $75.50

Adult
Student / Military
Students / Seniors 65+
Kids under 12
Kids under 4
Highlights
Naked Fun
Great people
Chicago neighborhoods
Chicago lakefront
Amazing views
Custom Line
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Reserve Now
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Private Group Request
PRICE
Starting at $25
Gift Certificates
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Bike-to-palooza
. 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/from the concerts. Free bike valets will be availa...
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Bobby’s Bike Hike
SCHEDULE
1-day & 3-day rentals
Aug 1-4, 2019
LEVEL
Variable
DURATION
Variable
LENGTH
Variable
PRICE
1-Day Rental: $32.00
3-Day Rental (Valid Aug 1-4): $75.00

Adult
Student / Military
Students / Seniors 65+
Kids under 12
Kids under 4
Highlights
Amazing Music
Beautiful people
Chicago Lakefront
Inexpensive Transportation
Fun Festival
Custom Line
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Private Group Request
PRICE
Starting at $32
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Transamerica Chicago Triathlon
Road Bike Rental Specials for all Participants. Includes two-day rental with FREE lock, helmet, and customized service. Standard Road Bikes are: 2019 Fuji Sportif 2.1 Premium Road Bikes are: 2019 Fuji SL 2.5 If you would like us to install your own pedals, or if you wo...
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Bobby’s Bike Hike
SCHEDULE
Pick-up: 8am-7pm on Aug 24, 2019
Return by 7pm on August 25
LEVEL
Variable
DURATION
Two-day Rental
LENGTH
Triathlon
PRICE
Standard Male: $130.75
Standard Female: $130.75
Premium Male: $169.75
Premium Female: $169.75
Pedal Swap: $5.75

Adult
Student / Military
Students / Seniors 65+
Kids under 12
Kids under 4
Highlights
Bike
Swim
Run
Great people
Custom Line
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PRICE
Starting at $130
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Bike 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 bike. Keep up with your favorite runner and experience the unique Chicago neighborhoo...
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Bobby’s Bike Hike
SCHEDULE
P/U 5:30pm-7pm
Oct 12, 2019
Return by 5pm
October 13
LEVEL
You set the level
DURATION
Overnight
LENGTH
26.2 miles if you'd like
PRICE
Comfort/Hybrid
$25.00
Premium Mountain Bike
$35.75
Road Bike
$45.75

Adult
Student / Military
Students / Seniors 65+
Kids under 12
Kids under 4
Highlights
Huge Crowds
Amazing people
Diverse neighborhoods
Cafes/pubs
Flat Terrain
Custom Line
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Reserve Now
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Private Group Request
PRICE
Starting at $25
Gift Certificates
Gift Certificates
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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 MB Financial 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 MB 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.

Chicago Critical Mass!

MB Bike the Drive

World Naked Bike Ride

Bike-to-palooza

Transamerica Chicago Triathlon

Bike the Chicago Marathon