Bike the Drive

Bike the Drive opens DuSable Lake Shore Drive to cyclists for one morning each Labor Day, giving riders a rare car-free route beside Lake Michigan with Chicago’s skyline as a constant backdrop. The early start and large field make this one of the few chances in the city to experience one of its busiest roads entirely on two wheels.

Because the event offers optional distance challenges alongside the main route, families with riders of different abilities can choose a distance that suits everyone rather than forcing a single pace on the whole group. A downtown or lakefront hotel makes the early call time considerably easier to manage, particularly for families bringing bikes and younger riders who need extra time to get organized before sunrise.

The ride begins and ends at Butler Field, where a post-ride festival gives families a reason to linger rather than heading straight home once the route closes. From there, Grant Park and the waterfront sit close enough to explore on foot, extending a single morning of car-free cycling into a fuller Labor Day visit along Chicago’s lakefront.