Chicago Cycling Vacation

Explore Cycling in Chicago


Whether for leisure, exercise or simply to avoid horrendous automobile traffic, cycling in Chicago is a popular means of transport. The Chicago Department of Transportation offers free maps of all the city’s bike trails, including a bike path running along Lake Michigan from the South Side to the North Side with fantastic views of sailboats and skyline. Numerous other off-street paths can be found throughout the city, including paved and multi-use trails in surrounding Cook County Forest Preserves. For cyclists seeking a unique experience, the annual Bike the Drive event each spring shuts down traffic on Lake Shore Drive and opens the road exclusively to thousands powering their own two wheels.


Popular places for Cycling in Chicago

Bobby's Bike Hike

Johnny Sprockets

Lakefront Path

Popular hotels in Chicago

Hyatt Regency Chicago

Chicago - The Drake

W Chicago - Lakeshore

The James Chicago Hotel

Intercontinental Chicago

Amalfi Hotel Chicago

The Palmer House Hilton

Hard Rock Hotel Chicago

Hotel Monaco Chicago Kimpton

W Chicago - City Center