Regal Bicycles is very fond of Chicago. As Toronto’s sister city, Chicago is a waterfront destination with all the benefits that come with being a North American metropolis: art, food, infrastructure, and, of course, great cycling. Much like Toronto, Chicago has recently embraced biking as a pillar of its local culture. New bike lanes are popping up to bolster an already great selection of rural and urban trails. So, whether you ride a fixie, cruiser, or mountain bike, there’s no better time to cycle in the Windy City. Below, Regal has listed Chicago’s Best Bike Routes.
The Lakefront
This is an obvious place to start. The Great Lakes are some of North America’s most important natural resources, and Chicago’s Lake Michigan is a gem in the crown. A terrific route for novices and veterans alike, start at Montrose Beach, continue south past North Avenue Beach, and take in the city’s skyline and Soldier field. The trail is meant for sharing—runners, pedestrians, and picnickers all make up the fabric of the Lakefront scenery—and you’ll be able to divert to any one of Chicago’s terrific neighbourhoods and landmarks (our favourite being the Frank Gehry-laden Millennium Park).
L.A.T.E. Ride
An annual event that takes place over the Summer Solstice Weekend, the L.A.T.E. (Long After Twilight Ends) Ride is for Chicago’s night owls. The tour starts at 1 a.m. at Buckingham Fountain, and weaves through downtown, the South Loop, Chinatown, the North Side, and the lake, and concludes at dawn in beautiful Grant Park. There’s also a pre-ride party where you can kick off your evening with some libations—responsibly, of course! Remember, you have to pay and register in advance, but it’s worth it. Proceeds go to Friends of the Park, a non-profit dedicated to preserving, protecting, and improving the Greater Chicago’s green spaces.
Illinois Prairie Path
The Illinois Prairie Path is a 98 km network of trails that connects Chicago with its Cook, Kane, and DuPage counties. Established in 1963, this route is probably our favourite, as it has the distinction of being the States’ first successful rail-to-trail project with the majority of the IPP running along the once-right-of-way Chicago Aurora and Elgin Railroad. The crushed limestone surface is well suited for cycling, strolling, and even horse-riding. And the path’s rural majesty is a welcome vacation from the hustle of America’s Second City.
Palos Forest Preserves
The final entry on our list is for more experienced mountain cyclists. This hidden gem starts on Wolf Road and 95th Street in Willow Springs, just outside of the city proper. There are over 125 km of trails here, loaded with both smooth paths and rugged hills. Palos is defined by its ponds, lakes, and winding paths. Saganashkee Slough is a particularly good place to take a break, go fishing, or board a canoe. And be warned: rocks, roots, and washouts mark the terrain, but that’s part of the fun, right? Make sure to review the county’s Rules of the Trail before starting your adventure.
