Cycling in Chicago

If you’re thinking about cycling around Chicago, you’re in for a treat. The city has way more bike-friendly routes than most people realize, from lakefront trails to neighborhood streets that feel surprisingly calm once you dodge the downtown rush. The Chicago Lakefront Trail is the obvious go-to, stretching over 18 miles along Lake Michigan with some of the best skyline views you’ll get on two wheels. But park yourself near 31st Street Beach on a sunny weekend and you’ll see locals cruising with families or just soaking up the breeze.

One thing locals swear by is checking out the 606 Trail. It’s quieter than the lakefront and winds through neighborhoods like Logan Square and Wicker Park, where you can pop into a coffee shop or grab a slice of deep-dish pizza when you stop for a breather. Also, keep in mind that Chicago winters get harsh, but spring and fall are fantastic for cycling,just layer up and be ready for the wind, which can sneak up on you.

Oh, and if you’re not bringing your own bike, Divvy bike-share stations are everywhere downtown and in many neighborhoods. It’s an easy way to hop on and off without worrying about parking or theft. Just a heads up: helmets aren’t required by law but definitely worth wearing since the city traffic can get hectic in spots. Trust me, dressing like a local cyclist means lots of layers and maybe gloves, even in early spring.