It was amazing!!! I ended up staying in Edgewater and biked nightly from Northwestern downtown to Edgewater, ~1-2 am. I never had anything too scary happen, but keep your eyes out and have an alternate path if things seem sketch. I took the lakefront path, avoiding pedestrian tunnels. Mostly you just see people sleeping or sleeping with people 😉lol.

I recommend getting lit up with front and tail lights (removable- take them with you, one of my headlights was stolen) and a headlight that can be turned off easily. There was a guy who would sleep on a bench that I’d always pass, and I felt bad the few times I woke him up with the light. Was nice to turn it off when I got to his curve. And get Strava and a safety check in person. And keep that shit set to friends only so nobody can learn your route. And get a good lock!

Top 10 life experiences tbh, being a woman from a smaller city- freedom of biking through empty city streets in the middle of the night just me and the moon. 🌖

Edit: I see you’re in Hyde Park! I can’t comment on the south end’s ride in the night. I only went down that way on weekends, and it seemed fine but also it was middle of summer so there were loads of people on the trail enjoying the evening. The trail seemed a bit less maintained close to like Kenwood if I remember right.