stay in your comfort zone and then push at the edges until those edges expand

First, I hear you. Biking can be super scary. Especially in traffic or in busy areas.

Here's my experience for some context: I was afraid of biking as a kid and adult for most of my life. As a kid, I would see a large object and then, out of fear, would crash into it. There is probably a word for this? Anyways, I just thought biking wasn't for me at all.

Then, I lived in a remote area in Norway for a while, where I needed to bike to get groceries. The bike lanes were completely removed from traffic, and drivers were almost comically considerate, so I learned to bike again. I actually learned to LOVE biking while I was there and did a 60-mile bike packing trip alone in one day from Støren to Trondheim; it felt like a real accomplishment.

Now, I bike in traffic and all over whatever city I'm living in and truly miss the times when I don't have access to a bike. It's such an elegant mode of transport.

Strategy: So, this is what worked for me; maybe it will help you, too?

a) Only biking in areas where I felt completely safe and not freaked out by traffic or other bikers or anything around me was key. I needed to basically do a self-imposed version of exposure therapy. I needed to bike repeatedly in a way that didn't trigger fear. Then incrementally, I upped the stakes until I became comfortable in different environments, various distances, conditions, etc. Maybe for now, you only bike in open expanses, and that's totally ok?

b) Biking every day along a set route that was predictable but also challenging and pleasurable was important. There was a very pretty cemetery 5 miles from the farm I was living on. I could bike there on a designated bike path and knew the route well; I also knew I would get 10 miles round trip, but I could go farther if I felt brave. And there was a clean, free bathroom at the end of that route. It reduced a lot of anxiety to have a set path and a destination that I enjoyed, while also providing challenges (different elevations).

I linked to the Chicago Botanic Garden because I imagine that might be a nice destination from Skokie, but I'm not sure what kind of distance you're up for. Maybe even just biking to the lakefront or to a local park on a calm path and back would be a nice place to start? Basically, what worked for me was to stay in a comfort zone and then push at the edges of that in ways that felt safe until those edges expanded.

Good luck, hope this helps, and happy biking!! You got this :)