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Have you explored Divvy bike share? A yearly membership is $100, they have electric bikes (if going far distances) and all responsibility is gone once you lock it up!
It’s my go to after my last bike was stolen on day 2
Consider used bikes too! A lot of people get hooked & upgrade their perfectly good bike for carbon or electronic shifting & there are some good deals to be had.
Also sales at REI! I got my fat tire bike for shockingly cheap during the pandemic when everyone wanted a bike. Granted I’m short & it’s a “mens” bike…still very helpful people work there & might have suggestions.
https://workingbikes.org/
Personally a fan of single speeds since they are cheap, easy to care for, and there are basically no hills in Chicago.