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Village Cycle in Old Town.
I prefer Wheels and Sprockets in Evanston.
Nearly New Bicycles in Uptown rocks. I got a vintage bike that was brand new (been sitting in a box in a warehouse for decades) for like $300. Unless you go this route you won’t really find a new bike for under $500 that will last you more than a season or two at best, you’d need to creep your budget up to about $700 ish and get an entry level Specialized or Giant or something
Village cycle for sure