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Chicago, setup perfect for someone in their twenties and your money goes decently far.
Chicago is amazing and a lot more affordable....winters suck...but it's still worth it
Can also endorse Chicago
I moved from the Bay to NYC five years ago, no regrets
I also endorse Chicago. I love it here so much. It’s much more affordable than NYC so you can actually afford to enjoy it. There’s the lakefront and the beaches. So many unique neighborhoods that you’re bound to find something that fits your style/interest. It’s still big enough that after 4 years there’s so many things that I haven’t gotten to experience yet. I also love that it isn’t so overwhelming big that it’s easy to make connections with people. Ex: I know my local bartenders, baristas, 7 Eleven cashiers, neighbors, etc. by name and they know me.
I would say don’t rule out DC or Philly! I lived in DC for 7 years in my early 20’s and loved it!