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Thoughts??
Also, what do you prefer WFH or WFO?

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I can't compare but Chicago is pretty solid. There are sports leagues, bar culture, etc. Easy to make friends if you want to. It's more of a small town vibe compared to NY I'm sure. Things get quiet after 9pm. It's a city of neighborhoods. Choose wisely. Cost of living is great for the amenities available. Winters are prob a little worse than NY. We don't get much snow but it does get pretty cold. Summer in Chicago can't be beat
Why? It’s offering a third option in the discussion. Most people don’t think of the Twin Cities when relocating because of our snow. We have a vibrant gay community. Fantastic pride, and tons of cultural activities. Not to mention cost of living is less then NY and comparable to some parts of Chicago. Take it or leave it 🤷🏻
Chicago still offers a cosmopolitan city vibe without the magnitude of NYC. I'd say that the advantage of NYC is that gay culture is baked in everywhere across the city, with narrowed pockets like Chelsea. Chicago has Lakeview/Boystown, but that's kind of it. Not that you can't be openly gay across town, but it is very concentrated. I also found Lakeview (having lived there for 8 years) to really attract mid-20s gays (like I was) who want to go out and party. Just my experience! If I moved back to Chicago I'd probably try downtown or West Loop, definitely a more adult vibe.
Don’t forget Andersonville 🙂
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