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Not reasonable to me, maybe if you lived in northwest Indiana/the region (not Chicago, IMO)
Greetings!! I am also queer and lived in Chicago for nearly 12 years up until about 6 months ago. The city is incredible, but if you're planning to drive in and out of it for 4+ hours of your day multiple days a week? That would be a HARD no for me, unless you particularly enjoy extreme switches between Fast & Furious driving and sitting at a complete standstill.
The train would be less stressful, but would take a VERY long time and probably cost more than you would want to spend... Now, if your company will reimburse you and you don't mind doubling your commute, that could be a thing!
Honestly, considering the cost of rent, gas & parking these days, and depending on how often you think you would go out of your apartment to do city things outside of work & on the weekends, it might make more sense to live in IN and travel into Chicago when you're feeling frisky.
If you still want to look into your options, the queerest neighborhoods are these:
- Andersonville
- Bronzeville
- Hyde Park (queer because it's a college neighborhood, good highway access)
- Northalsted (don't search 'Boystown', this is what you're looking for)
- Pilsen (more artsy than stereotypically gay, but also has good highway access)
- Rogers Park (Very queer & affordable, also VERY far north)
Pro
I wouldn’t do it. You’ll be miserable making that commute 8+ hours a week.