For vibes: Hyde Park, Pilsen, Uptown, Logan Square, Ukrainian Village, Humboldt Park. These are gorgeous places with wonderful folks, but not the most convenient places to live if you're trying to beebop across the city car-free.

For convenience: West Loop, River North, South Loop, The Loop (no grocery store except Target). These places can be expensive and are full of tech bros and corporate folks. But they're all super convenient for accessing everywhere else in the city.

For amenities: Wicker Park, Lincoln Park, Lakeview, Old Town, Gold Coast, West Town. They've got it all, but can be a bit pricey.

Also check out: Edgewater, Bueno Park, Roscoe Village.

FWIW the Blue Line is suuuuuuuuper shitty these days. I'd steer clear of it your first year here! The rest of the CTA lines and Metra service are fine. My partner and I have lived car-free in Chicago for a year - also moved here from the West Coast. Good luck!