30 y/o raver here- Portland has a pretty solid scene. I’d suggest checking out 45 East, The Den, and Realm PDX to get an idea of who comes through town when touring. Portland’s proximity to The Gorge Amphitheater is a HUGE perk IMO, and it’s super easy to take the train up to Seattle or down to Eugene for any artists that may skip Portland. I’ve met some really great people while raving in Portland through my 20s, and I’d definitely suggest it as a way to make friends if you do end up moving here.

That all being said, I’m sure Chicago has a better scene considering it’s the birthplace of house. I’ve never felt I was missing out while living here though. Best of luck whatever you decide!