As for Chicago, I will add for venues…
Elastic Arts, Comfort Station, The Whistler.
For coffee, my favorites are Passion House, Intelligentsia, Damn Fine in Logan and Wormhole in Wicker Park.
FWIW, if you are by New Wave, don’t go to New Wave if you are looking for legit coffee, Passionhouse and Intelligentsia are worlds better and steps away. New Wave reminds me of a college coffee shop, fun for hanging out when you are younger by the coffee isn’t great.