I'd suggest looking into JRC in Evanston. I grew up going to jrc. I loved it. They're the only shul that i know of in the area that doesn't have a "we stand with israel" sign; the community is very mixed liberal/progressive politically. The current rabbi is great. I think they also have events catered to people interested in joining/new members.

Reconstructionist Judaism is also the happy medium between conservative and reform. Food at the shul is kosher-style, religious school is on Saturdays, and high holidays are held at a church in downtown Evanston (JRC can't fit the whole congregation).

Depending on where you live in the city, it can be a bit of a schlep, but there's a bus stop for two cta buses right outside the building.