There is plenty of stuff to do every weekend. I know there is a German Fest, and a Mexico-fest. There is a Wine-tasting thing downtown. Sox are hosting the KC Royals.
If you do a google on Chicago Events Calendar, you will get several options...some of those sites concentrate on theatre, some on cultural/arts, and some are just general concerts and sports.
With you being out near the ORD airport, there is a newer HofBrau House. I have not tried it yet but want to check out. My wife wants to go to that new outlet mall near there, too.
The El Train takes you all the way downtown for only a couple bucks, and it goes every 10-15 minutes.
Uber is good once you get downtown. I like to walk it, take in the scenery.