I live in Chicago and am looking for somewhere within a 4-6 hour drive where I could be near a beach, rent a little cabin or stay in a B&B or small hotel. Really just looking for somewhere in Wisconsin, Michigan, Indiana or Illinois that I could go for 1-2 nights to enjoy late spring/early summer. I'm also interested in Michigan vineyards but know even less about that than I do about beaches.

I've been looking at the Old Mission area in Michigan (just north of Traverse City). Suppose to be some nice vineyards there. Course that maybe more than 6 hours for you.

Been to Door County?

In Wisconsin, you muight consider Lake Geneva, Madison, or Door County.

A 1 hour 40 minute drive from South Holland, IL to beaches AND vineyards between St. Joseph and Saugatuck

Thanks everyone! I have some places to start now.

I love the South Holland/Saugatuck areas in MI, too. I don't' think you can go wrong in any of those little towns along the west coach of Michigan - all the way up to Traverse City.
Door County, WI is nice. We liked the Fish Creek area.

Door county is fantastic! Its probably at the very top of your driving time, but he amount of things to see and do is limitless. Fish Creek, Egg Harbor, and Sister Bay are tons of fun.