So my parents are coming to visit me for graduation in a few weeks. I thought it’d be nice if we could do a family thing for a day, like drive somewhere nice and maybe spend the night at a B&B. I’ve been living in Chicago for almost a year now but haven’t ventured past the city limits. Any ideas/suggestions would be much appreciated!
Head north up to Wisconsin. Depends on what they would like to do.
Resorts/shows in the Dells and a nearby casino in Baraboo. That’s about 2 hours up from the border.
The Milwaukee art museum rivals any other big city art museums in the US, including Chicago, New York, and Washington. I can’t recall it’s name at the moment but it’s right on the lake and it’s outstanding. It’s the only thing about Milwaukee that impressed me, though I haven’t seen Miller Park yet (except from the highway).
There’s gazillions of places to go antiquing if that’s your bag.
Or cheese wheel stores! Or antique cheese stores – ISTG!
A short drive (about 80 miles Southwest of Chicago) is Starved Rock State Park - Google it and check it out…very beautiful, nice lodges to stay at and many things to do. There is also the new Grand Bear Resort (Utica, Illinois) next door that has even more amenities.
How about a museum or two. Stay in Chicago. Go to the pier. Science and Industry, The Natural History Museum, Museum of Modern Art?
I’m a country boy now. But I grew up on the outskirts of chy town. I had the opertunity to visit for a few days 6 years ago. My Wife and I hit the museums. It is, IMHO a great city (as cities go 
).
The Natural History Museum? Is that the Field Museum, or is it a separate Museum?
People seem to like going to Galena quite a bit. If you or your parents are into antiques or anything like that, you’ll probably really like it.
Oh, yeah, we’re going to do stuff in the city as well. But like I said, I haven’t been able to go anywhere outside of it for the past year (well, I went to Peoria one weekend). Also my parents won’t be staying with me so we thought it’d be nice to spend the night somewhere together as a family. Especially since I won’t see them again for a while.
Thanks for the suggestions, guys. Keep 'em coming. 
Ahhh. Good on ya.
Went to Peoria? Turned it up to 11 ehh?
I kid. Really I do. I lived outside of Bloomington/Normal in my near and early teen years. And no more advise really, other than if you are looking for a nice B&B, I would look north. Central Illinois is, well, central Illinois.
Yes the Field Museum.
My Wife ran a marathon in Chicago a few years ago. It was the first time I had been back for 35 years (I was a kid when we left). My Wife and I had a great time visiting the pier, the museums and going up to the bar in the John Hancock for a few drinks.
Is the Pizzeria Ono still there? The first one?
How about Boobies? They made the best Italian beef on this earth.
I second Starved Rock. The lodge is very nice, as are the rooms (we haven’t stayed in a cabin). The trails are anything from easy-peasy to endurance trials. The woods are beautiful, as are the rock formations and the history is interesting. It’s a nice place to spend an overnight. Call early–they book up fast.
I’d just go on up to Madison, Wisconsin. Awesome farmer’s market right on the isthmus, with gorgeous lakes on either side. There’s a B&B right near the arboretum, I think. I know there are a few in town. State Street is a terrific place for meandering, window shopping, good coffee.
Starved Rock is really, really popular, too much for its own good, from what I’ve heard.
You could hop down to Springfield and see the Abraham Lincoln Presidential Museum. It’s pretty cool.
Lake Geneva, WI is a popular touristy destination. I personally prefer the surprisingly picturesque St. Charles, IL - great antiquing, much better than Galena and Lake Geneva - which is straight west on North Avenue. That’s not the route I’d recommend to get there, but if you don’t want to get lost, it doesn’t get much simpler than that.
Do they enjoy quirky, weird stuff, like an Egyptian pyramid, cheese “castle” or a surreal candy factory? I can recommend some destinations straight north on I-94 if that’s more their speed. There’s also a nice, and relatively quiet, resort hotel right on the lake front in or near Zion (might be labeled Beach Park at that point - can’t remember) if you head that direction.