I like Galena, IL and Lake Geneva, WI. My hubby and I are going to Lake Geneva to celebrate our 10th wedding anniversary next month, because we've had so many great memories up there over the years. We've also been to Galena about 3 times in the past few years.
Benefit of Lake Geneva is that if you take the main drag (Highway 50) straight east you will get to I-90 and then about 5 minutes south is Pleasant Prairie which is a great outlet mall. It would make a great excursion for a day if you went to LG. If you like antiquing and quaint little shops you can drive 20-30 minutes down Route 12 to Richmond, IL. We've stayed at the Cove which is right next to Mill Creek - also condos, also reasonable (this past Mem.Weekend we got $109 online), and it's a quick 1/2 block walk from either to the lake or shops. If you want a little more peace stay at the Abbey (they have a special if you book 3 or more nights) - it's on the other end of the lake, more relaxing (has a nice spa) but you need to drive about 15 minutes to get to the shops. I think a waterfront room is worth it there, it adds to the relaxation mindset. We've taken the boat tours on LG and found them to be very informative if you like to know about all the rich folks that have called that lakeshore home! Great food at Popeye's (world's best nachos) and at the place next door with the funny name...something like Scuttlebutt's. If you haven't been to Egg Harbor there is one in LG now, they have excellent breakfast. Also the Gino's East attached to the Best Western on the lake has EVEN BETTER stuffed pizza than the ones in Chicago, it must be the water...
Galena is a little farther, Eagle Ridge is like the Abbey - you will have to drive 15 minutes or so to get into town and park. There is the DeSoto hotel right in the middle of town you could possibly park and never move the car until you leave. There is a GREAT restaurant Fried Green Tomatoes and a Great pizzeria Procento's (sp?) it is on one the side streets a few doors from main street. We have stayed at the Irish Cottage which is 5 minutes from town and has a spa downstairs. Great Irish food & Music in the pub, on the weekends they have Irish dancers. Free breakfast is more than the usual donut & bagel buffet. Feel free to reply if you want more info or have questions on either!