If you do Chicago, plan some time to visit the Michigan Lakeshore towns OR head up to Door County. Also, about an hour north of Chicago is Lake Geneva, which is a very nice place.
Maybe I take Chicago for granted a bit, but with its location being so far from anywhere “touristy,” it’s hard for me to wrap my head around coming here for a vacation!
I’d definitely make a plan to ensure there was something decent to do every day, and if the weather is good, it can be great! Hell, we even have Oak Street Beach downtown!
There are some great high end restaurants, some great LOCAL FLAVOR restaurants, and one of our family favorites (Grand Lux Cafe) is right downtown. There’s also drinks at the top of the John Hancock overlooking the Lake, tons of music locations, and cultural activities (sports, museums and theaters) out of the wazoo!
Wait...I take it all back...Chicago is a GREAT place to visit for a week or two! After 30 years I’ve just done all of that! My bad! :-)