Milwaukee is 80 miles north of Chicago. The weather is usually a few degrees cooler than Illinois. There is a lot of activities there all year long. The Milwaukee symphony is very good and has a new concert hall. There are plays, great German restaurants like Maders, and a yearly State Fair.
Janesville WI is located near the Illinois Wisconsin border north of Rockford. There are beautiful Rotary Gardens and the Family Farm. This farm raises low cholesterol beef and has a house/store open 7 days a week.
North Point Harbor is located very close to the Illinois Wisconsin border. It is a full service marina.