I had to laugh, that is almost our exact trip we took a few years ago(except we came from Iowa)! We didn't do much sight seeing though...we were just concentrating on getting to Jupiter! My grandparents live down there in the winter! I LOVE IT!!! Do you have kids? One fun place we stopped is in your neck of the woods...not sure where it is from Chicago though. We stopped in Metropolis IL. The kids LOVED it! So much Superman stuff to check out!
Have you been to Jupiter before? We loved Coral Cove there...you could spend an entire day "shelling". Pack a lunch and bring beach shoes! Carlin Park was a little more of a swimming beach then shelling. But both beautiful!!!
We ate at Panama Hattie's on the water...awesome(a little more of a "fun" atmosphere)! Also, at Jetty's...good but a little more pricey and fancier. I think if you get there early, you can eat on the water there too. We just Pricelined all our hotels for the trip there and back.
We also did Lion Country Safari, outside of Jupiter I think.
Have a GREAT time! I am jealous! It has been my fav trip EVER and we even drove with a 2 and 5 yr old!