I'm always down for a road trip! Although, my status shall depend on securing full time employment. I've driven from Chicago to NY. You really want to give yourself 2 days to do it. Chicago to Cleveland was about 6.5 hours and Cleveland to NY was close to 7.5 hours. Definitely alot of fun and the time goes fast, especially with multiple drivers. However, since it will only be a weekend, the best bet is to fly because the flights are fairly reasonable. Plus, I know an amazing pizza place (picture above). Its a block from the Sears Tower.