Distance from Chicago: 332 miles southwest; 5.5-hour drive
Why it made our list: While Evanston and Champaign-Urbana hog the lion's share of the state's non-Chicago attention, Carbondale is quite content to slip under the radar as one of the state's best college towns. Though the Strip near Southern Illinois University was ground zero for the infamous Halloween riots of the '80s/'90s, these days Carbondale is a friendly and relaxing area to grab a drink at places like The Cellar, PK's, and Hangar 9. Then, be sure to enjoy the surrounding nature, thanks to an astounding 14 parks in the vicinity.
Pro tip: The outdoors is great and all, but when you're looking to fill your belly, nearby Murphysboro is a must, for one reason and one reason alone: 17th Street BBQ, the finest BBQ joint in the state.