Illinois Wesleyan will do everything it can to keep students on campus, but it doesn't discourage off-campus living. There are a number of apartments across the street from campus and in surrounding neighborhoods. There is a historic district south of campus that has a number of older homes converted into student living. Franklin Park is the best place to live off campus because it is just far enough from campus to avoid the bubble, but close enough that it is still reasonable to walk to campus. Off-campus living is expensive, but it is comparable to the cost of on-campus housing. Students can opt to continue the meal plan even if they live off campus, so grocery shopping isn't necessarily a must when you live in an apartment.
Perhaps the biggest challenge to living off campus is finding roommates. In order to keep monthly rent payments low, most people move out with four or five friends if they choose to live in a house. Apartments are easier to find, but they are also very similar to some of the nicer on-campus living. A lot of students choose to stay on campus for this reason. However, the houses on Franklin Square are very nice. There aren't many other neighborhoods around Wesleyan that offer as many housing choices, but parts of the neighborhood extend into lower-income areas of town and can be sketchy at times. For most, off-campus living is a great experience that is usually attempted junior or senior year.