7) Short road trip: Milwaukee, Wis., Grand Rapids, Mich., Indianapolis, Ind., and Ann Arbor, Mich. are all less than five hours away from Chicago. Skip town for a day and be a Midwest tourist for a little while. I love Chicago just as much as the next person, but it’s super refreshing to enjoy the zoos, museums and restaurants that our neighboring cities and states have to offer. Best part, if you get out early enough, you can make it back to your own bed at the end of the night.