To secure the best student housing options in Chicago, it's recommended to start your search 2-3 months before your desired move-in date. Starting to search early ensures you have ample time to explore listings and visit potential apartments. Most students begin looking in February-April for fall semester (August/September move-in) and September-October for spring semester (January move-in), as popular Chicago student housing near campuses like UChicago, UIC, DePaul, and Loyola get booked quickly.