Penn does have some grad student apartments but these have a reputation for being in terrible, terrible condition: all the older students told me not to live there.

More usefully, Penn has an off-campus housing website only open to Penn people which includes a roommate profile/search system: this is how I found my roommate my first year. This website has some apartment listings from landlords, but those are the kinds of things you can also find on zillow, so it’s mostly useful to find openings in existing student groups that already have a place, and people looking to form groups to find a place.

There are also various facebook groups, such as University of Pennsylvania (PENN) Housing, Sublets & Roommates and University City Off Campus Housing (Upenn, Drexel, U Sciences), which can help you connect with other students to find housing groups. I’d recommend everyone look at look at zillow.com and apartments.com listings semi-regularly, and join those facebook groups, starting at least 3 months before your planned move-in, to get a sense of the market, figure out what you’re looking for, and train yourself to recognize a reasonable deal when you see one. Listings from landlords mostly appear about a month before their desired lease start date, though some are up to 2 months before. Earlier than 2 months in advance, landlords will mostly be trying to fill spaces sooner than you want to move in, but existing roommate groups often try to fill existing spots way before then so they can figure out if they want to renew their leases. So if you’re looking to find or form a roommate group, start looking literally as soon as possible. If you (as a group or individual) are looking to interact with landlords, I’d recommend having a strong sense of what you want and being ready to monitor and jump on new listings by 2 months in advance, though it’s not the end of the world if you’re a few weeks later than that.

Many large landlord companies have their own websites and contacts. Their openings may appear more quickly on their own websites than on 3rd-party websites like zillow. Pro-tip: contact large landlord companies directly to describe what you’re looking for (lowballing your budget very slightly), and their agents have every incentive to show you things as soon as they become available.

Penn is in the easternmost part of West Philly (which refers to west of the Schuylkill River). The immediate surroundings of Penn and Drexel are a neighborhood called “University City”: this is one of many neighborhoods within West Philly. Right next to campus are some super expensive fancy buildings which I think are mainly full of rich undergrads and maybe like MBA students. A bit farther from campus is some much cheaper housing, including apartments and group houses. The further west you go, the cheaper it gets. Just east of the river is Center City: sub-neighborhoods near campus include Logan Square a bit to the north, Rittenhouse Square and Fitler Square just across the river from campus, and Graduate Hospital a bit to the south (south of South Street, which has a bridge going right to campus). Grad Hospital is a bit cheaper than the rest of Center City, especially the further south you go: some consider it the boundary between Center City and South Philly, and it’s where apartment buildings (towards the north) start transitioning into group houses (towards the south).

Get a SEPTA keycard and look at the bus, train, and trolley routes near where you plan to live. If you’re physically in the Bi-Co while you’re looking (which I wasn’t because my first housing search was summer 2020), go into the city and walk around various neighborhoods, explore the transit options, etc.

Most grad students do not have or need cars. Car maintenance is expensive, as is parking in the city. Grad students who do have cars mostly live significantly further west in West Philly, because it’s less dense so the parking is cheaper, and because the cheaper rent helps with car expenses.