Hey folks, I wanted to chime in about the area rinks. I've lived in Philadelphia for 20 years and have spent some time in these places.
The UPenn rink is the only one that's truly accessible to the downtown area, but lacks a robust figure skating schedule. There's freestyle once a week, and public skating once per day. Both public and freestyle sessions are an hour long, and at weird hours that most folks with dayjobs can't take advantage of. If you can, avoid the weekend public sessions, especially once LTS starts, since the rink is swarming with children. It's not worth the hassle. I only skate there as a last resort.
Some have already mentioned PSCHS. Want to share my perspective: I have held off on joining for a while because of the cost and all that comes with being a member of a private club. But when I sat down and thought about my long-term goals, joining made sense. I ran the numbers, I realized I wouldn't be spending much for what is essentially drop-in freestyle most days of the week, at hours that are conducive to my work schedule, and I wouldn't have to play the weekly game of "where am I skating this week?" While I'm sure it was harder to join in generations past, it was really easy for me to sign up with PSCHS. Since the rink is open to non-members in the spring, summer, and early fall, I had the opportunity to skate there and meet other folks. I did think about joining WSC, but they cut back their adult hours this season, and I've never really felt comfortable there as I have other rinks, so I opted for PSCHS. (Also, they offer patch, which is like, super-important for me.)
Otherwise, I want to mention that Philadelphia has 5 ice rinks run by the city's Parks & Rec department (Cobbs Creek/Sims, Tarken, Simons, Scanlon, Rizzo). They may not be the fanciest, but they are FREE, most offer 2 hours of public skating per week, and are open Oct-May (more or less). They are in underserved neighborhoods, but if you are concerned about rinks like PSCHS being "too bougie" for your tastes, you will be pleased to find yourself amongst an incredibly diverse and welcoming crowd of folks. I *adore* skating at Sims (the closest to my home) but sometimes the lack of ice supervision and the gaggle of children sometimes can overwhelm me and derail my evening. But if you are looking for a place to skate and you want to keep it low-budget, these rinks are your best bet—and the best-kept secret of the city.
Lastly, I want to mention the Skatium in Havertown. They are a hockey-dominated rink, but probably one of the best sheets of ice in the area. More ice time is available for figure skaters in the off-season, and they have one of the best skate sharpeners in the area. If you have a car, it's a 10 minute drive from the 69th Street Station.