Seasonal jobs that might turn permanent - 22 weeks in

I am looking at seasonal jobs around Chicago that might lead to something longer. There are 10 people counting on me, so I am trying to be careful. The pay is hourly with weekly deposits. Is it worth applying to several at once?

Thanks for writing this out. I went through something close to it 9 months ago, and it settled down once I kept a simple log of every call and form.

Apply to several. Start dates and schedules change quickly and having options helps.