Legal Question in Landlord & Tenant Law in Illinois

You're taking a few risks. First, you have an existing tenancy, that would not be terminated just because he wants you to sign a new lease - he'd have to terminate the month-to-month. Even if he gave you a 30-day notice on 12/26, it wouldn't be effective until 2/1 assuming you pay rent on the 1st. And even if he waited properly to 2/1 the likelihood of his getting an order of possession before 4/1 is unlikely, and you'd probably get a 30-day stay pushing it out to around 5/1... but you won't get to 7/1 if he presses things. If he screws up the notice, however, and starts his eviction case too soon, it could be strung out beyond 5/1, but again there are a lot of "ifs" and no guaranty. As to a new lease, there's no cap on what he can demand under the law unless you're in a rent controlled or housing choice situation. But 6/3 isn't a bad date for a new lease and you might talk the landlord into a 6 month deal.... As to paying rent in cash, waive the $ at his face but don't hand it over without getting receipts.