WN typically had 3 nonstop flights between MDW & BUF leaving at 9:00, 13:30 & 22:20 arriving ~2h30 minutes (90 min flight+1 hour time change). If you were to leave after work on Friday you can grab a relatively inexpensive hotel near the airport (there are man) and then drive the nice 3 hour drive to Ithaca the next day. I know you said you had a hotel in SYR but you might be able to find something closer to Ithaca.