I would choose the longest routing possible on your flights for the remainder of the year i.e. if you are flying to BOS, take a layover in ATL rather than the direct flight or a layover in MSP or DTW. Taking the longest routing has saved me many times. Other option is a mileage run (which I will be doing since I will be a few $ short). LAX or SFO have some super cheap flights in the first half of December that will allow you to easily clear the hurdle if you have a couple hours to fly down and back.