I'd have to say my best would have been last year's torturous EWR-IAH-HNL-ORD-IAD-SEA-ANC-SEA-IAH-GRU-ORD-LGA for $414. Got a $400 voucher for VDBing off of IAD-DEN (part of IAD-DEN-SEA) and taking the direct IAD-SEA. Four days of flying topped off by nearly missing my first international business trip with my new employer due to a canceled ORD-EWR which an angel in the RCC got an ORD-LGA leg to get me in and make my flight at EWR.