In the course of looking for flights from CT to NOLA, I found this gem:
16hrs 40min - 3 Stops
Start in New Haven, CT (NVH)
Change planes in Philadelphia, PA (PHL)
Change planes in Boston, MA (BOS)
Change planes in Charlotte, NC (CLT)
Land in New Orleans, LA (MSY)
Wait, what? CT to PA to MA to NC to LA>? So, it goes South, then North past point of origin, then South past point of origin AGAIN, then finally figures out where it's going, and heads further South to get to the right place? Yeah, that's ok....
Oh, and the price for this flight? $1061. It leaves mid-afternoon and arrives the next day.