re: OT Cheap Airfare of the Week: Nola-Aruba $301, Punta Cana $320, Mexico City $235

Let me look into this. It's likely a married segments issue, meaning the cheapest ticket you have is MSY-ATL-EYW combined instead of separate MSY-ATL and ATL-EYW. They've made it so most tickets require that the connection be less than 4 hours so that's what we're running into if I had to take a guess. I'll see what I can do.

ETA: After playing around with it, I'm seeing exactly what you're seeing. Roundtrip it's about $432, if you add in a layover or multicity it changes to $536. I've tried one-ways but that won't work since the ATL-EYW fare is real expensive. Your best bet if you want to stay in ATL for a night is to book the last possible connection of the day and have it be a very tight connection. If you miss it, they'll rebook you for the next available flight with seats (which would be the next morning)

If you wanted to fly American and get a long layover in Miami that is possible as it looks like their fares aren't for married segments