The usps flat rate box question - is it possible to book the RT to stay overnight in the change plan

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We are going RT to the Caribbean. Regardless of airline, a change of planes will be required. The question - is it possible to book the RT to stay overnight in the change planes city on the out-going trip? To be more clear, it seems impossible to book online, except by booking the first part of the trip for day 1 and the continuing leg to final destination for day 2 as separate flights with a return on day X a few weeks later. This is substantially more expensive than the "normal" RT. Has anyone managed to include an overnite stay for the same price as without one? If so, helpful hints? Thanks in advance. JCBD
Have you tried to RT ticket? usps flat rate box One from home airport to someplace in FL or San Juan and back; the second RT from FL / San Juan to final destination usps flat rate box and back. We do that as it's about one of the only ways for us to get there. We fly Southwest from Home to FL or SJU and then Jet Blue to STT. Our flights get in too late to make connections on Jet blue, so we stay overnight and fly to islands next day.
Depending on the airline, use the "book by schedule" option, rather than booking by fare, to see if you can "force" an overnight by intentionally picking a first segment that lands too late to make the second leg. What city pairs, what airlines, when?
Well, I know you can book a R/T flight from DFW to several Caribbean islands with a stopover in MIA on the way down. I've overnighted there many times. On the way back I've still connected in MIA but make it back to DFW in one day.
The usps flat rate box question - is it possible to book the RT to stay overnight in the change planes usps flat rate box city on the out-going trip? Probably yes but it might require messing around with ITA Matrix a bit: http://matrix.itasoftware.com/ Have you checked the price of a multi-city itinerary?
A r/t ticket usps flat rate box usually usps flat rate box designates a domestic change as 4 hours and under. usps flat rate box Longer stop is called a stopover. usps flat rate box International change is usually under 24 hours. Different airlines have different rules about changes vs. stopovers. It's also different rules for paid vs. award tickets.
Thanks to all for good suggestions and questions. I've tried one of the suggestions and it was more expensive, but not all, so I'll do that. Home is IAD or DCA. Destination is GCM. Several possible airlines, but prefer Delta, changing planes in ATL. Thank you again.
On Kayak.com , the difference between IAD-GCM-IAD and IAD-MIA(OVERNIGHT)-GCM-IAD is $7. This was using Oct 15-22. If you want to layover in ATL instead of MIA, it becomes a lot more expensive ($842) as you have to stop in MIA, then fly to ATL.
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