I've been stalking for a while and have learned a ton from you all, hoping someone can help me with this, or point me to a more appropriate place to ask this question.

Home airport is DTW. I will be in NYC for business May 1-3, flying back to DTW on the afternoon of the 3rd. I had previously already purchased a flight (DL 1405) to MCO the evening of May 3rd, along with redemption of a companion certificate for my wife.

The issue is that one-way direct flights from JFK to DTW are >$500, but is only $190 if I took a flight from JFK to MCO with a layover in DTW, even though the 1st leg of that flight is the same as the more expensive JFK-DTW flight (DL 95). The 2nd leg of that flight is DL 1405, where I already have a seat.

I unfortunately need to check a bag for the trip to NYC. Would it be possible to book the JFK-MCO flight, exit the terminal and check-in with my wife in DTW (allowing the companion certificate to be used), take that flight, and then pick up my bag in MCO (which had been checked through from my NYC flight)? Or will the system not even let me do that because I would essentially have 2 seats on the same flight? Are there any other options that I'm overlooking?

Thank you very much for your help with this.

Long before getting to the airport, you risk having one or both tickets/reservations cancelled due to the double booking.

If this is business travel, your employer should pay whatever fare is needed for the NYC trip. They should also pay the costs of having to change your approved vacation travel due to the business obligation.

+1, MSP is correct, plus even if you weren't checking a bag and somehow were able to get down to MCO (system didn't catch duplicate reservations-unlikely) your MCO-DTW reservation for sure would be canceled because you didn't show up for the first half of THAT reservation, DTW-MCO.

Thank you both. I will make it work without double booking.

Not so fast. Make the second reservation something like "extra seat." People do it all the time (especially POS or for a musical instrument). So in essence you get three seats for two of you from DTW to MCO.

Check w. your employer before engaging in shenanigans. There are many which figure that if you will sc*ew a vendor (DL in this case), you would do the same to them. As others note, if this is business travel, it's a routine cost of doing business. Happens all the time. Life goes on.