We live north of Detroit, and fly AA from DTW to SXM, with a connection in Charlotte, N.C. This year our February flight cost $1032/ pp round trip, which we purchased in late August. Plus $14.95 pp for an aisle seat each flight. Total $2195 for the two of us. The year after Covid, we waited until September to book and our flight cost $1150 pp. I am always so envious of the people who live on the East Coast and have direct flights, or at least much lower prices.
When we first purchased our Time Share in 1995, there was a direct flight from DTW to SXM on Travel Charter, a weekly charter flight during the winter months, which could include a package deal with hotel, or just the flight. We flew with them for perhaps 8 or 9 years, and then the company shut down its flights from DTW. Our only choice then was either Delta or AA, and Delta is always quite a bit more expensive from DTW to anywhere in the Caribbean.