My goal is to be on the island of Saba before classes start in January, 2005.
*All fares gathered via www.orbitz.com
**some airport codes: CVG(cincinnati), MIA(miami), MCO(orlando), DAY(dayton), SXM(st_marten), SKB(st_kitts, nevis), SAB(saba), SJU(san_juanPR), ORD(chicago), LEX(lexingtonKY),FLL(fort_lauderdale)
***All fares one traveler, one way, depart anytime

Finding a good fare can be time consuming, and one must be flexible to get the best price. I am using a variety of conditions and submitting the results here.

First set of variables,
CVG to SXM
did not widen airport search

Dec18 $703 (CVG->BOS->ATL->SXM)
Dec19 $704 (CVG->MIA->SXM)
Dec20 $653 (CVG->ORD->SJU->SXM)
Dec21 $653 (CVG->ORD->SJU->SXM)
Dec22 $679 (CVG->MCO->SJU->SXM)
Dec23 $659 (CVG->ORD->SJU->SXM)
Dec24 $703 (CVG->BOS->ATL->SXM)
Dec25 $658 (CVG->ORD->SJU->SXM)
Dec26 $653 (CVG->ORD->SJU->SXM)
Dec27 $659 (CVG->ORD->SJU->SXM)
Dec28 $653 (CVG->ORD->SJU->SXM)
Dec29 $653 (CVG->ORD->SJU->SXM)
Dec30 $653 (CVG->ORD->SJU->SXM)
Dec31 $653 (CVG->ORD->SJU->SXM)
Jan01 $653 (CVG->ORD->SJU->SXM)
Jan02 $653 (CVG->ORD->SJU->SXM)
Jan03 $653 (CVG->ORD->SJU->SXM)
Jan04 $653 (CVG->ORD->SJU->SXM)
Jan05 $653 (CVG->ORD->SJU->SXM)

Second set,
CVG (+ airports within 70miles) to SXM (+70mi)

Dec18 $703 (CVG->MCO->SJU->SKB)
Dec19 $380 (DAY->ATL->FLL->SKB)
Dec20 $643 (CVG->ORD->SJU->SXM)
Dec21 $643 (LEX->ORD->SJU->SXM)
Dec22 $346 (DAY->ATL->FLL->SKB)
Dec23 $659 (LEX->ORD->SJU->SXM)
Dec24 $703 (CVG->SDF->ATL->SXM)
Dec25 $648 (LEX->ORD->SJU->SXM)
Dec26 $463 (DAY->ATL->FLL->SKB)
Dec27 $649 (CVG->ORD->SJU->SXM)
Dec28 $643 (LEX->ORD->SJU->SXM)
Dec29 $346 (DAY->ATL->FLL->SKB)
Dec30 $643 (LEX->ORD->SJU->SXM)
Dec31 $643 (CVG->ORD->SJU->SXM)
Jan01 $643 (LEX->ORD->SJU->SXM)
Jan02 $380 (DAY->ATL->FLL->SKB)
Jan03 $649 (DAY->ATL->FLL->SKB)
Jan04 $634 (DAY->ATL->FLL->SKB)
Jan05 $317 (DAY->ATL->FLL->SKB)

(these are the lowest prices but you still need a connecting flight from St. Kitts to Saba for ~$100? I don't know what winair pricing is.)

Third set,
CVG to SAB (should've done this first, I suppose)
did not widen airport search

Dec18 $784 (CVG->SDF->ATL->SXM->SAB)
Dec19 $786 (CVG->ATL->SXM->SAB)
Dec20 $742 (CVG->ORD->SJU->SXM->SAB)
Dec21 $742 (CVG->ORD->SJU->SXM->SAB)
Dec22 $766 (CVG->MCO->SJU->SXM->SAB)
Dec23 $742 (CVG->ORD->SJU->SXM->SAB)
Dec24 $784 (CVG->SDF->ATL->SXM->SAB)
Dec25 $747 (CVG->ORD->SJU->SXM->SAB)
Dec26 $742 (CVG->ORD->SJU->SXM->SAB)
Dec27 $742 (CVG->ORD->SJU->SXM->SAB)
Dec28 $742 (CVG->ORD->SJU->SXM->SAB)
Dec29 $717 (CVG->CLT->SXM->SAB)
Dec30 $742 (CVG->ORD->SJU->SXM->SAB)
Dec31 $742 (CVG->ORD->SJU->SXM->SAB)
Jan01 $722 (CVG->PHL->SXM->SAB)
Jan02 $742 (CVG->ORD->SJU->SXM->SAB)
Jan03 $742 (CVG->ORD->SJU->SXM->SAB)
Jan04 $742 (CVG->ATL->SJU->SXM->SAB)
Jan05 $742 (CVG->ORD->SJU->SXM->SAB)

Fourth set,
CVG (+70mi.) to SAB (+70mi.)

Dec18 $703 (CVG->BNA->ATL->SXM)
Dec19 $380 (DAY->ATL->FLL->SKB)
Dec20 $643 (LEX->ORD->SJU->SXM)
Dec21 $643 (LEX->ORD->SJU->SXM)
Dec22 $346 (DAY->ATL->FLL->SKB)
Dec23 $649 (LEX->ORD->SJU->SXM)
Dec24 $703 (CVG->SDF->ATL->SXM)
Dec25 $648 (LEX->ORD->SJU->SXM)
Dec26 $463 (DAY->ATL->FLL->SKB)
Dec27 $649 (LEX->ORD->SJU->SXM)
Dec28 $643 (LEX->ORD->SJU->SXM)
Dec29 $346 (DAY->ATL->FLL->SKB)
Dec30 $643 (LEX->ORD->SJU->SXM)
Dec31 $643 (LEX->ORD->SJU->SXM)
Jan01 $643 (LEX->ORD->SJU->SXM)
Jan02 $380 (DAY->ATL->FLL->SKB)
Jan03 $643 (LEX->ORD->SJU->SXM)
Jan04 $634 (LEX->ORD->SJU->SXM)
Jan05 $317 (DAY->ATL->FLL->SKB)

Fifth set, last,
CVG (+70mi.) to SAB

Dec18 $777 (DAY->ATL->JFK->SXM->SAB)
Dec19 $786 (CVG->MIA->SXM->SAB)
Dec20 $737 (LEX->ORD->SJU->SXM->SAB)
Dec21 $742 (DAY->ORD->SJU->SXM->SAB)
Dec22 $766 (CVG->MCO->SJU->SXM->SAB)
Dec23 $742 (CVG->ORD->SJU->SXM->SAB)
Dec24 $786 (CVG->ATL->SXM->SAB)
Dec25 $737 (LEX->ORD->SJU->SXM->SAB)
Dec26 $742 (DAY->ORD->SJU->SXM->SAB)
Dec27 $742 (CVG->ORD->SJU->SXM->SAB)
Dec28 $737 (LEX->ORD->SJU->SXM->SAB)
Dec29 $717 (CVG->CLT->SXM->SAB)
Dec30 $742 (CVG->ORD->SJU->SXM->SAB)
Dec31 $737 (LEX->ORD->SJU->SXM->SAB)
Jan01 $695 (DAY->ATL->PHL->SXM->SAB)
Jan02 $737 (LEX->ORD->SJU->SXM->SAB)
Jan03 $737 (LEX->ORD->SJU->SXM->SAB)
Jan04 $737 (LEX->ORD->SJU->SXM->SAB)
Jan05 $737 (LEX->ORD->SJU->SXM->SAB)

Lastly, WinAir connecting flights from St. Maarten to Saba will cost from $80-$120 I think. Someone can verify Winward Air's prices.