Toronto or Buffalo to Santo Domingo

Only charters fly direct from Toronto......however....

Air Canada does have their 'vacation' package flights which usually start in Dec. but as far as I know they only go to Punta Cana.
We flew Air Canada to Miami -then codeshare AA to SD on Thursday for a very reasonable price.
There are direct flights from Buffalo (sorry I don't know which airline but the price in Dec. was $384US plus taxes).

You can try Air Transat,Skyservice websites to see charter availability and prices or you can go to HumeTravel.com and do a search with dates to see what comes up!

direct flights

try Westjet

There are charters seasonally that begin on Dec 15, direct to SDQ. They leave once a week, and you can book to return 1 or 2 weeks after departure. check www.selloffvacations.com:

and go where it says "Santo Domingo" to check dates and prices

I checked Departing dec 15, returning the 22, comes to about $580 taxes included
returning one week later cost $875. If you don't mind a little busing to get to Santo Domingo, you can always fly direct to POP or Punta Cana via west jet, and take a bus. I recently got a ticket from ottawa direct to punta cana for $500 taxes included off selloffvacations, travelling with westjet.