It depends on what kind of vacation your looking for I go to D.R all the time for air fare hotel and rental for about $700 - $750 usd but now spending money is a different thing If you want more info send me a message.

have you considered traveling to PUERTO RICO ? IT’S A BREEZE TO TRAVEL TO …NO PASSPORT NEEDED. IF YOU STAY IN CONDADO YOU CAN PROBABLY GET A GOOD DEAL THERE ARE PLENTY OF LOCAL RESTAURANTS NO NEED FOR AN ALL INCLUSIVE THE CORAL PRINCESS IN HAS A DECENT CONTINENTAL BREAKFAST INCLUDED IN THERE ROOM RATE. JETBLUE AIRWAYS HAS SOME REALLY GOOD DEAL FROM YOUR AREA TO SAN JUAN. JUST SOMETHING TO CONSIDER. HERE ARE SOME WEBSITES FOR YOU TO EXPLORE, I BOOKED (EVERYTHING MYSELF) A 20 DAY TRIP FOR FROM CHICAGO, TRAVELING IN SEPTEMBER FOR $2,200.00. THAT INCLUDED ALL LODGING COSTS, CAR RENAL, AROUND-TRIP NON-STOP AIRFARE ON AA AND ALL TAXES. IF YOU NEED HELP PLANNING A PUERTO RICO VACATION CONTACT ME BY CLICKING ON MY I-CON. I AM NOT A TRAVEL AGENT JUST SOME ONE WHO LIKES TO TRAVEL.
(PUERTO RICO FORUMS)

Have you tried Orbitz? There is a link from the page below. I’ve also put info page for om Rep which has links which may help.

try….I am going to Punta Cana end of Sept. and all inclusive for 7 days…..just $689! Have been to the DR with Apple previously and they make it so easy, even have a rep at the hotel…I’m not affiliated with them nor are they paying me…was just happy with their services and am using them again.

The DR is not exactly the party capital of the Caribbean, so if that is what you are really looking for I would have to suggest searching further. The cheapest area is Punta Cana, I was thr in Nov 05. The area is very under-developed. Our Hotel had a mountain in the front, ocean in the back and bush land ALL around! It was interesting to say the least, but I wasn’t expecting it! The resorts provide excellent entertainment, so thr really isn’t too much need to go elsewhere ecspecially if you are paying all -inclusive. I know closer to Santo Domingo thr’s a lot of nite life, but it’s @ least 1 1/2 hrs from Punta Cana on bumpy roads.

The trick to getting cheap getaways is holding off until a month before and looking for the ‘last minute deals’ I really stick with Applevacations.com or Funjet.com
All of the vacations I have been on in the past couple years have been under $700 PP all inclusive that includes the flight, the transfers, the food and the drink for 7 days! I am from the midwest, so you should have some deals that are close to what we get here, ecspecially being on the East coast, I see sweet deals from thr all the time! Good luck and enjoy!

check flight/hotel deals on orbitz.com, travelocity.com, expedia.com