Award flights from Chicago O’Hare (ORD) to the Caribbean
AwardTool saw award space on 6 routes from Chicago O’Hare (ORD) to the Caribbean in the last 30 days, into 6 airports in 6 countries, on 12 programs. Lowest business class observed: 15,000 points + $26.60, Chicago O’Hare (ORD) to Nassau (NAS), with Alaska Atmos Rewards.
Prices observed – .
Page regenerated from the Oct 16, 2026 data snapshot (normally daily). Summary last changed . Seats change quickly.
- Routes with award space
- 6
- Countries reached
- 6
- Lowest business class
- 15,000 points + $26.60
- ORD–NAS · Atmos
- Lowest economy
- 7,500 points + $26.60
- ORD–NAS · Atmos
- Lowest first class
- 35,000 points + $26.60
- ORD–NAS · Atmos
Award routes from Chicago O’Hare (ORD) to the Caribbean by destination country
Countries by number of routes, with the lowest awards AwardTool saw on 2 or more dates on their routes.
| Destination country | Routes | Lowest business | Lowest economy |
|---|---|---|---|
| Aruba | 1 | 27,500 miles + $15.60ORD–AUA · AAdvantage | 10,000 miles + $15.60ORD–AUA · AAdvantage |
| Bahamas | 1 | 15,000 points + $26.60ORD–NAS · Atmos | 7,500 points + $26.60ORD–NAS · Atmos |
| Cayman Islands | 1 | 66,200 miles + taxes varyORD–GCM · Smiles · nonstop | 12,500 points + $25.60ORD–GCM · Atmos |
| Dominican Republic | 1 | 25,000 points + $75.52ORD–PUJ · Atmos | 8,500 miles + $55.52ORD–PUJ · SkyMiles |
| Jamaica | 1 | — | 19,000 points + $72.70ORD–MBJ · Velocity |
| Turks and Caicos Islands | 1 | 58,400 miles + taxes not reportedORD–PLS · Smiles · Mixed cabin | 19,000 points + $40.92ORD–PLS · Velocity |
Award routes from Chicago O’Hare (ORD) to the Caribbean
The lowest one-way award AwardTool observed on each route, by cabin, with the program and the number of dates seen. Flights within the Caribbean are not counted here.
| Route | Economy | Business | First | Nonstop seen | Programs |
|---|---|---|---|---|---|
| Chicago O’Hare (ORD) to Aruba (AUA) | 10,000 miles + $15.60AAdvantage · 76 dates | 27,500 miles + $15.60AAdvantage · 72 dates | — | Yes | 3 |
| Chicago O’Hare (ORD) to Grand Cayman (GCM) | 12,500 points + $25.60Atmos · 291 dates | 25,000 points + $25.60Atmos · 1 date | 35,000 points + $25.60Atmos · 163 dates | Yes | 3 |
| Chicago O’Hare (ORD) to Montego Bay (MBJ) | 19,000 points + $72.70Velocity · 115 dates | — | — | Yes | 1 |
| Chicago O’Hare (ORD) to Nassau (NAS) | 7,500 points + $26.60Atmos · 299 dates | 15,000 points + $26.60Atmos · 14 dates | 35,000 points + $26.60Atmos · 270 dates | Yes | 1 |
| Chicago O’Hare (ORD) to Providenciales (PLS) | 19,000 points + $40.92Velocity · 130 dates | 37,500 points + $40.92Velocity · 1 date | — | Yes | 2 |
| Chicago O’Hare (ORD) to Punta Cana (PUJ) | 8,500 miles + $55.52SkyMiles · 325 dates | 25,000 points + $75.52Atmos · 11 dates | 35,000 points + $75.52Atmos · 195 dates | Yes | 9 |
Prices are one-way per traveler: the program's points or miles plus taxes and carrier fees in USD, as AwardTool observed them in the observation window. Award space changes constantly. A seat we saw may be gone, and space we haven't seen may exist. Always confirm with a live search before transferring points; most transfers can't be reversed.
Lowest awards by month from Chicago O’Hare (ORD) to the Caribbean
The lowest one-way award AwardTool observed for departures in each month across every route on this page, with its route and program and the number of routes with award space that month. Counting only month prices from programs with award space on 2 or more dates that month, and leaving out unusually low outliers.
| Month | Economy | Premium Economy | Business | First |
|---|---|---|---|---|
| 10,000 milesORD–AUA · AAdvantage · 6 routes | 23,061 pointsORD–PUJ · Aeroplan · 2 routes | 25,000 pointsORD–PUJ · Atmos · 4 routes | 35,000 pointsORD–NAS · Atmos · 2 routes | |
| 8,500 milesORD–PUJ · SkyMiles · 6 routes | 23,061 pointsORD–PUJ · Aeroplan · 2 routes | 25,000 pointsORD–PUJ · Atmos · 4 routes | 35,000 pointsORD–GCM · Atmos · 3 routes | |
| 7,500 pointsORD–NAS · Atmos · 6 routes | 23,061 pointsORD–PUJ · Aeroplan · 2 routes | 15,000 pointsORD–NAS · Atmos · 5 routes | 35,000 pointsORD–GCM · Atmos · 3 routes | |
| 7,500 pointsORD–NAS · Atmos · 6 routes | 23,061 pointsORD–PUJ · Aeroplan · 2 routes | 15,000 pointsORD–NAS · Atmos · 5 routes | 35,000 pointsORD–GCM · Atmos · 3 routes | |
| 7,500 pointsORD–NAS · Atmos · 6 routes | 116,462 pointsORD–PUJ · Aeroplan · 2 routes | 28,826 pointsORD–PUJ · Aeroplan · 5 routes | 35,000 pointsORD–GCM · Atmos · 3 routes | |
| 7,500 pointsORD–NAS · Atmos · 6 routes | 73,451 pointsORD–PUJ · Aeroplan · 2 routes | 27,500 milesORD–AUA · AAdvantage · 4 routes | 35,000 pointsORD–GCM · Atmos · 3 routes | |
| 7,500 pointsORD–NAS · Atmos · 6 routes | 23,061 pointsORD–PUJ · Aeroplan · 1 route | 27,500 milesORD–AUA · AAdvantage · 4 routes | 35,000 pointsORD–GCM · Atmos · 3 routes | |
| 7,500 pointsORD–NAS · Atmos · 6 routes | — | 35,000 pointsORD–PUJ · Aeroplan · 4 routes | 35,000 pointsORD–GCM · Atmos · 3 routes | |
| 7,500 pointsORD–NAS · Atmos · 6 routes | — | 15,000 pointsORD–NAS · Atmos · 5 routes | 35,000 pointsORD–GCM · Atmos · 3 routes | |
| 7,500 pointsORD–NAS · Atmos · 6 routes | — | 35,000 pointsORD–PUJ · Aeroplan · 4 routes | 35,000 pointsORD–GCM · Atmos · 3 routes | |
| 7,500 pointsORD–NAS · Atmos · 6 routes | — | 35,000 pointsORD–PUJ · Aeroplan · 4 routes | 35,000 pointsORD–GCM · Atmos · 3 routes | |
| 12,500 pointsORD–PUJ · Atmos · 6 routes | — | 35,000 pointsORD–PUJ · Aeroplan · 4 routes | 35,000 pointsORD–GCM · Atmos · 3 routes |
Taxes vary by route and program and are not part of these month figures; each route page shows them.
Programs with award space from Chicago O’Hare (ORD) to the Caribbean
Programs by number of routes, with the lowest award each showed on 2 or more dates.
| Program | Routes | Lowest business | Lowest economy |
|---|---|---|---|
| GOL Smiles | 4 | 66,200 miles + taxes varyORD–GCM · Smiles · nonstop | 30,900 miles + taxes not reportedORD–GCM · Smiles |
| Alaska Atmos Rewards | 3 | 15,000 points + $26.60ORD–NAS · Atmos | 7,500 points + $26.60ORD–NAS · Atmos |
| Virgin Australia Velocity | 3 | — | 19,000 points + $40.92ORD–PLS · Velocity |
| American Airlines AAdvantage | 1 | 27,500 miles + $15.60ORD–AUA · AAdvantage | 10,000 miles + $15.60ORD–AUA · AAdvantage |
| Air Canada Aeroplan | 1 | 28,825 points + $136.73ORD–PUJ · Aeroplan · Mixed cabin | 14,413 points + $125.63ORD–PUJ · Aeroplan |
| Avianca LifeMiles | 1 | 30,000 miles + $58.00ORD–PUJ · LifeMiles | 15,000 miles + $78.92ORD–PUJ · LifeMiles |
| Delta SkyMiles | 1 | — | 8,500 miles + $55.52ORD–PUJ · SkyMiles |
| Etihad Guest | 1 | 40,000 miles + $83.42ORD–PUJ · Etihad Guest | 23,000 miles + $83.42ORD–PUJ · Etihad Guest |
| Air France/KLM Flying Blue | 1 | 51,000 miles + $87.92ORD–PUJ · Flying Blue | 19,000 miles + $87.92ORD–PUJ · Flying Blue |
| Qantas Frequent Flyer | 1 | 43,600 points + $39.00ORD–AUA · Qantas | 20,700 points + $39.00ORD–AUA · Qantas |
| United MileagePlus | 1 | 42,200 miles + taxes varyORD–PUJ · MileagePlus · nonstop | 16,700 miles + $55.52ORD–PUJ · MileagePlus |
| Virgin Atlantic Flying Club | 1 | — | 26,000 points + $55.52ORD–PUJ · Virgin Atlantic |
Transferable points to the Caribbean
Banks whose points transfer to programs with award space to the Caribbean, with the points each award takes at the listed ratio.
Questions about award flights from Chicago O’Hare (ORD) to the Caribbean
What's the lowest business-class award from Chicago O’Hare (ORD) to the Caribbean AwardTool has seen?
15,000 points + $26.60, Chicago O’Hare (ORD) to Nassau (NAS), with Alaska Atmos Rewards, which showed business-class award space on that route on 14 departure dates in the last 30 days. Search live before you transfer points.
What's the lowest economy award from Chicago O’Hare (ORD) to the Caribbean AwardTool has seen?
7,500 points + $26.60, Chicago O’Hare (ORD) to Nassau (NAS), with Alaska Atmos Rewards, which showed economy award space on that route on 299 departure dates in the last 30 days. Search live before you transfer points.
Which countries in the Caribbean had award space from Chicago O’Hare (ORD)?
Aruba, Bahamas, Cayman Islands, Dominican Republic, Jamaica and Turks and Caicos Islands, counting published routes with award space in the last 30 days.
Which airports in the Caribbean had award space from Chicago O’Hare (ORD)?
Aruba (AUA), Grand Cayman (GCM), Montego Bay (MBJ), Nassau (NAS), Providenciales (PLS) and Punta Cana (PUJ), in the last 30 days. Only routes where a program showed award space on 2 or more dates are listed.
When were business-class awards from Chicago O’Hare (ORD) to the Caribbean lowest?
Departures in Dec 2026: 15,000 points ORD to NAS with Alaska Atmos Rewards, open on 7 dates that month. Counting only month prices from programs with award space on 2 or more dates that month, and leaving out unusually low outliers. A record of what AwardTool observed, not a forecast.
Which programs had award space from Chicago O’Hare (ORD) to the Caribbean?
GOL Smiles (4 routes), Alaska Atmos Rewards (3 routes), Virgin Australia Velocity (3 routes), American Airlines AAdvantage (1 route), Air Canada Aeroplan (1 route), Avianca LifeMiles (1 route) and 6 other programs. GOL Smiles had the most routes.