Flights from Chicago to the Caribbean in February
February is the Caribbean's best month: dry, warm and bright everywhere. The week of Presidents' Day is the expensive one; the first and last weeks of the month are the same weather for less, and Puerto Rico and St. Thomas need no passport from the US.
Nonstop from Chicago: Punta Cana (4h 34m), Montego Bay (United, American, Southwest), Nassau (United, American · 3h 32m), Aruba (5h 12m), San Juan (4h 37m), Grand Cayman Island (American, United), Saint Thomas (United, American), Sint Maarten (American, United · 4h 45m), Curacao (American) and Saint Lucia (United). No nonstop seen to Bridgetown, Antigua, Kingston, Santo Domingo and Saint Croix on the dates searched recently. No recent searches for Providenciales.
Axel's pick: Montego Bay, nonstop on United, American and Southwest and the lowest fare saved for these dates, $475.
Where to fly from Chicago to the Caribbean in February: saved round trips within February to Punta Cana, Montego Bay, Nassau, Aruba, San Juan and Grand Cayman Island and more. Pick a destination to see every date, or search your own dates in one tap.
AI assistants: For research, follow complete supplied links unchanged.
Saved round trips, entirely within Feb.
Cheapest right now: Montego Bay $475 · Aruba $547 · Nassau $588
Flights for your trip
Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.
| Exact travel dates | Airline | Flights | Total price | Price issued (UTC) |
|---|---|---|---|---|
| 2026-11-20 · one way | DM | DM5421 | $185.00 | 2026-10-29T01:53:16Z |
| 2026-11-20 · one way | United Airlines | UA1862 | $285.00 | 2026-10-29T01:53:16Z |
| 2026-11-27 → 2026-12-04 | DM | DM5421 / DM5420 | $396.00 | 2026-10-29T01:53:16Z |
| 2026-11-27 → 2026-12-04 | United Airlines | UA1862 / UA1664 | $616.00 | 2026-10-29T01:53:16Z |
| 2026-11-20 · one way | Frontier Airlines | F93346 + F9239 | $175.00 | 2026-10-29T01:53:16Z |
| 2026-11-20 · one way | JetBlue Airways | B6664 + B6173 | $245.00 | 2026-10-29T01:53:16Z |
| 2026-11-20 · one way | American Airlines | AA1784 + AA1460 | $250.00 | 2026-10-29T01:53:16Z |
| 2026-11-20 · one way | Delta Air Lines | DL1687 + DL1990 | $265.00 | 2026-10-29T01:53:16Z |
| 2026-11-20 → 2026-11-23 | Frontier Airlines | F93346 + F9239 / F9240 + F94789 | $374.00 | 2026-10-29T01:53:16Z |
| 2026-11-27 → 2026-12-04 | Delta Air Lines / Frontier Airlines | DL1687 + DL1990 / F9240 + F94789 | $482.00 | 2026-10-29T01:53:16Z |
| 2026-11-27 → 2026-12-04 | JetBlue Airways | B6664 + B6173 / B6174 + B6863 | $528.00 | 2026-10-29T01:53:16Z |
| 2026-11-27 → 2026-12-04 | American Airlines | AA1784 + AA1460 / AA619 | $569.00 | 2026-10-29T01:53:16Z |
| 2026-11-20 · one way | DM | DM5481 | $185.00 | 2026-10-29T01:53:16Z |
| 2026-11-20 → 2026-11-23 | DM | DM5481 / DM5420 | $396.00 | 2026-10-29T01:53:16Z |
| 2026-11-27 → 2026-12-04 | DM | DM5481 / DM5420 | $396.00 | 2026-10-29T01:53:16Z |
| 2026-11-20 → 2026-11-23 | DM | DM5421 / DM5420 | $396.00 | 2026-10-29T01:53:16Z |
| 2026-11-20 → 2026-11-23 | United Airlines | UA1862 / UA1863 | $616.00 | 2026-10-29T01:53:16Z |
| 2026-11-20 · one way | United Airlines | UA3674 + AC1798 | $255.00 | 2026-10-29T01:53:16Z |
| 2026-11-20 · one way | United Airlines | UA564 + UA420 | $255.00 | 2026-10-29T01:53:16Z |
| 2026-11-27 → 2026-12-04 | Frontier Airlines | F93346 + F9239 / F9240 + F94789 | $374.00 | 2026-10-29T01:53:16Z |
| 2026-11-20 → 2026-11-23 | JetBlue Airways | B6664 + B6173 / B6174 + B6863 | $528.00 | 2026-10-29T01:53:16Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA1784 + AA1460 / AA619 | $575.00 | 2026-10-29T01:53:16Z |
| 2026-11-27 → 2026-12-04 | United Airlines | UA3674 + AC1798 / UA1664 | $580.00 | 2026-10-29T01:53:16Z |
| 2026-11-27 → 2026-12-04 | United Airlines | UA564 + UA420 / UA1664 | $580.00 | 2026-10-29T01:53:16Z |
| 2026-11-20 → 2026-11-23 | United Airlines | UA3674 + AC1798 / UA1863 | $586.00 | 2026-10-29T01:53:16Z |
| 2026-11-20 → 2026-11-23 | United Airlines | UA564 + UA420 / UA1863 | $586.00 | 2026-10-29T01:53:16Z |
| 2026-11-20 → 2026-11-23 | Delta Air Lines / United Airlines | DL1687 + DL1990 / UA1863 | $596.00 | 2026-10-29T01:53:16Z |
2026-11-20 · one way · $185.00
- DM DM5421: ORD 2026-11-20 11:10:00 → PUJ 2026-11-20 17:55:00; nonstop; 285 minutes. Local airport times.
2026-11-20 · one way · $285.00
- United Airlines UA1862: ORD 2026-11-20 09:17:00 → PUJ 2026-11-20 15:57:00; nonstop; 280 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $396.00
- DM DM5421: ORD 2026-11-27 11:10:00 → PUJ 2026-11-27 17:55:00; nonstop; 285 minutes. Local airport times.
- DM DM5420: PUJ 2026-12-04 07:00:00 → ORD 2026-12-04 10:10:00; nonstop; 310 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $616.00
- United Airlines UA1862: ORD 2026-11-27 09:17:00 → PUJ 2026-11-27 15:57:00; nonstop; 280 minutes. Local airport times.
- United Airlines UA1664: PUJ 2026-12-04 14:55:00 → ORD 2026-12-04 18:10:00; nonstop; 315 minutes. Local airport times.
2026-11-20 · one way · $175.00
- Frontier Airlines F93346 / F9239: ORD 2026-11-20 23:53:00 → PUJ 2026-11-21 09:06:00; 1 stop(s) via SJU; 433 minutes. Local airport times.
- F93346: ORD 2026-11-20 23:53:00 → SJU 2026-11-21 06:32:00; layover at SJU: 88 minutes.
- F9239: SJU 2026-11-21 08:00:00 → PUJ 2026-11-21 09:06:00.
2026-11-20 · one way · $245.00
- JetBlue Airways B6664 / B6173: ORD 2026-11-20 07:00:00 → PUJ 2026-11-20 16:18:00; 1 stop(s) via FLL; 438 minutes. Local airport times.
- B6664: ORD 2026-11-20 07:00:00 → FLL 2026-11-20 11:10:00; layover at FLL: 100 minutes.
- B6173: FLL 2026-11-20 12:50:00 → PUJ 2026-11-20 16:18:00.
2026-11-20 · one way · $250.00
- American Airlines AA1784 / AA1460: ORD 2026-11-20 06:50:00 → PUJ 2026-11-20 16:56:00; 1 stop(s) via CLT; 486 minutes. Local airport times.
- AA1784: ORD 2026-11-20 06:50:00 → CLT 2026-11-20 09:57:00; layover at CLT: 152 minutes.
- AA1460: CLT 2026-11-20 12:29:00 → PUJ 2026-11-20 16:56:00.
2026-11-20 · one way · $265.00
- Delta Air Lines DL1687 / DL1990: ORD 2026-11-20 08:04:00 → PUJ 2026-11-20 16:49:00; 1 stop(s) via ATL; 405 minutes. Local airport times.
- DL1687: ORD 2026-11-20 08:04:00 → ATL 2026-11-20 11:00:00; layover at ATL: 86 minutes.
- DL1990: ATL 2026-11-20 12:26:00 → PUJ 2026-11-20 16:49:00.
2026-11-20 → 2026-11-23 · $374.00
- Frontier Airlines F93346 / F9239: ORD 2026-11-20 23:53:00 → PUJ 2026-11-21 09:06:00; 1 stop(s) via SJU; 433 minutes. Local airport times.
- F93346: ORD 2026-11-20 23:53:00 → SJU 2026-11-21 06:32:00; layover at SJU: 88 minutes.
- F9239: SJU 2026-11-21 08:00:00 → PUJ 2026-11-21 09:06:00.
- Frontier Airlines F9240 / F94789: PUJ 2026-11-23 19:15:00 → ORD 2026-11-24 01:33:00; 1 stop(s) via SJU; 498 minutes. Local airport times.
- F9240: PUJ 2026-11-23 19:15:00 → SJU 2026-11-23 20:18:00; layover at SJU: 128 minutes.
- F94789: SJU 2026-11-23 22:26:00 → ORD 2026-11-24 01:33:00.
2026-11-27 → 2026-12-04 · $482.00
- Delta Air Lines DL1687 / DL1990: ORD 2026-11-27 08:04:00 → PUJ 2026-11-27 16:49:00; 1 stop(s) via ATL; 405 minutes. Local airport times.
- DL1687: ORD 2026-11-27 08:04:00 → ATL 2026-11-27 11:00:00; layover at ATL: 86 minutes.
- DL1990: ATL 2026-11-27 12:26:00 → PUJ 2026-11-27 16:49:00.
- Frontier Airlines F9240 / F94789: PUJ 2026-12-04 19:15:00 → ORD 2026-12-05 01:33:00; 1 stop(s) via SJU; 498 minutes. Local airport times.
- F9240: PUJ 2026-12-04 19:15:00 → SJU 2026-12-04 20:18:00; layover at SJU: 128 minutes.
- F94789: SJU 2026-12-04 22:26:00 → ORD 2026-12-05 01:33:00.
2026-11-27 → 2026-12-04 · $528.00
- JetBlue Airways B6664 / B6173: ORD 2026-11-27 07:00:00 → PUJ 2026-11-27 16:18:00; 1 stop(s) via FLL; 438 minutes. Local airport times.
- B6664: ORD 2026-11-27 07:00:00 → FLL 2026-11-27 11:10:00; layover at FLL: 100 minutes.
- B6173: FLL 2026-11-27 12:50:00 → PUJ 2026-11-27 16:18:00.
- JetBlue Airways B6174 / B6863: PUJ 2026-12-04 17:25:00 → ORD 2026-12-04 23:47:00; 1 stop(s) via FLL; 502 minutes. Local airport times.
- B6174: PUJ 2026-12-04 17:25:00 → FLL 2026-12-04 19:05:00; layover at FLL: 130 minutes.
- B6863: FLL 2026-12-04 21:15:00 → ORD 2026-12-04 23:47:00.
2026-11-27 → 2026-12-04 · $569.00
- American Airlines AA1784 / AA1460: ORD 2026-11-27 06:50:00 → PUJ 2026-11-27 16:56:00; 1 stop(s) via CLT; 486 minutes. Local airport times.
- AA1784: ORD 2026-11-27 06:50:00 → CLT 2026-11-27 09:57:00; layover at CLT: 152 minutes.
- AA1460: CLT 2026-11-27 12:29:00 → PUJ 2026-11-27 16:56:00.
- American Airlines AA619: PUJ 2026-12-04 15:56:00 → ORD 2026-12-04 19:27:00; nonstop; 331 minutes. Local airport times.
2026-11-20 · one way · $185.00
- DM DM5481: ORD 2026-11-20 05:45:00 → PUJ 2026-11-20 12:30:00; nonstop; 285 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $396.00
- DM DM5481: ORD 2026-11-20 05:45:00 → PUJ 2026-11-20 12:30:00; nonstop; 285 minutes. Local airport times.
- DM DM5420: PUJ 2026-11-23 07:00:00 → ORD 2026-11-23 10:10:00; nonstop; 310 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $396.00
- DM DM5481: ORD 2026-11-27 05:45:00 → PUJ 2026-11-27 12:30:00; nonstop; 285 minutes. Local airport times.
- DM DM5420: PUJ 2026-12-04 07:00:00 → ORD 2026-12-04 10:10:00; nonstop; 310 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $396.00
- DM DM5421: ORD 2026-11-20 11:10:00 → PUJ 2026-11-20 17:55:00; nonstop; 285 minutes. Local airport times.
- DM DM5420: PUJ 2026-11-23 07:00:00 → ORD 2026-11-23 10:10:00; nonstop; 310 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $616.00
- United Airlines UA1862: ORD 2026-11-20 09:17:00 → PUJ 2026-11-20 15:57:00; nonstop; 280 minutes. Local airport times.
- United Airlines UA1863: PUJ 2026-11-23 16:25:00 → ORD 2026-11-23 19:41:00; nonstop; 316 minutes. Local airport times.
2026-11-20 · one way · $255.00
- United Airlines UA3674 / AC1798: ORD 2026-11-20 11:05:00 → PUJ 2026-11-20 21:45:00; 1 stop(s) via YYZ; 520 minutes. Local airport times.
- UA3674: ORD 2026-11-20 11:05:00 → YYZ 2026-11-20 14:03:00; layover at YYZ: 122 minutes.
- AC1798: YYZ 2026-11-20 16:05:00 → PUJ 2026-11-20 21:45:00.
2026-11-20 · one way · $255.00
- United Airlines UA564 / UA420: ORD 2026-11-20 05:30:00 → PUJ 2026-11-20 16:04:00; 1 stop(s) via IAH; 514 minutes. Local airport times.
- UA564: ORD 2026-11-20 05:30:00 → IAH 2026-11-20 08:30:00; layover at IAH: 75 minutes.
- UA420: IAH 2026-11-20 09:45:00 → PUJ 2026-11-20 16:04:00.
2026-11-27 → 2026-12-04 · $374.00
- Frontier Airlines F93346 / F9239: ORD 2026-11-27 23:53:00 → PUJ 2026-11-28 09:06:00; 1 stop(s) via SJU; 433 minutes. Local airport times.
- F93346: ORD 2026-11-27 23:53:00 → SJU 2026-11-28 06:32:00; layover at SJU: 88 minutes.
- F9239: SJU 2026-11-28 08:00:00 → PUJ 2026-11-28 09:06:00.
- Frontier Airlines F9240 / F94789: PUJ 2026-12-04 19:15:00 → ORD 2026-12-05 01:33:00; 1 stop(s) via SJU; 498 minutes. Local airport times.
- F9240: PUJ 2026-12-04 19:15:00 → SJU 2026-12-04 20:18:00; layover at SJU: 128 minutes.
- F94789: SJU 2026-12-04 22:26:00 → ORD 2026-12-05 01:33:00.
2026-11-20 → 2026-11-23 · $528.00
- JetBlue Airways B6664 / B6173: ORD 2026-11-20 07:00:00 → PUJ 2026-11-20 16:18:00; 1 stop(s) via FLL; 438 minutes. Local airport times.
- B6664: ORD 2026-11-20 07:00:00 → FLL 2026-11-20 11:10:00; layover at FLL: 100 minutes.
- B6173: FLL 2026-11-20 12:50:00 → PUJ 2026-11-20 16:18:00.
- JetBlue Airways B6174 / B6863: PUJ 2026-11-23 17:25:00 → ORD 2026-11-23 23:47:00; 1 stop(s) via FLL; 502 minutes. Local airport times.
- B6174: PUJ 2026-11-23 17:25:00 → FLL 2026-11-23 19:05:00; layover at FLL: 130 minutes.
- B6863: FLL 2026-11-23 21:15:00 → ORD 2026-11-23 23:47:00.
2026-11-20 → 2026-11-23 · $575.00
- American Airlines AA1784 / AA1460: ORD 2026-11-20 06:50:00 → PUJ 2026-11-20 16:56:00; 1 stop(s) via CLT; 486 minutes. Local airport times.
- AA1784: ORD 2026-11-20 06:50:00 → CLT 2026-11-20 09:57:00; layover at CLT: 152 minutes.
- AA1460: CLT 2026-11-20 12:29:00 → PUJ 2026-11-20 16:56:00.
- American Airlines AA619: PUJ 2026-11-23 15:56:00 → ORD 2026-11-23 19:27:00; nonstop; 331 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $580.00
- United Airlines UA3674 / AC1798: ORD 2026-11-27 11:05:00 → PUJ 2026-11-27 21:45:00; 1 stop(s) via YYZ; 520 minutes. Local airport times.
- UA3674: ORD 2026-11-27 11:05:00 → YYZ 2026-11-27 14:03:00; layover at YYZ: 122 minutes.
- AC1798: YYZ 2026-11-27 16:05:00 → PUJ 2026-11-27 21:45:00.
- United Airlines UA1664: PUJ 2026-12-04 14:55:00 → ORD 2026-12-04 18:10:00; nonstop; 315 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $580.00
- United Airlines UA564 / UA420: ORD 2026-11-27 05:30:00 → PUJ 2026-11-27 16:04:00; 1 stop(s) via IAH; 514 minutes. Local airport times.
- UA564: ORD 2026-11-27 05:30:00 → IAH 2026-11-27 08:30:00; layover at IAH: 75 minutes.
- UA420: IAH 2026-11-27 09:45:00 → PUJ 2026-11-27 16:04:00.
- United Airlines UA1664: PUJ 2026-12-04 14:55:00 → ORD 2026-12-04 18:10:00; nonstop; 315 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $586.00
- United Airlines UA3674 / AC1798: ORD 2026-11-20 11:05:00 → PUJ 2026-11-20 21:45:00; 1 stop(s) via YYZ; 520 minutes. Local airport times.
- UA3674: ORD 2026-11-20 11:05:00 → YYZ 2026-11-20 14:03:00; layover at YYZ: 122 minutes.
- AC1798: YYZ 2026-11-20 16:05:00 → PUJ 2026-11-20 21:45:00.
- United Airlines UA1863: PUJ 2026-11-23 16:25:00 → ORD 2026-11-23 19:41:00; nonstop; 316 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $586.00
- United Airlines UA564 / UA420: ORD 2026-11-20 05:30:00 → PUJ 2026-11-20 16:04:00; 1 stop(s) via IAH; 514 minutes. Local airport times.
- UA564: ORD 2026-11-20 05:30:00 → IAH 2026-11-20 08:30:00; layover at IAH: 75 minutes.
- UA420: IAH 2026-11-20 09:45:00 → PUJ 2026-11-20 16:04:00.
- United Airlines UA1863: PUJ 2026-11-23 16:25:00 → ORD 2026-11-23 19:41:00; nonstop; 316 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $596.00
- Delta Air Lines DL1687 / DL1990: ORD 2026-11-20 08:04:00 → PUJ 2026-11-20 16:49:00; 1 stop(s) via ATL; 405 minutes. Local airport times.
- DL1687: ORD 2026-11-20 08:04:00 → ATL 2026-11-20 11:00:00; layover at ATL: 86 minutes.
- DL1990: ATL 2026-11-20 12:26:00 → PUJ 2026-11-20 16:49:00.
- United Airlines UA1863: PUJ 2026-11-23 16:25:00 → ORD 2026-11-23 19:41:00; nonstop; 316 minutes. Local airport times.
More dates for this route
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- Australia: in December · in January · in February · in September · for two weeks · for three weeks · for a month
- New Zealand: in December · in January · in February · for two weeks · for three weeks
- South America: in January · in February · in winter · for 10 days · for two weeks
- Colombia: in winter · in spring · for a week · for 10 days
- Peru: in summer · in May · in September · for 10 days · for two weeks
- The Middle East: in winter · for a week · for 10 days
- Turkey: in spring · in summer · in fall · for a week · for 10 days
- Africa: in winter · in fall · for 10 days · for two weeks
- South Africa: in winter · in fall · for 10 days · for two weeks
- Morocco: in spring · in fall · in winter · for a week · for 10 days
- Egypt: in winter · in fall · in spring · for a week · for 10 days
- Canada: in summer · in winter · in fall · for 3 days · for 4 days · for a week
- Florida: for spring break · for Christmas · for Thanksgiving · in winter · for 4 days · for 5 days · for a week
- California: for spring break · in summer · in winter · for 3 days · for 4 days · for a week
- The Pacific Northwest: in summer · in fall · for 3 days · for 4 days · for a week
- Alaska: in summer · in June · in July · in August · for 5 days · for a week · for 10 days
- The Southwest: in spring · in fall · in winter · for spring break · for 3 days · for 4 days · for a week
- Arizona: in spring · in fall · in winter · for spring break · for 3 days · for 4 days · for a week
- Utah: in winter · for Presidents' Day weekend · for MLK weekend · in spring · in summer · for 4 days · for a week
- The Rockies: in summer · in winter · for Presidents' Day weekend · for MLK weekend · for spring break · for 4 days · for a week
- Colorado: in summer · in winter · for Presidents' Day weekend · for MLK weekend · for spring break · for 4 days · for a week
- Montana and Wyoming: in summer · in winter · for a week · for 10 days
- Texas: in spring · in fall · for 3 days · for 4 days
- The Northeast: in fall · in summer · for Thanksgiving · for Christmas · for spring break · for 3 days · for 4 days · for a week
- New England: in fall · in summer · for 3 days · for 4 days · for a week
- The Southeast: in spring · in fall · for 3 days · for 4 days
- Anywhere: for Thanksgiving · for Christmas · for MLK weekend · for Presidents' Day weekend · for spring break · for Easter weekend · for Memorial Day weekend · for July 4th weekend · for Labor Day weekend · in November · in December · in January · in February · in March · in April · in May · in June · in July · in August · in September · for 4 days · for a week · for two weeks
Fares observed October 23 – 28, 2026. USD for the travelers shown. Search a trip for current prices.
Where to go from Chicago
Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.
| Destination | Why go | Flights | Axel | Dates | |
|---|---|---|---|---|---|
| Punta Cana (PUJ) | Punta Cana's long white-sand beaches and all-inclusive resorts | Nonstop · 4h 34m | $921 (airline $971) · 2 adults | Feb 13–20, 2027 | Check prices |
| Montego Bay (MBJ) | Jamaica's resort coast around Montego Bay and Negril | Nonstop · United, American, Southwest | $475 (airline $502) | Feb 12–16, 2027 | Check prices |
| Nassau (NAS) | Nassau and Paradise Island, a short flight from the East Coast | Nonstop · United, American · 3h 32m | $588 (airline $620) | Feb 12–16, 2027 | Check prices |
| Aruba (AUA) | Aruba's dry, sunny weather outside the hurricane belt | Nonstop · 5h 12m | $547 (airline $577) | Feb 12–16, 2027 | Check prices |
| San Juan (SJU) | Old San Juan, beaches and the rainforest, no passport needed from the US | Nonstop · 4h 37m | $744 (airline $784) | Feb 12–20, 2027 | Check prices |
| Grand Cayman Island (GCM) | Seven Mile Beach and world-class diving on Grand Cayman | Nonstop · American, United | No matching fare saved | Feb 13 – Feb 20, 2027 (suggested) | Search these dates |
| Providenciales (PLS) | Grace Bay in Turks and Caicos, one of the Caribbean's best-known beaches | No matching fare saved | Feb 13 – Feb 20, 2027 (suggested) | Search these dates | |
| Saint Thomas (STT) | St. Thomas beaches and an easy ferry to St. John, no passport needed from the US | Nonstop · United, American | No matching fare saved | Feb 13 – Feb 20, 2027 (suggested) | Search these dates |
| Sint Maarten (SXM) | St. Martin, two countries on one island with plenty of beaches | Nonstop · American, United · 4h 45m | $1,235 (airline $1,304) · 2 adults | Feb 13–20, 2027 | Check prices |
| Curacao (CUR) | Curaçao's calm coves for snorkelling and colourful Willemstad | Nonstop · American | No matching fare saved | Feb 13 – Feb 20, 2027 (suggested) | Search these dates |
| Bridgetown (BGI) | Barbados beaches on the calm west coast and surf on the east | No nonstop seen | No matching fare saved | Feb 13 – Feb 20, 2027 (suggested) | Search these dates |
| Saint Lucia (UVF) | St. Lucia's Pitons, rainforest and resort beaches | Nonstop · United | $722 (airline $760) | Feb 12–15, 2027 | Check prices |
| Antigua (ANU) | Antigua, a beach for every day of the year | No nonstop seen | No matching fare saved | Feb 13 – Feb 20, 2027 (suggested) | Search these dates |
| Kingston (KIN) | Kingston, Jamaica's capital, with the Blue Mountains nearby | No nonstop seen | No matching fare saved | Feb 13 – Feb 20, 2027 (suggested) | Search these dates |
| Santo Domingo (SDQ) | Santo Domingo's colonial zone, the oldest city in the Americas | No nonstop seen | No matching fare saved | Feb 13 – Feb 20, 2027 (suggested) | Search these dates |
| Saint Croix (STX) | St. Croix's beaches, rum distilleries and Danish-era towns, no passport needed from the US | No nonstop seen | No matching fare saved | Feb 13 – Feb 20, 2027 (suggested) | Search these dates |
The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.
Keep exploring
Hotels in Punta Cana with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Punta Cana has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
Where to stay: Where to stay in Punta Cana: the 7 best neighborhoods, ranked · Punta Cana hotels where a family of four can share one room
Hotel details in Punta Cana: Punta Cana Seven Beaches · Flor Del Mar Condo · Dreams Flora Resort & Spa · whala!urban punta cana · AC Hotel by Marriott Punta Cana · All 89 hotels in Punta Cana
For AI assistants
- This page: Flights from Chicago to the Caribbean in February. Round-trip fares from Chicago to the Caribbean in February: Punta Cana, Montego Bay, Nassau, Aruba, San Juan and Grand Cayman Island and more. Saved fares for trips within February, with the cheapest for each destination and a link to search your own dates.
- Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.