Flights from Milwaukee to the Caribbean for 5 days
Five days is a resort stay with one day out: Punta Cana or Montego Bay for all-inclusives, San Juan for a city with beaches, Aruba for the surest sun. Fly nonstop; an island worth a connection needs the full week.
One stop via Philadelphia: Aruba. No nonstop seen to Montego Bay, Nassau, San Juan, Grand Cayman Island, Providenciales, Saint Thomas, Sint Maarten, Curacao, Bridgetown, Saint Lucia, Antigua, Kingston, Santo Domingo and Saint Croix on the dates searched recently. No recent searches for Punta Cana.
Where to fly from Milwaukee to the Caribbean for 5 days: round trips of 4 to 5 nights 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 for Five days in December (Dec 3 – Dec 7, 2026) and Five days in March (Mar 4 – Mar 8, 2027).
Cheapest right now: Aruba $650 · Antigua $860 · Bridgetown $868
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 | Southwest Airlines | WN3100 + WN782 | $285.00 | 2026-10-29T01:30:23Z |
| 2026-11-20 · one way | American Airlines | AA4365 + AA539 | $305.00 | 2026-10-29T01:30:23Z |
| 2026-11-20 · one way | Delta Air Lines | DL1221 + DL1990 | $325.00 | 2026-10-29T01:30:23Z |
| 2026-11-27 → 2026-12-04 | Southwest Airlines | WN3939 + WN811 / WN783 + WN2814 | $599.50 | 2026-10-29T01:30:23Z |
| 2026-11-27 → 2026-12-04 | American Airlines | AA4365 + AA539 / AA619 + AA4992 | $643.10 | 2026-10-29T01:30:23Z |
| 2026-11-20 → 2026-11-23 | Delta Air Lines / American Airlines | DL1221 + DL1990 / AA619 + AA4992 | $663.10 | 2026-10-29T01:30:23Z |
| 2026-11-20 · one way | Southwest Airlines | WN3939 + WN811 | $285.00 | 2026-10-29T01:30:23Z |
| 2026-11-20 · one way | American Airlines | AA1479 + AA1625 | $305.00 | 2026-10-29T01:30:23Z |
| 2026-11-20 · one way | Delta Air Lines | DL4074 + DL1979 | $325.00 | 2026-10-29T01:30:23Z |
| 2026-11-27 → 2026-12-04 | Southwest Airlines | WN3100 + WN782 / WN783 + WN2814 | $599.50 | 2026-10-29T01:30:23Z |
| 2026-11-20 → 2026-11-23 | Southwest Airlines | WN3100 + WN782 / WN783 + WN2814 | $599.50 | 2026-10-29T01:30:23Z |
| 2026-11-20 → 2026-11-23 | Southwest Airlines | WN3939 + WN811 / WN783 + WN2814 | $599.50 | 2026-10-29T01:30:23Z |
| 2026-11-27 → 2026-12-04 | American Airlines | AA1479 + AA1625 / AA619 + AA4992 | $643.10 | 2026-10-29T01:30:23Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA1479 + AA1625 / AA619 + AA4992 | $643.10 | 2026-10-29T01:30:23Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA4365 + AA539 / AA619 + AA4992 | $643.10 | 2026-10-29T01:30:23Z |
| 2026-11-20 → 2026-11-23 | Delta Air Lines / American Airlines | DL4074 + DL1979 / AA619 + AA4992 | $663.10 | 2026-10-29T01:30:23Z |
| 2026-11-27 → 2026-12-04 | Delta Air Lines / American Airlines | DL4074 + DL1979 / AA619 + AA4992 | $666.70 | 2026-10-29T01:30:23Z |
| 2026-11-27 → 2026-12-04 | Delta Air Lines / American Airlines | DL1221 + DL1990 / AA619 + AA4992 | $666.70 | 2026-10-29T01:30:23Z |
2026-11-20 · one way · $285.00
- Southwest Airlines WN3100 / WN782: MKE 2026-11-20 05:55:00 → PUJ 2026-11-20 15:50:00; 1 stop(s) via MCO; 475 minutes. Local airport times.
- WN3100: MKE 2026-11-20 05:55:00 → MCO 2026-11-20 09:50:00; layover at MCO: 140 minutes.
- WN782: MCO 2026-11-20 12:10:00 → PUJ 2026-11-20 15:50:00.
2026-11-20 · one way · $305.00
- American Airlines AA4365 / AA539: MKE 2026-11-20 06:29:00 → PUJ 2026-11-20 18:13:00; 1 stop(s) via MIA; 584 minutes. Local airport times.
- AA4365: MKE 2026-11-20 06:29:00 → MIA 2026-11-20 11:10:00; layover at MIA: 216 minutes.
- AA539: MIA 2026-11-20 14:46:00 → PUJ 2026-11-20 18:13:00.
2026-11-20 · one way · $325.00
- Delta Air Lines DL1221 / DL1990: MKE 2026-11-20 05:30:00 → PUJ 2026-11-20 16:49:00; 1 stop(s) via ATL; 559 minutes. Local airport times.
- DL1221: MKE 2026-11-20 05:30:00 → ATL 2026-11-20 08:39:00; layover at ATL: 227 minutes.
- DL1990: ATL 2026-11-20 12:26:00 → PUJ 2026-11-20 16:49:00.
2026-11-27 → 2026-12-04 · $599.50
- Southwest Airlines WN3939 / WN811: MKE 2026-11-27 06:35:00 → PUJ 2026-11-27 16:00:00; 1 stop(s) via BWI; 445 minutes. Local airport times.
- WN3939: MKE 2026-11-27 06:35:00 → BWI 2026-11-27 09:30:00; layover at BWI: 100 minutes.
- WN811: BWI 2026-11-27 11:10:00 → PUJ 2026-11-27 16:00:00.
- Southwest Airlines WN783 / WN2814: PUJ 2026-12-04 13:50:00 → MKE 2026-12-04 21:05:00; 1 stop(s) via MCO; 555 minutes. Local airport times.
- WN783: PUJ 2026-12-04 13:50:00 → MCO 2026-12-04 15:40:00; layover at MCO: 205 minutes.
- WN2814: MCO 2026-12-04 19:05:00 → MKE 2026-12-04 21:05:00.
2026-11-27 → 2026-12-04 · $643.10
- American Airlines AA4365 / AA539: MKE 2026-11-27 06:29:00 → PUJ 2026-11-27 18:13:00; 1 stop(s) via MIA; 584 minutes. Local airport times.
- AA4365: MKE 2026-11-27 06:29:00 → MIA 2026-11-27 11:10:00; layover at MIA: 216 minutes.
- AA539: MIA 2026-11-27 14:46:00 → PUJ 2026-11-27 18:13:00.
- American Airlines AA619 / AA4992: PUJ 2026-12-04 15:56:00 → MKE 2026-12-04 22:37:00; 1 stop(s) via ORD; 521 minutes. Local airport times.
- AA619: PUJ 2026-12-04 15:56:00 → ORD 2026-12-04 19:27:00; layover at ORD: 128 minutes.
- AA4992: ORD 2026-12-04 21:35:00 → MKE 2026-12-04 22:37:00.
2026-11-20 → 2026-11-23 · $663.10
- Delta Air Lines DL1221 / DL1990: MKE 2026-11-20 05:30:00 → PUJ 2026-11-20 16:49:00; 1 stop(s) via ATL; 559 minutes. Local airport times.
- DL1221: MKE 2026-11-20 05:30:00 → ATL 2026-11-20 08:39:00; layover at ATL: 227 minutes.
- DL1990: ATL 2026-11-20 12:26:00 → PUJ 2026-11-20 16:49:00.
- American Airlines AA619 / AA4992: PUJ 2026-11-23 15:56:00 → MKE 2026-11-23 22:37:00; 1 stop(s) via ORD; 521 minutes. Local airport times.
- AA619: PUJ 2026-11-23 15:56:00 → ORD 2026-11-23 19:27:00; layover at ORD: 128 minutes.
- AA4992: ORD 2026-11-23 21:35:00 → MKE 2026-11-23 22:37:00.
2026-11-20 · one way · $285.00
- Southwest Airlines WN3939 / WN811: MKE 2026-11-20 06:35:00 → PUJ 2026-11-20 16:00:00; 1 stop(s) via BWI; 445 minutes. Local airport times.
- WN3939: MKE 2026-11-20 06:35:00 → BWI 2026-11-20 09:30:00; layover at BWI: 100 minutes.
- WN811: BWI 2026-11-20 11:10:00 → PUJ 2026-11-20 16:00:00.
2026-11-20 · one way · $305.00
- American Airlines AA1479 / AA1625: MKE 2026-11-20 07:17:00 → PUJ 2026-11-20 16:21:00; 1 stop(s) via CLT; 424 minutes. Local airport times.
- AA1479: MKE 2026-11-20 07:17:00 → CLT 2026-11-20 10:30:00; layover at CLT: 81 minutes.
- AA1625: CLT 2026-11-20 11:51:00 → PUJ 2026-11-20 16:21:00.
2026-11-20 · one way · $325.00
- Delta Air Lines DL4074 / DL1979: MKE 2026-11-20 06:24:00 → PUJ 2026-11-20 17:30:00; 1 stop(s) via MSP; 546 minutes. Local airport times.
- DL4074: MKE 2026-11-20 06:24:00 → MSP 2026-11-20 07:56:00; layover at MSP: 139 minutes.
- DL1979: MSP 2026-11-20 10:15:00 → PUJ 2026-11-20 17:30:00.
2026-11-27 → 2026-12-04 · $599.50
- Southwest Airlines WN3100 / WN782: MKE 2026-11-27 05:55:00 → PUJ 2026-11-27 15:50:00; 1 stop(s) via MCO; 475 minutes. Local airport times.
- WN3100: MKE 2026-11-27 05:55:00 → MCO 2026-11-27 09:50:00; layover at MCO: 140 minutes.
- WN782: MCO 2026-11-27 12:10:00 → PUJ 2026-11-27 15:50:00.
- Southwest Airlines WN783 / WN2814: PUJ 2026-12-04 13:50:00 → MKE 2026-12-04 21:05:00; 1 stop(s) via MCO; 555 minutes. Local airport times.
- WN783: PUJ 2026-12-04 13:50:00 → MCO 2026-12-04 15:40:00; layover at MCO: 205 minutes.
- WN2814: MCO 2026-12-04 19:05:00 → MKE 2026-12-04 21:05:00.
2026-11-20 → 2026-11-23 · $599.50
- Southwest Airlines WN3100 / WN782: MKE 2026-11-20 05:55:00 → PUJ 2026-11-20 15:50:00; 1 stop(s) via MCO; 475 minutes. Local airport times.
- WN3100: MKE 2026-11-20 05:55:00 → MCO 2026-11-20 09:50:00; layover at MCO: 140 minutes.
- WN782: MCO 2026-11-20 12:10:00 → PUJ 2026-11-20 15:50:00.
- Southwest Airlines WN783 / WN2814: PUJ 2026-11-23 13:50:00 → MKE 2026-11-23 21:05:00; 1 stop(s) via MCO; 555 minutes. Local airport times.
- WN783: PUJ 2026-11-23 13:50:00 → MCO 2026-11-23 15:40:00; layover at MCO: 205 minutes.
- WN2814: MCO 2026-11-23 19:05:00 → MKE 2026-11-23 21:05:00.
2026-11-20 → 2026-11-23 · $599.50
- Southwest Airlines WN3939 / WN811: MKE 2026-11-20 06:35:00 → PUJ 2026-11-20 16:00:00; 1 stop(s) via BWI; 445 minutes. Local airport times.
- WN3939: MKE 2026-11-20 06:35:00 → BWI 2026-11-20 09:30:00; layover at BWI: 100 minutes.
- WN811: BWI 2026-11-20 11:10:00 → PUJ 2026-11-20 16:00:00.
- Southwest Airlines WN783 / WN2814: PUJ 2026-11-23 13:50:00 → MKE 2026-11-23 21:05:00; 1 stop(s) via MCO; 555 minutes. Local airport times.
- WN783: PUJ 2026-11-23 13:50:00 → MCO 2026-11-23 15:40:00; layover at MCO: 205 minutes.
- WN2814: MCO 2026-11-23 19:05:00 → MKE 2026-11-23 21:05:00.
2026-11-27 → 2026-12-04 · $643.10
- American Airlines AA1479 / AA1625: MKE 2026-11-27 07:17:00 → PUJ 2026-11-27 16:21:00; 1 stop(s) via CLT; 424 minutes. Local airport times.
- AA1479: MKE 2026-11-27 07:17:00 → CLT 2026-11-27 10:30:00; layover at CLT: 81 minutes.
- AA1625: CLT 2026-11-27 11:51:00 → PUJ 2026-11-27 16:21:00.
- American Airlines AA619 / AA4992: PUJ 2026-12-04 15:56:00 → MKE 2026-12-04 22:37:00; 1 stop(s) via ORD; 521 minutes. Local airport times.
- AA619: PUJ 2026-12-04 15:56:00 → ORD 2026-12-04 19:27:00; layover at ORD: 128 minutes.
- AA4992: ORD 2026-12-04 21:35:00 → MKE 2026-12-04 22:37:00.
2026-11-20 → 2026-11-23 · $643.10
- American Airlines AA1479 / AA1625: MKE 2026-11-20 07:17:00 → PUJ 2026-11-20 16:21:00; 1 stop(s) via CLT; 424 minutes. Local airport times.
- AA1479: MKE 2026-11-20 07:17:00 → CLT 2026-11-20 10:30:00; layover at CLT: 81 minutes.
- AA1625: CLT 2026-11-20 11:51:00 → PUJ 2026-11-20 16:21:00.
- American Airlines AA619 / AA4992: PUJ 2026-11-23 15:56:00 → MKE 2026-11-23 22:37:00; 1 stop(s) via ORD; 521 minutes. Local airport times.
- AA619: PUJ 2026-11-23 15:56:00 → ORD 2026-11-23 19:27:00; layover at ORD: 128 minutes.
- AA4992: ORD 2026-11-23 21:35:00 → MKE 2026-11-23 22:37:00.
2026-11-20 → 2026-11-23 · $643.10
- American Airlines AA4365 / AA539: MKE 2026-11-20 06:29:00 → PUJ 2026-11-20 18:13:00; 1 stop(s) via MIA; 584 minutes. Local airport times.
- AA4365: MKE 2026-11-20 06:29:00 → MIA 2026-11-20 11:10:00; layover at MIA: 216 minutes.
- AA539: MIA 2026-11-20 14:46:00 → PUJ 2026-11-20 18:13:00.
- American Airlines AA619 / AA4992: PUJ 2026-11-23 15:56:00 → MKE 2026-11-23 22:37:00; 1 stop(s) via ORD; 521 minutes. Local airport times.
- AA619: PUJ 2026-11-23 15:56:00 → ORD 2026-11-23 19:27:00; layover at ORD: 128 minutes.
- AA4992: ORD 2026-11-23 21:35:00 → MKE 2026-11-23 22:37:00.
2026-11-20 → 2026-11-23 · $663.10
- Delta Air Lines DL4074 / DL1979: MKE 2026-11-20 06:24:00 → PUJ 2026-11-20 17:30:00; 1 stop(s) via MSP; 546 minutes. Local airport times.
- DL4074: MKE 2026-11-20 06:24:00 → MSP 2026-11-20 07:56:00; layover at MSP: 139 minutes.
- DL1979: MSP 2026-11-20 10:15:00 → PUJ 2026-11-20 17:30:00.
- American Airlines AA619 / AA4992: PUJ 2026-11-23 15:56:00 → MKE 2026-11-23 22:37:00; 1 stop(s) via ORD; 521 minutes. Local airport times.
- AA619: PUJ 2026-11-23 15:56:00 → ORD 2026-11-23 19:27:00; layover at ORD: 128 minutes.
- AA4992: ORD 2026-11-23 21:35:00 → MKE 2026-11-23 22:37:00.
2026-11-27 → 2026-12-04 · $666.70
- Delta Air Lines DL4074 / DL1979: MKE 2026-11-27 06:24:00 → PUJ 2026-11-27 17:30:00; 1 stop(s) via MSP; 546 minutes. Local airport times.
- DL4074: MKE 2026-11-27 06:24:00 → MSP 2026-11-27 07:56:00; layover at MSP: 139 minutes.
- DL1979: MSP 2026-11-27 10:15:00 → PUJ 2026-11-27 17:30:00.
- American Airlines AA619 / AA4992: PUJ 2026-12-04 15:56:00 → MKE 2026-12-04 22:37:00; 1 stop(s) via ORD; 521 minutes. Local airport times.
- AA619: PUJ 2026-12-04 15:56:00 → ORD 2026-12-04 19:27:00; layover at ORD: 128 minutes.
- AA4992: ORD 2026-12-04 21:35:00 → MKE 2026-12-04 22:37:00.
2026-11-27 → 2026-12-04 · $666.70
- Delta Air Lines DL1221 / DL1990: MKE 2026-11-27 05:30:00 → PUJ 2026-11-27 16:49:00; 1 stop(s) via ATL; 559 minutes. Local airport times.
- DL1221: MKE 2026-11-27 05:30:00 → ATL 2026-11-27 08:39:00; layover at ATL: 227 minutes.
- DL1990: ATL 2026-11-27 12:26:00 → PUJ 2026-11-27 16:49:00.
- American Airlines AA619 / AA4992: PUJ 2026-12-04 15:56:00 → MKE 2026-12-04 22:37:00; 1 stop(s) via ORD; 521 minutes. Local airport times.
- AA619: PUJ 2026-12-04 15:56:00 → ORD 2026-12-04 19:27:00; layover at ORD: 128 minutes.
- AA4992: ORD 2026-12-04 21:35:00 → MKE 2026-12-04 22:37:00.
More dates for this route
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- Hawaii: for Christmas · for Thanksgiving · for spring break · for Presidents' Day weekend · in summer · for 4 days · for 5 days · for a week · for 10 days
- Mexico: for Christmas · for Thanksgiving · for spring break · for Presidents' Day weekend · for MLK weekend · in winter · in February · for 4 days · for 5 days · for a week
- The Caribbean: for Christmas · for spring break · for Presidents' Day weekend · in winter · in February · for 4 days · for a week
- Costa Rica: for Christmas · for spring break · in winter · for a week · for 10 days
- Central America: for Christmas · for spring break · in winter · for a week · for 10 days
- Europe: in summer · in May · in September · in December · for spring break · for Christmas · for a week · for 10 days · for two weeks
- Italy: in summer · in May · in June · in September · for Christmas · for a week · for 10 days · for two weeks
- Spain: in summer · in May · in September · for spring break · for a week · for 10 days
- Greece: in summer · in May · in June · in September · for a week · for 10 days · for two weeks
- Portugal: in summer · in May · in September · in winter · for 4 days · for a week · for 10 days
- Croatia: in summer · in June · in September · for a week · for 10 days
- Iceland: in summer · in winter · in September · for 4 days · for a week
- Scandinavia: in summer · in winter · in September · for 4 days · for a week · for 10 days
- Eastern Europe: in summer · in May · in September · in December · for a week · for 10 days
- England: in spring · in summer · in fall · for Christmas · for 4 days · for a week · for 10 days
- Scotland: in summer · in fall · for 4 days · for a week
- Ireland: in spring · in summer · in fall · for Christmas · for 4 days · for a week · for 10 days
- Japan: in April · in November · in winter · in summer · for a week · for 10 days · for two weeks
- Asia: in spring · in fall · in winter · for a week · for 10 days · for two weeks
- Southeast Asia: in winter · in November · in January · in February · for 10 days · for two weeks · for three weeks · for a month
- Thailand: in winter · in November · in January · in February · for 10 days · for two weeks · for three weeks
- Vietnam: in winter · in November · in February · in spring · for 10 days · for two weeks
- Bali: in summer · in winter · for 10 days · for two weeks · for a month
- India: in winter · in December · for two weeks · for a month
- 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 28, 2026. USD for the travelers shown. Search a trip for current prices.
Where to go from Milwaukee
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 | No matching fare saved | Dec 3 – Dec 7, 2026 (suggested) | Search these dates | |
| Montego Bay (MBJ) | Jamaica's resort coast around Montego Bay and Negril | No nonstop seen | No matching fare saved | Dec 3 – Dec 7, 2026 (suggested) | Search these dates |
| Nassau (NAS) | Nassau and Paradise Island, a short flight from the East Coast | No nonstop seen | No matching fare saved | Dec 3 – Dec 7, 2026 (suggested) | Search these dates |
| Aruba (AUA) | Aruba's dry, sunny weather outside the hurricane belt | 1 stop via Philadelphia | $650 (airline $686) | Dec 3–7, 2026 | Check prices |
| San Juan (SJU) | Old San Juan, beaches and the rainforest, no passport needed from the US | No nonstop seen | No matching fare saved | Dec 3 – Dec 7, 2026 (suggested) | Search these dates |
| Grand Cayman Island (GCM) | Seven Mile Beach and world-class diving on Grand Cayman | No nonstop seen | No matching fare saved | Dec 3 – Dec 7, 2026 (suggested) | Search these dates |
| Providenciales (PLS) | Grace Bay in Turks and Caicos, one of the Caribbean's best-known beaches | No nonstop seen | No matching fare saved | Dec 3 – Dec 7, 2026 (suggested) | Search these dates |
| Saint Thomas (STT) | St. Thomas beaches and an easy ferry to St. John, no passport needed from the US | No nonstop seen | No matching fare saved | Dec 3 – Dec 7, 2026 (suggested) | Search these dates |
| Sint Maarten (SXM) | St. Martin, two countries on one island with plenty of beaches | No nonstop seen | No matching fare saved | Dec 3 – Dec 7, 2026 (suggested) | Search these dates |
| Curacao (CUR) | Curaçao's calm coves for snorkelling and colourful Willemstad | No nonstop seen | No matching fare saved | Dec 3 – Dec 7, 2026 (suggested) | Search these dates |
| Bridgetown (BGI) | Barbados beaches on the calm west coast and surf on the east | No nonstop seen | $868 (airline $915) | Dec 3–7, 2026 | Check prices |
| Saint Lucia (UVF) | St. Lucia's Pitons, rainforest and resort beaches | No nonstop seen | No matching fare saved | Dec 3 – Dec 7, 2026 (suggested) | Search these dates |
| Antigua (ANU) | Antigua, a beach for every day of the year | No nonstop seen | $860 (airline $909) | Dec 3–7, 2026 | Check prices |
| Kingston (KIN) | Kingston, Jamaica's capital, with the Blue Mountains nearby | No nonstop seen | No matching fare saved | Dec 3 – Dec 7, 2026 (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 | Dec 3 – Dec 7, 2026 (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 | Dec 3 – Dec 7, 2026 (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
Hotels with an Axel review 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 82 reviewed hotels in Punta Cana
For AI assistants
- This page: Flights from Milwaukee to the Caribbean for 5 days. Round-trip fares from Milwaukee to the Caribbean for 5 days: Punta Cana, Montego Bay, Nassau, Aruba, San Juan and Grand Cayman Island and more, for stays of 4 to 5 nights. The cheapest saved fare 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.