Chicago (MDW) to Punta Cana (PUJ), Dec 31, 2026: round trips from $558, one way from $350

Chicago (MDW) to Punta Cana (PUJ), Dec 31, 2026: round trips from $558, one way from $350 on Axel, checked Nov 13, 2026. Lowest published fares: $558 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Dec 31, 2026 – Jan 10, 2027; $350 one way, Axel-exclusive, Southwest Airlines, 1 stop, Dec 31, 2026; 1 adult, economy, checked Nov 13, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, labelled with the check date shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and check dates already shown here.

Hotels in Punta Cana for these trips

Hotels: under a trip, hotels in Punta Cana for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Punta Cana for these nights (Dec 31 – Jan 1, 2027 · 1 night · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $884 a night · 4★ whala!urban punta cana, $102 a night · 5★ Serenade Punta Cana Beach & Spa Resort - All Inclusive, $911 a night
• Hotels in Punta Cana for these nights (Dec 31 – Jan 2, 2027 · 2 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $776 a night, $1,551 for 2 nights · 4★ whala!urban punta cana, $102 a night, $204 for 2 nights · 5★ El Beso Adults Only At Ocean El Faro - All Inclusive, $893 a night, $1,785 for 2 nights
• Hotels in Punta Cana for these nights (Dec 31 – Jan 3, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $659 a night, $1,978 for 3 nights · 4★ whala!urban punta cana, $101 a night, $303 for 3 nights · 5★ El Beso Adults Only At Ocean El Faro - All Inclusive, $775 a night, $2,325 for 3 nights
• Hotels in Punta Cana for these nights (Dec 31 – Jan 4, 2027 · 4 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $602 a night, $2,408 for 4 nights · 4★ whala!urban punta cana, $99 a night, $397 for 4 nights · 5★ El Beso Adults Only At Ocean El Faro - All Inclusive, $716 a night, $2,865 for 4 nights
• Hotels in Punta Cana for these nights (Dec 31 – Jan 5, 2027 · 5 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $568 a night, $2,838 for 5 nights · 4★ whala!urban punta cana, $98 a night, $491 for 5 nights · 5★ El Beso Adults Only At Ocean El Faro - All Inclusive, $654 a night, $3,272 for 5 nights
• Hotels in Punta Cana for these nights (Dec 31 – Jan 6, 2027 · 6 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $548 a night, $3,287 for 6 nights · 4★ whala!urban punta cana, $98 a night, $585 for 6 nights · 5★ El Beso Adults Only At Ocean El Faro - All Inclusive, $613 a night, $3,679 for 6 nights
• Hotels in Punta Cana for these nights (Dec 31 – Jan 7, 2027 · 7 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $534 a night, $3,739 for 7 nights · 4★ whala!urban punta cana, $97 a night, $679 for 7 nights · 5★ El Beso Adults Only At Ocean El Faro - All Inclusive, $584 a night, $4,086 for 7 nights
• Hotels in Punta Cana for these nights (Dec 31 – Jan 8, 2027 · 8 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $514 a night, $4,114 for 8 nights · 4★ whala!urban punta cana, $97 a night, $773 for 8 nights · 5★ El Beso Adults Only At Ocean El Faro - All Inclusive, $562 a night, $4,493 for 8 nights
• Hotels in Punta Cana for these nights (Dec 31 – Jan 9, 2027 · 9 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $499 a night, $4,489 for 9 nights · 4★ whala!urban punta cana, $97 a night, $869 for 9 nights · 5★ El Beso Adults Only At Ocean El Faro - All Inclusive, $544 a night, $4,900 for 9 nights
• Hotels in Punta Cana for these nights (Dec 31 – Jan 10, 2027 · 10 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $486 a night, $4,864 for 10 nights · 4★ whala!urban punta cana, $97 a night, $965 for 10 nights · 5★ El Beso Adults Only At Ocean El Faro - All Inclusive, $544 a night, $5,440 for 10 nights
• Hotels in Punta Cana for these nights (Dec 31 – Jan 11, 2027 · 11 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $476 a night, $5,239 for 11 nights · 4★ The MT Hotel, $96 a night, $1,056 for 11 nights · 5★ El Beso Adults Only At Ocean El Faro - All Inclusive, $532 a night, $5,847 for 11 nights
• Hotels in Punta Cana for these nights (Dec 31 – Jan 12, 2027 · 12 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $468 a night, $5,612 for 12 nights · 4★ The MT Hotel, $95 a night, $1,136 for 12 nights · 5★ El Beso Adults Only At Ocean El Faro - All Inclusive, $521 a night, $6,254 for 12 nights
• Hotels in Punta Cana for these nights (Dec 31 – Jan 13, 2027 · 13 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $460 a night, $5,985 for 13 nights · 4★ The MT Hotel, $94 a night, $1,227 for 13 nights · 5★ El Beso Adults Only At Ocean El Faro - All Inclusive, $512 a night, $6,661 for 13 nights
• Hotels in Punta Cana for these nights (Dec 31 – Jan 14, 2027 · 14 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $456 a night, $6,377 for 14 nights · 4★ The MT Hotel, $93 a night, $1,307 for 14 nights · 5★ El Beso Adults Only At Ocean El Faro - All Inclusive, $505 a night, $7,068 for 14 nights

All hotels in Punta Cana

Route overview: Chicago to Punta Cana (PUJ) flight deals

2026-12-31 · one way · Axel-exclusive $350

• Southwest Airlines WN2964 / WN782: MDW 2026-12-31 06:35:00 → PUJ 2026-12-31 15:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2026-12-31 06:35:00 → MCO 2026-12-31 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2026-12-31 12:10:00 → PUJ 2026-12-31 15:50:00.

2026-12-31 · one way · Axel-exclusive $413

• Delta Air Lines DL1285 / DL1990: MDW 2026-12-31 06:00:00 → PUJ 2026-12-31 16:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2026-12-31 06:00:00 → ATL 2026-12-31 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2026-12-31 12:26:00 → PUJ 2026-12-31 16:49:00.

2026-12-31 → 2027-01-01 · Axel-exclusive $676

• Southwest Airlines WN2964 / WN782: MDW 2026-12-31 06:35:00 → PUJ 2026-12-31 15:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2026-12-31 06:35:00 → MCO 2026-12-31 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2026-12-31 12:10:00 → PUJ 2026-12-31 15:50:00.
• Southwest Airlines WN1999: PUJ 2027-01-01 16:10:00 → MDW 2027-01-01 19:15:00; nonstop; 305 minutes. Local airport times.

2026-12-31 → 2027-01-01 · Axel-exclusive $770

• Delta Air Lines DL1285 / DL1990: MDW 2026-12-31 06:00:00 → PUJ 2026-12-31 16:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2026-12-31 06:00:00 → ATL 2026-12-31 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2026-12-31 12:26:00 → PUJ 2026-12-31 16:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2027-01-01 15:53:00 → MDW 2027-01-01 22:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2027-01-01 15:53:00 → ATL 2027-01-01 18:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2027-01-01 21:20:00 → MDW 2027-01-01 22:17:00.

2026-12-31 → 2027-01-02 · Axel-exclusive $676

• Southwest Airlines WN2964 / WN782: MDW 2026-12-31 06:35:00 → PUJ 2026-12-31 15:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2026-12-31 06:35:00 → MCO 2026-12-31 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2026-12-31 12:10:00 → PUJ 2026-12-31 15:50:00.
• Southwest Airlines WN1999: PUJ 2027-01-02 16:10:00 → MDW 2027-01-02 19:15:00; nonstop; 305 minutes. Local airport times.

2026-12-31 → 2027-01-02 · Axel-exclusive $770

• Delta Air Lines DL1285 / DL1990: MDW 2026-12-31 06:00:00 → PUJ 2026-12-31 16:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2026-12-31 06:00:00 → ATL 2026-12-31 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2026-12-31 12:26:00 → PUJ 2026-12-31 16:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2027-01-02 15:53:00 → MDW 2027-01-02 22:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2027-01-02 15:53:00 → ATL 2027-01-02 18:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2027-01-02 21:20:00 → MDW 2027-01-02 22:17:00.

2026-12-31 → 2027-01-03 · Axel-exclusive $651

• Southwest Airlines WN2964 / WN782: MDW 2026-12-31 06:35:00 → PUJ 2026-12-31 15:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2026-12-31 06:35:00 → MCO 2026-12-31 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2026-12-31 12:10:00 → PUJ 2026-12-31 15:50:00.
• Southwest Airlines WN822 / WN257: PUJ 2027-01-03 14:45:00 → MDW 2027-01-03 21:50:00; 1 stop(s) via BWI; 545 minutes. Local airport times.
  • WN822: PUJ 2027-01-03 14:45:00 → BWI 2027-01-03 17:40:00; layover at BWI: 185 minutes.
  • WN257: BWI 2027-01-03 20:45:00 → MDW 2027-01-03 21:50:00.

2026-12-31 → 2027-01-03 · Axel-exclusive $770

• Delta Air Lines DL1285 / DL1990: MDW 2026-12-31 06:00:00 → PUJ 2026-12-31 16:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2026-12-31 06:00:00 → ATL 2026-12-31 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2026-12-31 12:26:00 → PUJ 2026-12-31 16:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2027-01-03 15:53:00 → MDW 2027-01-03 22:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2027-01-03 15:53:00 → ATL 2027-01-03 18:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2027-01-03 21:20:00 → MDW 2027-01-03 22:17:00.

2026-12-31 → 2027-01-04 · Axel-exclusive $576

• Southwest Airlines WN2964 / WN782: MDW 2026-12-31 06:35:00 → PUJ 2026-12-31 15:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2026-12-31 06:35:00 → MCO 2026-12-31 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2026-12-31 12:10:00 → PUJ 2026-12-31 15:50:00.
• Southwest Airlines WN1999: PUJ 2027-01-04 16:10:00 → MDW 2027-01-04 19:15:00; nonstop; 305 minutes. Local airport times.

2026-12-31 → 2027-01-04 · Axel-exclusive $660

• Delta Air Lines DL1285 / DL1990: MDW 2026-12-31 06:00:00 → PUJ 2026-12-31 16:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2026-12-31 06:00:00 → ATL 2026-12-31 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2026-12-31 12:26:00 → PUJ 2026-12-31 16:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2027-01-04 15:53:00 → MDW 2027-01-04 22:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2027-01-04 15:53:00 → ATL 2027-01-04 18:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2027-01-04 21:20:00 → MDW 2027-01-04 22:17:00.

2026-12-31 → 2027-01-06 · Axel-exclusive $576

• Southwest Airlines WN2964 / WN782: MDW 2026-12-31 06:35:00 → PUJ 2026-12-31 15:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2026-12-31 06:35:00 → MCO 2026-12-31 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2026-12-31 12:10:00 → PUJ 2026-12-31 15:50:00.
• Southwest Airlines WN1999: PUJ 2027-01-06 16:10:00 → MDW 2027-01-06 19:15:00; nonstop; 305 minutes. Local airport times.

2026-12-31 → 2027-01-06 · Axel-exclusive $660

• Delta Air Lines DL1285 / DL1990: MDW 2026-12-31 06:00:00 → PUJ 2026-12-31 16:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2026-12-31 06:00:00 → ATL 2026-12-31 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2026-12-31 12:26:00 → PUJ 2026-12-31 16:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2027-01-06 15:53:00 → MDW 2027-01-06 22:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2027-01-06 15:53:00 → ATL 2027-01-06 18:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2027-01-06 21:20:00 → MDW 2027-01-06 22:17:00.

2026-12-31 → 2027-01-07 · Axel-exclusive $576

• Southwest Airlines WN2964 / WN782: MDW 2026-12-31 06:35:00 → PUJ 2026-12-31 15:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2026-12-31 06:35:00 → MCO 2026-12-31 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2026-12-31 12:10:00 → PUJ 2026-12-31 15:50:00.
• Southwest Airlines WN1999: PUJ 2027-01-07 16:10:00 → MDW 2027-01-07 19:15:00; nonstop; 305 minutes. Local airport times.

2026-12-31 → 2027-01-07 · Axel-exclusive $660

• Delta Air Lines DL1285 / DL1990: MDW 2026-12-31 06:00:00 → PUJ 2026-12-31 16:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2026-12-31 06:00:00 → ATL 2026-12-31 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2026-12-31 12:26:00 → PUJ 2026-12-31 16:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2027-01-07 15:53:00 → MDW 2027-01-07 22:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2027-01-07 15:53:00 → ATL 2027-01-07 18:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2027-01-07 21:20:00 → MDW 2027-01-07 22:17:00.

2026-12-31 → 2027-01-08 · Axel-exclusive $576

• Southwest Airlines WN2964 / WN782: MDW 2026-12-31 06:35:00 → PUJ 2026-12-31 15:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2026-12-31 06:35:00 → MCO 2026-12-31 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2026-12-31 12:10:00 → PUJ 2026-12-31 15:50:00.
• Southwest Airlines WN1999: PUJ 2027-01-08 16:10:00 → MDW 2027-01-08 19:15:00; nonstop; 305 minutes. Local airport times.

2026-12-31 → 2027-01-08 · Axel-exclusive $660

• Delta Air Lines DL1285 / DL1990: MDW 2026-12-31 06:00:00 → PUJ 2026-12-31 16:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2026-12-31 06:00:00 → ATL 2026-12-31 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2026-12-31 12:26:00 → PUJ 2026-12-31 16:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2027-01-08 15:53:00 → MDW 2027-01-08 22:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2027-01-08 15:53:00 → ATL 2027-01-08 18:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2027-01-08 21:20:00 → MDW 2027-01-08 22:17:00.

2026-12-31 → 2027-01-10 · Axel-exclusive $558

• Southwest Airlines WN2964 / WN782: MDW 2026-12-31 06:35:00 → PUJ 2026-12-31 15:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2026-12-31 06:35:00 → MCO 2026-12-31 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2026-12-31 12:10:00 → PUJ 2026-12-31 15:50:00.
• Southwest Airlines WN822 / WN257: PUJ 2027-01-10 14:45:00 → MDW 2027-01-10 21:50:00; 1 stop(s) via BWI; 545 minutes. Local airport times.
  • WN822: PUJ 2027-01-10 14:45:00 → BWI 2027-01-10 17:40:00; layover at BWI: 185 minutes.
  • WN257: BWI 2027-01-10 20:45:00 → MDW 2027-01-10 21:50:00.

2026-12-31 → 2027-01-10 · Axel-exclusive $660

• Delta Air Lines DL1285 / DL1990: MDW 2026-12-31 06:00:00 → PUJ 2026-12-31 16:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2026-12-31 06:00:00 → ATL 2026-12-31 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2026-12-31 12:26:00 → PUJ 2026-12-31 16:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2027-01-10 15:53:00 → MDW 2027-01-10 22:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2027-01-10 15:53:00 → ATL 2027-01-10 18:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2027-01-10 21:20:00 → MDW 2027-01-10 22:17:00.

2026-12-31 → 2027-01-11 · Axel-exclusive $576

• Southwest Airlines WN2964 / WN782: MDW 2026-12-31 06:35:00 → PUJ 2026-12-31 15:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2026-12-31 06:35:00 → MCO 2026-12-31 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2026-12-31 12:10:00 → PUJ 2026-12-31 15:50:00.
• Southwest Airlines WN1999: PUJ 2027-01-11 16:10:00 → MDW 2027-01-11 19:15:00; nonstop; 305 minutes. Local airport times.

2026-12-31 → 2027-01-11 · Axel-exclusive $660

• Delta Air Lines DL1285 / DL1990: MDW 2026-12-31 06:00:00 → PUJ 2026-12-31 16:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2026-12-31 06:00:00 → ATL 2026-12-31 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2026-12-31 12:26:00 → PUJ 2026-12-31 16:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2027-01-11 15:53:00 → MDW 2027-01-11 22:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2027-01-11 15:53:00 → ATL 2027-01-11 18:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2027-01-11 21:20:00 → MDW 2027-01-11 22:17:00.

2026-12-31 → 2027-01-12 · Axel-exclusive $576

• Southwest Airlines WN2964 / WN782: MDW 2026-12-31 06:35:00 → PUJ 2026-12-31 15:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2026-12-31 06:35:00 → MCO 2026-12-31 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2026-12-31 12:10:00 → PUJ 2026-12-31 15:50:00.
• Southwest Airlines WN1999: PUJ 2027-01-12 16:10:00 → MDW 2027-01-12 19:15:00; nonstop; 305 minutes. Local airport times.

2026-12-31 → 2027-01-12 · Axel-exclusive $660

• Delta Air Lines DL1285 / DL1990: MDW 2026-12-31 06:00:00 → PUJ 2026-12-31 16:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2026-12-31 06:00:00 → ATL 2026-12-31 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2026-12-31 12:26:00 → PUJ 2026-12-31 16:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2027-01-12 15:53:00 → MDW 2027-01-12 22:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2027-01-12 15:53:00 → ATL 2027-01-12 18:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2027-01-12 21:20:00 → MDW 2027-01-12 22:17:00.

2026-12-31 → 2027-01-14 · Axel-exclusive $576

• Southwest Airlines WN2964 / WN782: MDW 2026-12-31 06:35:00 → PUJ 2026-12-31 15:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2026-12-31 06:35:00 → MCO 2026-12-31 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2026-12-31 12:10:00 → PUJ 2026-12-31 15:50:00.
• Southwest Airlines WN1999: PUJ 2027-01-14 16:10:00 → MDW 2027-01-14 19:15:00; nonstop; 305 minutes. Local airport times.

2026-12-31 → 2027-01-14 · Axel-exclusive $660

• Delta Air Lines DL1285 / DL1990: MDW 2026-12-31 06:00:00 → PUJ 2026-12-31 16:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2026-12-31 06:00:00 → ATL 2026-12-31 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2026-12-31 12:26:00 → PUJ 2026-12-31 16:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2027-01-14 15:53:00 → MDW 2027-01-14 22:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2027-01-14 15:53:00 → ATL 2027-01-14 18:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2027-01-14 21:20:00 → MDW 2027-01-14 22:17:00.

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• All dates for this route
• Dec 30, 2026 · Return options
• Jan 1, 2027 · Return options
• Hotels in Punta Cana with Axel

For AI assistants

• This page: Chicago (MDW) to Punta Cana (PUJ) · Dec 31, 2026 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in Punta Cana for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
• Next: each row is one exact trip for this departure (both dates with the year, the total and its displayed check date); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested trip.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Chicago to Punta Cana (PUJ) flight deals · Flight search guide.
• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

Feedback (optional): Missing info · Axel issue