Chicago (MDW) to Punta Cana (PUJ), Apr 20, 2027: round trips from $424, one way from $235

Chicago (MDW) to Punta Cana (PUJ), Apr 20, 2027: round trips from $424, one way from $235 on Axel, checked Nov 13, 2026. Lowest published fares: $424 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Apr 20, 2027 – May 2, 2027; $235 one way, Axel-exclusive, Southwest Airlines, 1 stop, Apr 20, 2027; 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.

Exact travel dates Airline Flights Times, duration, stops Total price Price checked
2027-04-20 · one way Southwest Airlines WN2964 + WN782 06:35:00→14:50:00 7h 15m 1 stop via MCO Axel-exclusive $235 Nov 13, 2026
2027-04-20 · one way Delta Air Lines DL1285 + DL1990 06:00:00→15:49:00 8h 49m 1 stop via ATL Axel-exclusive $275 Nov 13, 2026
2027-04-20 → 2027-04-21 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstop Axel-exclusive $450 Nov 13, 2026
2027-04-20 → 2027-04-21 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATL Axel-exclusive $510 Nov 13, 2026
2027-04-20 → 2027-04-22 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstop Axel-exclusive $450 Nov 13, 2026
2027-04-20 → 2027-04-22 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATL Axel-exclusive $510 Nov 13, 2026
2027-04-20 → 2027-04-23 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstop Axel-exclusive $450 Nov 13, 2026
2027-04-20 → 2027-04-23 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATL Axel-exclusive $510 Nov 13, 2026
2027-04-20 → 2027-04-24 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstop Axel-exclusive $450 Nov 13, 2026
2027-04-20 → 2027-04-24 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATL Axel-exclusive $510 Nov 13, 2026
2027-04-20 → 2027-04-25 Southwest Airlines WN2964 + WN782 / WN822 + WN257 06:35:00→14:50:00 7h 15m 1 stop via MCO · 14:45:00→22:50:00 9h 05m 1 stop via BWI Axel-exclusive $435 Nov 13, 2026
2027-04-20 → 2027-04-25 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATL Axel-exclusive $510 Nov 13, 2026
2027-04-20 → 2027-04-26 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstop Axel-exclusive $450 Nov 13, 2026
2027-04-20 → 2027-04-26 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATL Axel-exclusive $510 Nov 13, 2026
2027-04-20 → 2027-04-27 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstop Axel-exclusive $450 Nov 13, 2026
2027-04-20 → 2027-04-27 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATL Axel-exclusive $510 Nov 13, 2026
2027-04-20 → 2027-04-28 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstop Axel-exclusive $450 Nov 13, 2026
2027-04-20 → 2027-04-28 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATL Axel-exclusive $510 Nov 13, 2026
2027-04-20 → 2027-04-29 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstop Axel-exclusive $450 Nov 13, 2026
2027-04-20 → 2027-04-29 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATL Axel-exclusive $510 Nov 13, 2026
2027-04-20 → 2027-04-30 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstop Axel-exclusive $450 Nov 13, 2026
2027-04-20 → 2027-04-30 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATL Axel-exclusive $510 Nov 13, 2026
2027-04-20 → 2027-05-01 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstop Axel-exclusive $438 Nov 13, 2026
2027-04-20 → 2027-05-01 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATL Axel-exclusive $497 Nov 13, 2026
2027-04-20 → 2027-05-02 Southwest Airlines WN2964 + WN782 / WN822 + WN257 06:35:00→14:50:00 7h 15m 1 stop via MCO · 14:45:00→22:50:00 9h 05m 1 stop via BWI Axel-exclusive $424 Nov 13, 2026
2027-04-20 → 2027-05-02 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATL Axel-exclusive $497 Nov 13, 2026
2027-04-20 → 2027-05-03 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstop Axel-exclusive $438 Nov 13, 2026
2027-04-20 → 2027-05-03 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATL Axel-exclusive $497 Nov 13, 2026
2027-04-20 → 2027-05-04 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstop Axel-exclusive $438 Nov 13, 2026
2027-04-20 → 2027-05-04 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATL Axel-exclusive $497 Nov 13, 2026

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.

All hotels in Punta Cana

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

2027-04-20 · one way · Axel-exclusive $235

2027-04-20 · one way · Axel-exclusive $275

2027-04-20 → 2027-04-21 · Axel-exclusive $450

2027-04-20 → 2027-04-21 · Axel-exclusive $510

2027-04-20 → 2027-04-22 · Axel-exclusive $450

2027-04-20 → 2027-04-22 · Axel-exclusive $510

2027-04-20 → 2027-04-23 · Axel-exclusive $450

2027-04-20 → 2027-04-23 · Axel-exclusive $510

2027-04-20 → 2027-04-24 · Axel-exclusive $450

2027-04-20 → 2027-04-24 · Axel-exclusive $510

2027-04-20 → 2027-04-26 · Axel-exclusive $450

2027-04-20 → 2027-04-26 · Axel-exclusive $510

2027-04-20 → 2027-04-27 · Axel-exclusive $450

2027-04-20 → 2027-04-27 · Axel-exclusive $510

2027-04-20 → 2027-04-28 · Axel-exclusive $450

2027-04-20 → 2027-04-28 · Axel-exclusive $510

2027-04-20 → 2027-04-30 · Axel-exclusive $450

2027-04-20 → 2027-04-30 · Axel-exclusive $510

2027-04-20 → 2027-05-01 · Axel-exclusive $438

2027-04-20 → 2027-05-01 · Axel-exclusive $497

2027-04-20 → 2027-05-02 · Axel-exclusive $424

2027-04-20 → 2027-05-02 · Axel-exclusive $497

2027-04-20 → 2027-05-04 · Axel-exclusive $438

2027-04-20 → 2027-05-04 · Axel-exclusive $497

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