Chicago (MDW) to Punta Cana (PUJ), Mar 26, 2027: round trips from $537, one way from $328

Chicago (MDW) to Punta Cana (PUJ), Mar 26, 2027: round trips from $537, one way from $328 on Axel, checked Nov 13, 2026. Lowest published fares: $537 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Mar 26, 2027 – Apr 5, 2027; $328 one way, Axel-exclusive, Southwest Airlines, 1 stop, Mar 26, 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
2027-03-26 · one way Southwest Airlines WN2964 + WN782 06:35:00→14:50:00 7h 15m 1 stop via MCO Axel-exclusive $328 Nov 13, 2026
2027-03-26 · one way Delta Air Lines DL1285 + DL1990 06:00:00→15:49:00 8h 49m 1 stop via ATL Axel-exclusive $386 Nov 13, 2026
2027-03-26 → 2027-03-27 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 $632 Nov 13, 2026
2027-03-26 → 2027-03-27 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 $721 Nov 13, 2026
2027-03-26 → 2027-03-28 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 $590 Nov 13, 2026
2027-03-26 → 2027-03-28 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 $694 Nov 13, 2026
2027-03-26 → 2027-03-29 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 $609 Nov 13, 2026
2027-03-26 → 2027-03-29 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 $694 Nov 13, 2026
2027-03-26 → 2027-03-30 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 $609 Nov 13, 2026
2027-03-26 → 2027-03-30 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 $694 Nov 13, 2026
2027-03-26 → 2027-03-31 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 $609 Nov 13, 2026
2027-03-26 → 2027-03-31 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 $694 Nov 13, 2026
2027-03-26 → 2027-04-01 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 $595 Nov 13, 2026
2027-03-26 → 2027-04-01 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 $679 Nov 13, 2026
2027-03-26 → 2027-04-02 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 $595 Nov 13, 2026
2027-03-26 → 2027-04-02 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 $679 Nov 13, 2026
2027-03-26 → 2027-04-03 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 $595 Nov 13, 2026
2027-03-26 → 2027-04-03 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 $679 Nov 13, 2026
2027-03-26 → 2027-04-04 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 $576 Nov 13, 2026
2027-03-26 → 2027-04-04 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 $679 Nov 13, 2026
2027-03-26 → 2027-04-05 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 $537 Nov 13, 2026
2027-03-26 → 2027-04-05 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 $615 Nov 13, 2026
2027-03-26 → 2027-04-06 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 $537 Nov 13, 2026
2027-03-26 → 2027-04-06 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 $615 Nov 13, 2026
2027-03-26 → 2027-04-07 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 $537 Nov 13, 2026
2027-03-26 → 2027-04-07 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 $615 Nov 13, 2026
2027-03-26 → 2027-04-08 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 $537 Nov 13, 2026
2027-03-26 → 2027-04-08 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 $615 Nov 13, 2026
2027-03-26 → 2027-04-09 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 $537 Nov 13, 2026
2027-03-26 → 2027-04-09 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 $615 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

2027-03-26 · one way · Axel-exclusive $328

2027-03-26 · one way · Axel-exclusive $386

2027-03-26 → 2027-03-27 · Axel-exclusive $632

2027-03-26 → 2027-03-27 · Axel-exclusive $721

2027-03-26 → 2027-03-28 · Axel-exclusive $590

2027-03-26 → 2027-03-28 · Axel-exclusive $694

2027-03-26 → 2027-03-29 · Axel-exclusive $609

2027-03-26 → 2027-03-29 · Axel-exclusive $694

2027-03-26 → 2027-03-30 · Axel-exclusive $609

2027-03-26 → 2027-03-30 · Axel-exclusive $694

2027-03-26 → 2027-04-01 · Axel-exclusive $595

2027-03-26 → 2027-04-01 · Axel-exclusive $679

2027-03-26 → 2027-04-02 · Axel-exclusive $595

2027-03-26 → 2027-04-02 · Axel-exclusive $679

2027-03-26 → 2027-04-03 · Axel-exclusive $595

2027-03-26 → 2027-04-03 · Axel-exclusive $679

2027-03-26 → 2027-04-05 · Axel-exclusive $537

2027-03-26 → 2027-04-05 · Axel-exclusive $615

2027-03-26 → 2027-04-06 · Axel-exclusive $537

2027-03-26 → 2027-04-06 · Axel-exclusive $615

2027-03-26 → 2027-04-07 · Axel-exclusive $537

2027-03-26 → 2027-04-07 · Axel-exclusive $615

2027-03-26 → 2027-04-09 · Axel-exclusive $537

2027-03-26 → 2027-04-09 · Axel-exclusive $615

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