Chicago (MDW) to Punta Cana (PUJ), Mar 29, 2027: round trips from $502, one way from $308

Chicago (MDW) to Punta Cana (PUJ), Mar 29, 2027: round trips from $502, one way from $308 on Axel, checked Nov 13, 2026. Lowest published fares: $502 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Mar 29, 2027 – Apr 11, 2027; $308 one way, Axel-exclusive, Southwest Airlines, 1 stop, Mar 29, 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
2027-03-29 · one way Southwest Airlines WN2964 + WN782 06:35:00→14:50:00 7h 15m 1 stop via MCO Axel-exclusive $308 Nov 13, 2026
2027-03-29 · one way Delta Air Lines DL1285 + DL1990 06:00:00→15:49:00 8h 49m 1 stop via ATL Axel-exclusive $360 Nov 13, 2026
2027-03-29 → 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 $590 Nov 13, 2026
2027-03-29 → 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 $668 Nov 13, 2026
2027-03-29 → 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 $590 Nov 13, 2026
2027-03-29 → 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 $668 Nov 13, 2026
2027-03-29 → 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 $576 Nov 13, 2026
2027-03-29 → 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 $653 Nov 13, 2026
2027-03-29 → 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 $576 Nov 13, 2026
2027-03-29 → 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 $653 Nov 13, 2026
2027-03-29 → 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 $576 Nov 13, 2026
2027-03-29 → 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 $653 Nov 13, 2026
2027-03-29 → 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 $557 Nov 13, 2026
2027-03-29 → 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 $653 Nov 13, 2026
2027-03-29 → 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 $517 Nov 13, 2026
2027-03-29 → 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 $589 Nov 13, 2026
2027-03-29 → 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 $517 Nov 13, 2026
2027-03-29 → 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 $589 Nov 13, 2026
2027-03-29 → 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 $517 Nov 13, 2026
2027-03-29 → 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 $589 Nov 13, 2026
2027-03-29 → 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 $517 Nov 13, 2026
2027-03-29 → 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 $589 Nov 13, 2026
2027-03-29 → 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 $517 Nov 13, 2026
2027-03-29 → 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 $589 Nov 13, 2026
2027-03-29 → 2027-04-10 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 $517 Nov 13, 2026
2027-03-29 → 2027-04-10 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 $589 Nov 13, 2026
2027-03-29 → 2027-04-11 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 $502 Nov 13, 2026
2027-03-29 → 2027-04-11 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 $589 Nov 13, 2026
2027-03-29 → 2027-04-12 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 $517 Nov 13, 2026
2027-03-29 → 2027-04-12 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 $589 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

2027-03-29 · one way · Axel-exclusive $308

2027-03-29 · one way · Axel-exclusive $360

2027-03-29 → 2027-03-30 · Axel-exclusive $590

2027-03-29 → 2027-03-30 · Axel-exclusive $668

2027-03-29 → 2027-03-31 · Axel-exclusive $590

2027-03-29 → 2027-03-31 · Axel-exclusive $668

2027-03-29 → 2027-04-01 · Axel-exclusive $576

2027-03-29 → 2027-04-01 · Axel-exclusive $653

2027-03-29 → 2027-04-02 · Axel-exclusive $576

2027-03-29 → 2027-04-02 · Axel-exclusive $653

2027-03-29 → 2027-04-04 · Axel-exclusive $557

2027-03-29 → 2027-04-04 · Axel-exclusive $653

2027-03-29 → 2027-04-05 · Axel-exclusive $517

2027-03-29 → 2027-04-05 · Axel-exclusive $589

2027-03-29 → 2027-04-06 · Axel-exclusive $517

2027-03-29 → 2027-04-06 · Axel-exclusive $589

2027-03-29 → 2027-04-08 · Axel-exclusive $517

2027-03-29 → 2027-04-08 · Axel-exclusive $589

2027-03-29 → 2027-04-09 · Axel-exclusive $517

2027-03-29 → 2027-04-09 · Axel-exclusive $589

2027-03-29 → 2027-04-10 · Axel-exclusive $517

2027-03-29 → 2027-04-10 · Axel-exclusive $589

2027-03-29 → 2027-04-12 · Axel-exclusive $517

2027-03-29 → 2027-04-12 · Axel-exclusive $589

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