Chicago (MDW) to Punta Cana (PUJ), Dec 30, 2026: round trips from $558, one way from $350

Chicago (MDW) to Punta Cana (PUJ), Dec 30, 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 30, 2026 – Jan 10, 2027; $350 one way, Axel-exclusive, Southwest Airlines, 1 stop, Dec 30, 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.

Exact travel dates Airline Flights Times, duration, stops Total price Price checked
2026-12-30 · one way Southwest Airlines WN2964 + WN782 06:35:00→15:50:00 7h 15m 1 stop via MCO Axel-exclusive $350 Nov 13, 2026
2026-12-30 · one way Delta Air Lines DL1285 + DL1990 06:00:00→16:49:00 8h 49m 1 stop via ATL Axel-exclusive $413 Nov 13, 2026
2026-12-30 → 2026-12-31 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→15:50:00 7h 15m 1 stop via MCO · 16:10:00→19:15:00 5h 05m nonstop Axel-exclusive $676 Nov 13, 2026
2026-12-30 → 2026-12-31 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→16:49:00 8h 49m 1 stop via ATL · 15:53:00→22:17:00 8h 24m 1 stop via ATL Axel-exclusive $770 Nov 13, 2026
2026-12-30 → 2027-01-01 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→15:50:00 7h 15m 1 stop via MCO · 16:10:00→19:15:00 5h 05m nonstop Axel-exclusive $676 Nov 13, 2026
2026-12-30 → 2027-01-01 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→16:49:00 8h 49m 1 stop via ATL · 15:53:00→22:17:00 8h 24m 1 stop via ATL Axel-exclusive $770 Nov 13, 2026
2026-12-30 → 2027-01-02 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→15:50:00 7h 15m 1 stop via MCO · 16:10:00→19:15:00 5h 05m nonstop Axel-exclusive $676 Nov 13, 2026
2026-12-30 → 2027-01-02 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→16:49:00 8h 49m 1 stop via ATL · 15:53:00→22:17:00 8h 24m 1 stop via ATL Axel-exclusive $770 Nov 13, 2026
2026-12-30 → 2027-01-03 Southwest Airlines WN2964 + WN782 / WN822 + WN257 06:35:00→15:50:00 7h 15m 1 stop via MCO · 14:45:00→21:50:00 9h 05m 1 stop via BWI Axel-exclusive $651 Nov 13, 2026
2026-12-30 → 2027-01-03 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→16:49:00 8h 49m 1 stop via ATL · 15:53:00→22:17:00 8h 24m 1 stop via ATL Axel-exclusive $770 Nov 13, 2026
2026-12-30 → 2027-01-04 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→15:50:00 7h 15m 1 stop via MCO · 16:10:00→19:15:00 5h 05m nonstop Axel-exclusive $576 Nov 13, 2026
2026-12-30 → 2027-01-04 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→16:49:00 8h 49m 1 stop via ATL · 15:53:00→22:17:00 8h 24m 1 stop via ATL Axel-exclusive $660 Nov 13, 2026
2026-12-30 → 2027-01-05 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→15:50:00 7h 15m 1 stop via MCO · 16:10:00→19:15:00 5h 05m nonstop Axel-exclusive $576 Nov 13, 2026
2026-12-30 → 2027-01-05 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→16:49:00 8h 49m 1 stop via ATL · 15:53:00→22:17:00 8h 24m 1 stop via ATL Axel-exclusive $660 Nov 13, 2026
2026-12-30 → 2027-01-06 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→15:50:00 7h 15m 1 stop via MCO · 16:10:00→19:15:00 5h 05m nonstop Axel-exclusive $576 Nov 13, 2026
2026-12-30 → 2027-01-06 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→16:49:00 8h 49m 1 stop via ATL · 15:53:00→22:17:00 8h 24m 1 stop via ATL Axel-exclusive $660 Nov 13, 2026
2026-12-30 → 2027-01-07 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→15:50:00 7h 15m 1 stop via MCO · 16:10:00→19:15:00 5h 05m nonstop Axel-exclusive $576 Nov 13, 2026
2026-12-30 → 2027-01-07 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→16:49:00 8h 49m 1 stop via ATL · 15:53:00→22:17:00 8h 24m 1 stop via ATL Axel-exclusive $660 Nov 13, 2026
2026-12-30 → 2027-01-08 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→15:50:00 7h 15m 1 stop via MCO · 16:10:00→19:15:00 5h 05m nonstop Axel-exclusive $576 Nov 13, 2026
2026-12-30 → 2027-01-08 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→16:49:00 8h 49m 1 stop via ATL · 15:53:00→22:17:00 8h 24m 1 stop via ATL Axel-exclusive $660 Nov 13, 2026
2026-12-30 → 2027-01-09 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→15:50:00 7h 15m 1 stop via MCO · 16:10:00→19:15:00 5h 05m nonstop Axel-exclusive $576 Nov 13, 2026
2026-12-30 → 2027-01-09 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→16:49:00 8h 49m 1 stop via ATL · 15:53:00→22:17:00 8h 24m 1 stop via ATL Axel-exclusive $660 Nov 13, 2026
2026-12-30 → 2027-01-10 Southwest Airlines WN2964 + WN782 / WN822 + WN257 06:35:00→15:50:00 7h 15m 1 stop via MCO · 14:45:00→21:50:00 9h 05m 1 stop via BWI Axel-exclusive $558 Nov 13, 2026
2026-12-30 → 2027-01-10 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→16:49:00 8h 49m 1 stop via ATL · 15:53:00→22:17:00 8h 24m 1 stop via ATL Axel-exclusive $660 Nov 13, 2026
2026-12-30 → 2027-01-11 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→15:50:00 7h 15m 1 stop via MCO · 16:10:00→19:15:00 5h 05m nonstop Axel-exclusive $576 Nov 13, 2026
2026-12-30 → 2027-01-11 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→16:49:00 8h 49m 1 stop via ATL · 15:53:00→22:17:00 8h 24m 1 stop via ATL Axel-exclusive $660 Nov 13, 2026
2026-12-30 → 2027-01-12 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→15:50:00 7h 15m 1 stop via MCO · 16:10:00→19:15:00 5h 05m nonstop Axel-exclusive $576 Nov 13, 2026
2026-12-30 → 2027-01-12 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→16:49:00 8h 49m 1 stop via ATL · 15:53:00→22:17:00 8h 24m 1 stop via ATL Axel-exclusive $660 Nov 13, 2026
2026-12-30 → 2027-01-13 Southwest Airlines WN2964 + WN782 / WN1999 06:35:00→15:50:00 7h 15m 1 stop via MCO · 16:10:00→19:15:00 5h 05m nonstop Axel-exclusive $576 Nov 13, 2026
2026-12-30 → 2027-01-13 Delta Air Lines DL1285 + DL1990 / DL1919 + DL1076 06:00:00→16:49:00 8h 49m 1 stop via ATL · 15:53:00→22:17:00 8h 24m 1 stop via ATL Axel-exclusive $660 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

2026-12-30 · one way · Axel-exclusive $350

2026-12-30 · one way · Axel-exclusive $413

2026-12-30 → 2026-12-31 · Axel-exclusive $676

2026-12-30 → 2026-12-31 · Axel-exclusive $770

2026-12-30 → 2027-01-01 · Axel-exclusive $676

2026-12-30 → 2027-01-01 · Axel-exclusive $770

2026-12-30 → 2027-01-02 · Axel-exclusive $676

2026-12-30 → 2027-01-02 · Axel-exclusive $770

2026-12-30 → 2027-01-03 · Axel-exclusive $651

2026-12-30 → 2027-01-03 · Axel-exclusive $770

2026-12-30 → 2027-01-05 · Axel-exclusive $576

2026-12-30 → 2027-01-05 · Axel-exclusive $660

2026-12-30 → 2027-01-06 · Axel-exclusive $576

2026-12-30 → 2027-01-06 · Axel-exclusive $660

2026-12-30 → 2027-01-07 · Axel-exclusive $576

2026-12-30 → 2027-01-07 · Axel-exclusive $660

2026-12-30 → 2027-01-09 · Axel-exclusive $576

2026-12-30 → 2027-01-09 · Axel-exclusive $660

2026-12-30 → 2027-01-10 · Axel-exclusive $558

2026-12-30 → 2027-01-10 · Axel-exclusive $660

2026-12-30 → 2027-01-11 · Axel-exclusive $576

2026-12-30 → 2027-01-11 · Axel-exclusive $660

2026-12-30 → 2027-01-13 · Axel-exclusive $576

2026-12-30 → 2027-01-13 · Axel-exclusive $660

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