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

Chicago (MDW) to Punta Cana (PUJ), Apr 27, 2027: round trips from $424, one way from $235

Chicago (MDW) to Punta Cana (PUJ), Apr 27, 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 27, 2027 – May 2, 2027; $235 one way, Axel-exclusive, Southwest Airlines, 1 stop, Apr 27, 2027; 1 adult, economy, checked Nov 13, 2026.

MDW → PUJ1 adulteconomyOne way and round trips

30 flight options · 2 airlines

Choose your return date

One-way flights and round trips by duration. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

April 2027

Flights for your trip

  1. Tue, Apr 27 · One way

    Southwest Airlines
    6:35 amMDW
    7h 15m
    MCO · 1h 50m
    2:50 pmPUJ

    Example one-way total $235 · 1 adult · Taxes included

  2. Tue, Apr 27 · One way

    Delta Air Lines
    6:00 amMDW
    8h 49m
    ATL · 3h 23m
    3:49 pmPUJ

    Example one-way total $275 · 1 adult · Taxes included

  3. Tue, Apr 27 – Wed, Apr 28

    Southwest Airlines
    6:35 amMDW
    7h 15m
    MCO · 1h 50m
    2:50 pmPUJ
    Southwest Airlines
    4:10 pmPUJ
    5h 5m
    Nonstop
    8:15 pmMDW

    Example round-trip total $450 · 1 adult · Taxes included

  4. Tue, Apr 27 – Wed, Apr 28

    Delta Air Lines
    6:00 amMDW
    8h 49m
    ATL · 3h 23m
    3:49 pmPUJ
    Delta Air Lines
    3:53 pmPUJ
    8h 24m
    ATL · 2h 29m
    11:17 pmMDW

    Example round-trip total $510 · 1 adult · Taxes included

  5. Tue, Apr 27 – Thu, Apr 29

    Southwest Airlines
    6:35 amMDW
    7h 15m
    MCO · 1h 50m
    2:50 pmPUJ
    Southwest Airlines
    4:10 pmPUJ
    5h 5m
    Nonstop
    8:15 pmMDW

    Example round-trip total $450 · 1 adult · Taxes included

  6. Tue, Apr 27 – Thu, Apr 29

    Delta Air Lines
    6:00 amMDW
    8h 49m
    ATL · 3h 23m
    3:49 pmPUJ
    Delta Air Lines
    3:53 pmPUJ
    8h 24m
    ATL · 2h 29m
    11:17 pmMDW

    Example round-trip total $510 · 1 adult · Taxes included

  7. Tue, Apr 27 – Fri, Apr 30

    Southwest Airlines
    6:35 amMDW
    7h 15m
    MCO · 1h 50m
    2:50 pmPUJ
    Southwest Airlines
    4:10 pmPUJ
    5h 5m
    Nonstop
    8:15 pmMDW

    Example round-trip total $450 · 1 adult · Taxes included

  8. Tue, Apr 27 – Fri, Apr 30

    Delta Air Lines
    6:00 amMDW
    8h 49m
    ATL · 3h 23m
    3:49 pmPUJ
    Delta Air Lines
    3:53 pmPUJ
    8h 24m
    ATL · 2h 29m
    11:17 pmMDW

    Example round-trip total $510 · 1 adult · Taxes included

  9. Tue, Apr 27 – Sat, May 1

    Southwest Airlines
    6:35 amMDW
    7h 15m
    MCO · 1h 50m
    2:50 pmPUJ
    Southwest Airlines
    4:10 pmPUJ
    5h 5m
    Nonstop
    8:15 pmMDW

    Example round-trip total $438 · 1 adult · Taxes included

  10. Tue, Apr 27 – Sat, May 1

    Delta Air Lines
    6:00 amMDW
    8h 49m
    ATL · 3h 23m
    3:49 pmPUJ
    Delta Air Lines
    3:53 pmPUJ
    8h 24m
    ATL · 2h 29m
    11:17 pmMDW

    Example round-trip total $497 · 1 adult · Taxes included

  11. Tue, Apr 27 – Mon, May 3

    Southwest Airlines
    6:35 amMDW
    7h 15m
    MCO · 1h 50m
    2:50 pmPUJ
    Southwest Airlines
    4:10 pmPUJ
    5h 5m
    Nonstop
    8:15 pmMDW

    Example round-trip total $438 · 1 adult · Taxes included

  12. Tue, Apr 27 – Mon, May 3

    Delta Air Lines
    6:00 amMDW
    8h 49m
    ATL · 3h 23m
    3:49 pmPUJ
    Delta Air Lines
    3:53 pmPUJ
    8h 24m
    ATL · 2h 29m
    11:17 pmMDW

    Example round-trip total $497 · 1 adult · Taxes included

  13. Tue, Apr 27 – Tue, May 4

    Southwest Airlines
    6:35 amMDW
    7h 15m
    MCO · 1h 50m
    2:50 pmPUJ
    Southwest Airlines
    4:10 pmPUJ
    5h 5m
    Nonstop
    8:15 pmMDW

    Example round-trip total $438 · 1 adult · Taxes included

  14. Tue, Apr 27 – Tue, May 4

    Delta Air Lines
    6:00 amMDW
    8h 49m
    ATL · 3h 23m
    3:49 pmPUJ
    Delta Air Lines
    3:53 pmPUJ
    8h 24m
    ATL · 2h 29m
    11:17 pmMDW

    Example round-trip total $497 · 1 adult · Taxes included

  15. Tue, Apr 27 – Wed, May 5

    Southwest Airlines
    6:35 amMDW
    7h 15m
    MCO · 1h 50m
    2:50 pmPUJ
    Southwest Airlines
    4:10 pmPUJ
    5h 5m
    Nonstop
    8:15 pmMDW

    Example round-trip total $438 · 1 adult · Taxes included

  16. Tue, Apr 27 – Wed, May 5

    Delta Air Lines
    6:00 amMDW
    8h 49m
    ATL · 3h 23m
    3:49 pmPUJ
    Delta Air Lines
    3:53 pmPUJ
    8h 24m
    ATL · 2h 29m
    11:17 pmMDW

    Example round-trip total $497 · 1 adult · Taxes included

  17. Tue, Apr 27 – Fri, May 7

    Southwest Airlines
    6:35 amMDW
    7h 15m
    MCO · 1h 50m
    2:50 pmPUJ
    Southwest Airlines
    4:10 pmPUJ
    5h 5m
    Nonstop
    8:15 pmMDW

    Example round-trip total $438 · 1 adult · Taxes included

  18. Tue, Apr 27 – Fri, May 7

    Delta Air Lines
    6:00 amMDW
    8h 49m
    ATL · 3h 23m
    3:49 pmPUJ
    Delta Air Lines
    3:53 pmPUJ
    8h 24m
    ATL · 2h 29m
    11:17 pmMDW

    Example round-trip total $497 · 1 adult · Taxes included

  19. Tue, Apr 27 – Sat, May 8

    Southwest Airlines
    6:35 amMDW
    7h 15m
    MCO · 1h 50m
    2:50 pmPUJ
    Southwest Airlines
    4:10 pmPUJ
    5h 5m
    Nonstop
    8:15 pmMDW

    Example round-trip total $438 · 1 adult · Taxes included

  20. Tue, Apr 27 – Sat, May 8

    Delta Air Lines
    6:00 amMDW
    8h 49m
    ATL · 3h 23m
    3:49 pmPUJ
    Delta Air Lines
    3:53 pmPUJ
    8h 24m
    ATL · 2h 29m
    11:17 pmMDW

    Example round-trip total $497 · 1 adult · Taxes included

  21. Tue, Apr 27 – Sun, May 9

    Southwest Airlines
    6:35 amMDW
    7h 15m
    MCO · 1h 50m
    2:50 pmPUJ
    Southwest Airlines
    2:45 pmPUJ
    9h 5m
    BWI · 3h 5m
    10:50 pmMDW

    Example round-trip total $424 · 1 adult · Taxes included

  22. Tue, Apr 27 – Sun, May 9

    Delta Air Lines
    6:00 amMDW
    8h 49m
    ATL · 3h 23m
    3:49 pmPUJ
    Delta Air Lines
    3:53 pmPUJ
    8h 24m
    ATL · 2h 29m
    11:17 pmMDW

    Example round-trip total $497 · 1 adult · Taxes included

  23. Tue, Apr 27 – Tue, May 11

    Southwest Airlines
    6:35 amMDW
    7h 15m
    MCO · 1h 50m
    2:50 pmPUJ
    Southwest Airlines
    4:10 pmPUJ
    5h 5m
    Nonstop
    8:15 pmMDW

    Example round-trip total $438 · 1 adult · Taxes included

  24. Tue, Apr 27 – Tue, May 11

    Delta Air Lines
    6:00 amMDW
    8h 49m
    ATL · 3h 23m
    3:49 pmPUJ
    Delta Air Lines
    3:53 pmPUJ
    8h 24m
    ATL · 2h 29m
    11:17 pmMDW

    Example round-trip total $497 · 1 adult · Taxes included

Swipe to see 23 more recent deals.

1 of 24

Make this trip yours

MDW ⇄ PUJ

Economy

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Chicago (MDW) to Punta Cana (PUJ), Apr 27, 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 27, 2027 – May 2, 2027; $235 one way, Axel-exclusive, Southwest Airlines, 1 stop, Apr 27, 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 datesAirlineFlightsTimes, duration, stopsTotal pricePrice checked
2027-04-27 · one waySouthwest AirlinesWN2964 + WN78206:35:00→14:50:00 7h 15m 1 stop via MCOAxel-exclusive $235Nov 13, 2026
2027-04-27 · one wayDelta Air LinesDL1285 + DL199006:00:00→15:49:00 8h 49m 1 stop via ATLAxel-exclusive $275Nov 13, 2026
2027-04-27 → 2027-04-28Southwest AirlinesWN2964 + WN782 / WN199906:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstopAxel-exclusive $450Nov 13, 2026
2027-04-27 → 2027-04-28Delta Air LinesDL1285 + DL1990 / DL1919 + DL107606:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATLAxel-exclusive $510Nov 13, 2026
2027-04-27 → 2027-04-29Southwest AirlinesWN2964 + WN782 / WN199906:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstopAxel-exclusive $450Nov 13, 2026
2027-04-27 → 2027-04-29Delta Air LinesDL1285 + DL1990 / DL1919 + DL107606:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATLAxel-exclusive $510Nov 13, 2026
2027-04-27 → 2027-04-30Southwest AirlinesWN2964 + WN782 / WN199906:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstopAxel-exclusive $450Nov 13, 2026
2027-04-27 → 2027-04-30Delta Air LinesDL1285 + DL1990 / DL1919 + DL107606:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATLAxel-exclusive $510Nov 13, 2026
2027-04-27 → 2027-05-01Southwest AirlinesWN2964 + WN782 / WN199906:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstopAxel-exclusive $438Nov 13, 2026
2027-04-27 → 2027-05-01Delta Air LinesDL1285 + DL1990 / DL1919 + DL107606:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATLAxel-exclusive $497Nov 13, 2026
2027-04-27 → 2027-05-02Southwest AirlinesWN2964 + WN782 / WN822 + WN25706:35:00→14:50:00 7h 15m 1 stop via MCO · 14:45:00→22:50:00 9h 05m 1 stop via BWIAxel-exclusive $424Nov 13, 2026
2027-04-27 → 2027-05-02Delta Air LinesDL1285 + DL1990 / DL1919 + DL107606:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATLAxel-exclusive $497Nov 13, 2026
2027-04-27 → 2027-05-03Southwest AirlinesWN2964 + WN782 / WN199906:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstopAxel-exclusive $438Nov 13, 2026
2027-04-27 → 2027-05-03Delta Air LinesDL1285 + DL1990 / DL1919 + DL107606:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATLAxel-exclusive $497Nov 13, 2026
2027-04-27 → 2027-05-04Southwest AirlinesWN2964 + WN782 / WN199906:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstopAxel-exclusive $438Nov 13, 2026
2027-04-27 → 2027-05-04Delta Air LinesDL1285 + DL1990 / DL1919 + DL107606:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATLAxel-exclusive $497Nov 13, 2026
2027-04-27 → 2027-05-05Southwest AirlinesWN2964 + WN782 / WN199906:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstopAxel-exclusive $438Nov 13, 2026
2027-04-27 → 2027-05-05Delta Air LinesDL1285 + DL1990 / DL1919 + DL107606:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATLAxel-exclusive $497Nov 13, 2026
2027-04-27 → 2027-05-06Southwest AirlinesWN2964 + WN782 / WN199906:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstopAxel-exclusive $438Nov 13, 2026
2027-04-27 → 2027-05-06Delta Air LinesDL1285 + DL1990 / DL1919 + DL107606:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATLAxel-exclusive $497Nov 13, 2026
2027-04-27 → 2027-05-07Southwest AirlinesWN2964 + WN782 / WN199906:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstopAxel-exclusive $438Nov 13, 2026
2027-04-27 → 2027-05-07Delta Air LinesDL1285 + DL1990 / DL1919 + DL107606:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATLAxel-exclusive $497Nov 13, 2026
2027-04-27 → 2027-05-08Southwest AirlinesWN2964 + WN782 / WN199906:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstopAxel-exclusive $438Nov 13, 2026
2027-04-27 → 2027-05-08Delta Air LinesDL1285 + DL1990 / DL1919 + DL107606:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATLAxel-exclusive $497Nov 13, 2026
2027-04-27 → 2027-05-09Southwest AirlinesWN2964 + WN782 / WN822 + WN25706:35:00→14:50:00 7h 15m 1 stop via MCO · 14:45:00→22:50:00 9h 05m 1 stop via BWIAxel-exclusive $424Nov 13, 2026
2027-04-27 → 2027-05-09Delta Air LinesDL1285 + DL1990 / DL1919 + DL107606:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATLAxel-exclusive $497Nov 13, 2026
2027-04-27 → 2027-05-10Southwest AirlinesWN2964 + WN782 / WN199906:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstopAxel-exclusive $438Nov 13, 2026
2027-04-27 → 2027-05-10Delta Air LinesDL1285 + DL1990 / DL1919 + DL107606:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATLAxel-exclusive $497Nov 13, 2026
2027-04-27 → 2027-05-11Southwest AirlinesWN2964 + WN782 / WN199906:35:00→14:50:00 7h 15m 1 stop via MCO · 16:10:00→20:15:00 5h 05m nonstopAxel-exclusive $438Nov 13, 2026
2027-04-27 → 2027-05-11Delta Air LinesDL1285 + DL1990 / DL1919 + DL107606:00:00→15:49:00 8h 49m 1 stop via ATL · 15:53:00→23:17:00 8h 24m 1 stop via ATLAxel-exclusive $497Nov 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

2027-04-27 · one way · Axel-exclusive $235

  • Southwest Airlines WN2964 / WN782: MDW 2027-04-27 06:35:00 → PUJ 2027-04-27 14:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
    • WN2964: MDW 2027-04-27 06:35:00 → MCO 2027-04-27 10:20:00; layover at MCO: 110 minutes.
    • WN782: MCO 2027-04-27 12:10:00 → PUJ 2027-04-27 14:50:00.

2027-04-27 · one way · Axel-exclusive $275

  • Delta Air Lines DL1285 / DL1990: MDW 2027-04-27 06:00:00 → PUJ 2027-04-27 15:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
    • DL1285: MDW 2027-04-27 06:00:00 → ATL 2027-04-27 09:03:00; layover at ATL: 203 minutes.
    • DL1990: ATL 2027-04-27 12:26:00 → PUJ 2027-04-27 15:49:00.

2027-04-27 → 2027-04-28 · Axel-exclusive $450

  • Southwest Airlines WN2964 / WN782: MDW 2027-04-27 06:35:00 → PUJ 2027-04-27 14:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
    • WN2964: MDW 2027-04-27 06:35:00 → MCO 2027-04-27 10:20:00; layover at MCO: 110 minutes.
    • WN782: MCO 2027-04-27 12:10:00 → PUJ 2027-04-27 14:50:00.
  • Southwest Airlines WN1999: PUJ 2027-04-28 16:10:00 → MDW 2027-04-28 20:15:00; nonstop; 305 minutes. Local airport times.

2027-04-27 → 2027-04-28 · Axel-exclusive $510

  • Delta Air Lines DL1285 / DL1990: MDW 2027-04-27 06:00:00 → PUJ 2027-04-27 15:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
    • DL1285: MDW 2027-04-27 06:00:00 → ATL 2027-04-27 09:03:00; layover at ATL: 203 minutes.
    • DL1990: ATL 2027-04-27 12:26:00 → PUJ 2027-04-27 15:49:00.
  • Delta Air Lines DL1919 / DL1076: PUJ 2027-04-28 15:53:00 → MDW 2027-04-28 23:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
    • DL1919: PUJ 2027-04-28 15:53:00 → ATL 2027-04-28 19:51:00; layover at ATL: 149 minutes.
    • DL1076: ATL 2027-04-28 22:20:00 → MDW 2027-04-28 23:17:00.

2027-04-27 → 2027-04-29 · Axel-exclusive $450

  • Southwest Airlines WN2964 / WN782: MDW 2027-04-27 06:35:00 → PUJ 2027-04-27 14:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
    • WN2964: MDW 2027-04-27 06:35:00 → MCO 2027-04-27 10:20:00; layover at MCO: 110 minutes.
    • WN782: MCO 2027-04-27 12:10:00 → PUJ 2027-04-27 14:50:00.
  • Southwest Airlines WN1999: PUJ 2027-04-29 16:10:00 → MDW 2027-04-29 20:15:00; nonstop; 305 minutes. Local airport times.

2027-04-27 → 2027-04-29 · Axel-exclusive $510

  • Delta Air Lines DL1285 / DL1990: MDW 2027-04-27 06:00:00 → PUJ 2027-04-27 15:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
    • DL1285: MDW 2027-04-27 06:00:00 → ATL 2027-04-27 09:03:00; layover at ATL: 203 minutes.
    • DL1990: ATL 2027-04-27 12:26:00 → PUJ 2027-04-27 15:49:00.
  • Delta Air Lines DL1919 / DL1076: PUJ 2027-04-29 15:53:00 → MDW 2027-04-29 23:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
    • DL1919: PUJ 2027-04-29 15:53:00 → ATL 2027-04-29 19:51:00; layover at ATL: 149 minutes.
    • DL1076: ATL 2027-04-29 22:20:00 → MDW 2027-04-29 23:17:00.

2027-04-27 → 2027-04-30 · Axel-exclusive $450

  • Southwest Airlines WN2964 / WN782: MDW 2027-04-27 06:35:00 → PUJ 2027-04-27 14:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
    • WN2964: MDW 2027-04-27 06:35:00 → MCO 2027-04-27 10:20:00; layover at MCO: 110 minutes.
    • WN782: MCO 2027-04-27 12:10:00 → PUJ 2027-04-27 14:50:00.
  • Southwest Airlines WN1999: PUJ 2027-04-30 16:10:00 → MDW 2027-04-30 20:15:00; nonstop; 305 minutes. Local airport times.

2027-04-27 → 2027-04-30 · Axel-exclusive $510

  • Delta Air Lines DL1285 / DL1990: MDW 2027-04-27 06:00:00 → PUJ 2027-04-27 15:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
    • DL1285: MDW 2027-04-27 06:00:00 → ATL 2027-04-27 09:03:00; layover at ATL: 203 minutes.
    • DL1990: ATL 2027-04-27 12:26:00 → PUJ 2027-04-27 15:49:00.
  • Delta Air Lines DL1919 / DL1076: PUJ 2027-04-30 15:53:00 → MDW 2027-04-30 23:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
    • DL1919: PUJ 2027-04-30 15:53:00 → ATL 2027-04-30 19:51:00; layover at ATL: 149 minutes.
    • DL1076: ATL 2027-04-30 22:20:00 → MDW 2027-04-30 23:17:00.

2027-04-27 → 2027-05-01 · Axel-exclusive $438

  • Southwest Airlines WN2964 / WN782: MDW 2027-04-27 06:35:00 → PUJ 2027-04-27 14:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
    • WN2964: MDW 2027-04-27 06:35:00 → MCO 2027-04-27 10:20:00; layover at MCO: 110 minutes.
    • WN782: MCO 2027-04-27 12:10:00 → PUJ 2027-04-27 14:50:00.
  • Southwest Airlines WN1999: PUJ 2027-05-01 16:10:00 → MDW 2027-05-01 20:15:00; nonstop; 305 minutes. Local airport times.

2027-04-27 → 2027-05-01 · Axel-exclusive $497

  • Delta Air Lines DL1285 / DL1990: MDW 2027-04-27 06:00:00 → PUJ 2027-04-27 15:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
    • DL1285: MDW 2027-04-27 06:00:00 → ATL 2027-04-27 09:03:00; layover at ATL: 203 minutes.
    • DL1990: ATL 2027-04-27 12:26:00 → PUJ 2027-04-27 15:49:00.
  • Delta Air Lines DL1919 / DL1076: PUJ 2027-05-01 15:53:00 → MDW 2027-05-01 23:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
    • DL1919: PUJ 2027-05-01 15:53:00 → ATL 2027-05-01 19:51:00; layover at ATL: 149 minutes.
    • DL1076: ATL 2027-05-01 22:20:00 → MDW 2027-05-01 23:17:00.

2027-04-27 → 2027-05-03 · Axel-exclusive $438

  • Southwest Airlines WN2964 / WN782: MDW 2027-04-27 06:35:00 → PUJ 2027-04-27 14:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
    • WN2964: MDW 2027-04-27 06:35:00 → MCO 2027-04-27 10:20:00; layover at MCO: 110 minutes.
    • WN782: MCO 2027-04-27 12:10:00 → PUJ 2027-04-27 14:50:00.
  • Southwest Airlines WN1999: PUJ 2027-05-03 16:10:00 → MDW 2027-05-03 20:15:00; nonstop; 305 minutes. Local airport times.

2027-04-27 → 2027-05-03 · Axel-exclusive $497

  • Delta Air Lines DL1285 / DL1990: MDW 2027-04-27 06:00:00 → PUJ 2027-04-27 15:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
    • DL1285: MDW 2027-04-27 06:00:00 → ATL 2027-04-27 09:03:00; layover at ATL: 203 minutes.
    • DL1990: ATL 2027-04-27 12:26:00 → PUJ 2027-04-27 15:49:00.
  • Delta Air Lines DL1919 / DL1076: PUJ 2027-05-03 15:53:00 → MDW 2027-05-03 23:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
    • DL1919: PUJ 2027-05-03 15:53:00 → ATL 2027-05-03 19:51:00; layover at ATL: 149 minutes.
    • DL1076: ATL 2027-05-03 22:20:00 → MDW 2027-05-03 23:17:00.

2027-04-27 → 2027-05-04 · Axel-exclusive $438

  • Southwest Airlines WN2964 / WN782: MDW 2027-04-27 06:35:00 → PUJ 2027-04-27 14:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
    • WN2964: MDW 2027-04-27 06:35:00 → MCO 2027-04-27 10:20:00; layover at MCO: 110 minutes.
    • WN782: MCO 2027-04-27 12:10:00 → PUJ 2027-04-27 14:50:00.
  • Southwest Airlines WN1999: PUJ 2027-05-04 16:10:00 → MDW 2027-05-04 20:15:00; nonstop; 305 minutes. Local airport times.

2027-04-27 → 2027-05-04 · Axel-exclusive $497

  • Delta Air Lines DL1285 / DL1990: MDW 2027-04-27 06:00:00 → PUJ 2027-04-27 15:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
    • DL1285: MDW 2027-04-27 06:00:00 → ATL 2027-04-27 09:03:00; layover at ATL: 203 minutes.
    • DL1990: ATL 2027-04-27 12:26:00 → PUJ 2027-04-27 15:49:00.
  • Delta Air Lines DL1919 / DL1076: PUJ 2027-05-04 15:53:00 → MDW 2027-05-04 23:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
    • DL1919: PUJ 2027-05-04 15:53:00 → ATL 2027-05-04 19:51:00; layover at ATL: 149 minutes.
    • DL1076: ATL 2027-05-04 22:20:00 → MDW 2027-05-04 23:17:00.

2027-04-27 → 2027-05-05 · Axel-exclusive $438

  • Southwest Airlines WN2964 / WN782: MDW 2027-04-27 06:35:00 → PUJ 2027-04-27 14:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
    • WN2964: MDW 2027-04-27 06:35:00 → MCO 2027-04-27 10:20:00; layover at MCO: 110 minutes.
    • WN782: MCO 2027-04-27 12:10:00 → PUJ 2027-04-27 14:50:00.
  • Southwest Airlines WN1999: PUJ 2027-05-05 16:10:00 → MDW 2027-05-05 20:15:00; nonstop; 305 minutes. Local airport times.

2027-04-27 → 2027-05-05 · Axel-exclusive $497

  • Delta Air Lines DL1285 / DL1990: MDW 2027-04-27 06:00:00 → PUJ 2027-04-27 15:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
    • DL1285: MDW 2027-04-27 06:00:00 → ATL 2027-04-27 09:03:00; layover at ATL: 203 minutes.
    • DL1990: ATL 2027-04-27 12:26:00 → PUJ 2027-04-27 15:49:00.
  • Delta Air Lines DL1919 / DL1076: PUJ 2027-05-05 15:53:00 → MDW 2027-05-05 23:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
    • DL1919: PUJ 2027-05-05 15:53:00 → ATL 2027-05-05 19:51:00; layover at ATL: 149 minutes.
    • DL1076: ATL 2027-05-05 22:20:00 → MDW 2027-05-05 23:17:00.

2027-04-27 → 2027-05-07 · Axel-exclusive $438

  • Southwest Airlines WN2964 / WN782: MDW 2027-04-27 06:35:00 → PUJ 2027-04-27 14:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
    • WN2964: MDW 2027-04-27 06:35:00 → MCO 2027-04-27 10:20:00; layover at MCO: 110 minutes.
    • WN782: MCO 2027-04-27 12:10:00 → PUJ 2027-04-27 14:50:00.
  • Southwest Airlines WN1999: PUJ 2027-05-07 16:10:00 → MDW 2027-05-07 20:15:00; nonstop; 305 minutes. Local airport times.

2027-04-27 → 2027-05-07 · Axel-exclusive $497

  • Delta Air Lines DL1285 / DL1990: MDW 2027-04-27 06:00:00 → PUJ 2027-04-27 15:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
    • DL1285: MDW 2027-04-27 06:00:00 → ATL 2027-04-27 09:03:00; layover at ATL: 203 minutes.
    • DL1990: ATL 2027-04-27 12:26:00 → PUJ 2027-04-27 15:49:00.
  • Delta Air Lines DL1919 / DL1076: PUJ 2027-05-07 15:53:00 → MDW 2027-05-07 23:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
    • DL1919: PUJ 2027-05-07 15:53:00 → ATL 2027-05-07 19:51:00; layover at ATL: 149 minutes.
    • DL1076: ATL 2027-05-07 22:20:00 → MDW 2027-05-07 23:17:00.

2027-04-27 → 2027-05-08 · Axel-exclusive $438

  • Southwest Airlines WN2964 / WN782: MDW 2027-04-27 06:35:00 → PUJ 2027-04-27 14:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
    • WN2964: MDW 2027-04-27 06:35:00 → MCO 2027-04-27 10:20:00; layover at MCO: 110 minutes.
    • WN782: MCO 2027-04-27 12:10:00 → PUJ 2027-04-27 14:50:00.
  • Southwest Airlines WN1999: PUJ 2027-05-08 16:10:00 → MDW 2027-05-08 20:15:00; nonstop; 305 minutes. Local airport times.

2027-04-27 → 2027-05-08 · Axel-exclusive $497

  • Delta Air Lines DL1285 / DL1990: MDW 2027-04-27 06:00:00 → PUJ 2027-04-27 15:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
    • DL1285: MDW 2027-04-27 06:00:00 → ATL 2027-04-27 09:03:00; layover at ATL: 203 minutes.
    • DL1990: ATL 2027-04-27 12:26:00 → PUJ 2027-04-27 15:49:00.
  • Delta Air Lines DL1919 / DL1076: PUJ 2027-05-08 15:53:00 → MDW 2027-05-08 23:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
    • DL1919: PUJ 2027-05-08 15:53:00 → ATL 2027-05-08 19:51:00; layover at ATL: 149 minutes.
    • DL1076: ATL 2027-05-08 22:20:00 → MDW 2027-05-08 23:17:00.

2027-04-27 → 2027-05-09 · Axel-exclusive $424

  • Southwest Airlines WN2964 / WN782: MDW 2027-04-27 06:35:00 → PUJ 2027-04-27 14:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
    • WN2964: MDW 2027-04-27 06:35:00 → MCO 2027-04-27 10:20:00; layover at MCO: 110 minutes.
    • WN782: MCO 2027-04-27 12:10:00 → PUJ 2027-04-27 14:50:00.
  • Southwest Airlines WN822 / WN257: PUJ 2027-05-09 14:45:00 → MDW 2027-05-09 22:50:00; 1 stop(s) via BWI; 545 minutes. Local airport times.
    • WN822: PUJ 2027-05-09 14:45:00 → BWI 2027-05-09 18:40:00; layover at BWI: 185 minutes.
    • WN257: BWI 2027-05-09 21:45:00 → MDW 2027-05-09 22:50:00.

2027-04-27 → 2027-05-09 · Axel-exclusive $497

  • Delta Air Lines DL1285 / DL1990: MDW 2027-04-27 06:00:00 → PUJ 2027-04-27 15:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
    • DL1285: MDW 2027-04-27 06:00:00 → ATL 2027-04-27 09:03:00; layover at ATL: 203 minutes.
    • DL1990: ATL 2027-04-27 12:26:00 → PUJ 2027-04-27 15:49:00.
  • Delta Air Lines DL1919 / DL1076: PUJ 2027-05-09 15:53:00 → MDW 2027-05-09 23:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
    • DL1919: PUJ 2027-05-09 15:53:00 → ATL 2027-05-09 19:51:00; layover at ATL: 149 minutes.
    • DL1076: ATL 2027-05-09 22:20:00 → MDW 2027-05-09 23:17:00.

2027-04-27 → 2027-05-11 · Axel-exclusive $438

  • Southwest Airlines WN2964 / WN782: MDW 2027-04-27 06:35:00 → PUJ 2027-04-27 14:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
    • WN2964: MDW 2027-04-27 06:35:00 → MCO 2027-04-27 10:20:00; layover at MCO: 110 minutes.
    • WN782: MCO 2027-04-27 12:10:00 → PUJ 2027-04-27 14:50:00.
  • Southwest Airlines WN1999: PUJ 2027-05-11 16:10:00 → MDW 2027-05-11 20:15:00; nonstop; 305 minutes. Local airport times.

2027-04-27 → 2027-05-11 · Axel-exclusive $497

  • Delta Air Lines DL1285 / DL1990: MDW 2027-04-27 06:00:00 → PUJ 2027-04-27 15:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
    • DL1285: MDW 2027-04-27 06:00:00 → ATL 2027-04-27 09:03:00; layover at ATL: 203 minutes.
    • DL1990: ATL 2027-04-27 12:26:00 → PUJ 2027-04-27 15:49:00.
  • Delta Air Lines DL1919 / DL1076: PUJ 2027-05-11 15:53:00 → MDW 2027-05-11 23:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
    • DL1919: PUJ 2027-05-11 15:53:00 → ATL 2027-05-11 19:51:00; layover at ATL: 149 minutes.
    • DL1076: ATL 2027-05-11 22:20:00 → MDW 2027-05-11 23:17:00.

Explore this route

For AI assistants

  • This page: Chicago (MDW) to Punta Cana (PUJ) · Apr 27, 2027 · 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.