American Airlines flights from Chicago to Punta Cana

Recent searches for flights from Chicago to Punta Cana

Aug 2026
From$380*
Updated: 4 hours ago
Round tripIEconomy
Sep 2026
From$380*
Updated: 3 hours ago
Round tripIEconomy
Oct 2026
From$375*
Updated: 4 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $380
cmp-daily-histogram-bars-legend-max-price-aria-label $2.7K
Displaying fares for August-2026
  • CHI–PUJ, 08/05/26 – 08/12/26: From $901
    05

    We

    AUG

  • ORD–PUJ, 08/06/26 – 08/13/26: From $830
    06

    Th

  • ORD–PUJ, 08/07/26 – 08/14/26: From $662
    07

    Fr

  • CHI–PUJ, 08/08/26 – 08/15/26: From $702
    08

    Sa

  • ORD–PUJ, 08/09/26 – 08/16/26: From $824
    09

    Su

  • ORD–PUJ, 08/10/26 – 08/17/26: From $698
    10

    Mo

  • ORD–PUJ, 08/11/26 – 08/18/26: From $655
    11

    Tu

  • CHI–PUJ, 08/12/26 – 08/19/26: From $627
    12

    We

  • ORD–PUJ, 08/13/26 – 08/20/26: From $622
    13

    Th

  • ORD–PUJ, 08/14/26 – 08/21/26: From $632
    14

    Fr

  • CHI–PUJ, 08/15/26 – 08/22/26: From $668
    15

    Sa

  • ORD–PUJ, 08/16/26 – 08/23/26: From $763
    16

    Su

  • CHI–PUJ, 08/17/26 – 08/24/26: From $662
    17

    Mo

  • ORD–PUJ, 08/18/26 – 08/25/26: From $650
    18

    Tu

  • ORD–PUJ, 08/19/26 – 08/26/26: From $528
    19

    We

  • ORD–PUJ, 08/20/26 – 08/27/26: From $430
    20

    Th

  • ORD–PUJ, 08/21/26 – 08/28/26: From $470
    21

    Fr

  • ORD–PUJ, 08/22/26 – 08/27/26: From $430
    22

    Sa

  • CHI–PUJ, 08/23/26 – 08/30/26: From $700
    23

    Su

  • ORD–PUJ, 08/24/26 – 08/31/26: From $690
    24

    Mo

  • ORD–PUJ, 08/25/26 – 09/01/26: From $547
    25

    Tu

  • CHI–PUJ, 08/26/26 – 09/02/26: From $395
    26

    We

  • ORD–PUJ, 08/27/26 – 09/03/26: From $380
    27

    Th

  • CHI–PUJ, 08/28/26 – 09/04/26: From $380
    28

    Fr

  • CHI–PUJ, 08/29/26 – 09/05/26: From $390
    29

    Sa

  • ORD–PUJ, 08/30/26 – 09/06/26: From $750
    30

    Su

  • ORD–PUJ, 08/31/26 – 09/07/26: From $2,711
    31

    Mo

  • ORD–PUJ, 09/01/26 – 09/08/26: From $674
    01

    Tu

    SEP

  • ORD–PUJ, 09/02/26 – 09/09/26: From $683
    02

    We

  • ORD–PUJ, 09/03/26 – 09/10/26: From $430
    03

    Th

  • ORD–PUJ, 09/04/26 – 09/11/26: From $551
    04

    Fr

    • range$380-$2,711

    DisclaimerFares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Fares listed may be Basic Economy, which class is subject to additional terms and conditions. Additional baggage fees and charges for optional products and services may apply.

    Find deals on Chicago to Punta Cana flights

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    Chicago (ORD)to

    Punta Cana (PUJ)
    10/26/26 - 11/02/26

    Round trip

    Economy

    from
    $375Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    Punta Cana (PUJ)
    09/29/26 - 10/06/26

    Round trip

    Economy

    from
    $380Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    Punta Cana (PUJ)
    10/22/26 - 10/29/26

    Round trip

    Economy

    from
    $380Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    Punta Cana (PUJ)
    10/29/26 - 11/05/26

    Round trip

    Economy

    from
    $380Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    Punta Cana (PUJ)
    11/27/26 - 12/04/26

    Round trip

    Economy

    from
    $380Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    Punta Cana (PUJ)
    08/27/26 - 09/03/26

    Round trip

    Economy

    from
    $380Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    Punta Cana (PUJ)
    10/15/26 - 10/22/26

    Round trip

    Economy

    from
    $380Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    Punta Cana (PUJ)
    08/28/26 - 09/04/26

    Round trip

    Economy

    from
    $380Fare subject to changes
    Updated: 4 hours ago

    *Fares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Some fares listed may include one or more connections that are Basic Economy, which class is subject to additional terms and conditions. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Additional baggage fees and charges for optional products and services may apply.

    Finding cheap flights from Chicago to Punta Cana

    Looking for lower fares on your trip from Chicago to Punta Cana? Here are a few ways to save.

    • Book early: Booking 1 to 3 months ahead can help you find lower fares
    • Be flexible with dates: Midweek travel, like Tuesdays and Wednesdays, can be more affordable
    • Travel during less busy periods: Flying outside peak travel times can help find lower fares and avoid crowds

    Earn up to $500 back on your next American Airlines flight plus, 30,000 bonus miles. Offers vary elsewhere. Opens another site in a new window that may not meet accessibility guidelines.

    Upgrade your flight with Main Cabin Extra

    Make your trip more comfortable with Main Cabin Extra. Enjoy benefits like:

    • Extra legroom: More space with seats at the front of the Main Cabin or in exit rows.
    • Early boarding: Preferred Group 5 boarding allows easier access to overhead bins.
    • Complimentary drinks: Enjoy beer, wine and spirits on flights with full beverage service.

    Discover how Main Cabin Extra can enhance your trip.

    American Airlines flights from Chicago to Punta Cana