American Airlines flights from Chicago to Punta Cana

Recent searches for flights from Chicago to Punta Cana

Aug 2026
From$505*
Updated: 7 hours ago
Round tripIEconomy
Sep 2026
From$410*
Updated: 7 hours ago
Round tripIEconomy
Oct 2026
From$400*
Updated: 8 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $480
cmp-daily-histogram-bars-legend-max-price-aria-label $1.3K
Displaying fares for August-2026
  • ORD–PUJ, 08/24/26 – 08/26/26: From $734
    24

    Mo

    AUG

  • ORD–PUJ, 08/25/26 – 09/01/26: From $855
    25

    Tu

  • CHI–PUJ, 08/26/26 – 09/02/26: From $647
    26

    We

  • ORD–PUJ, 08/27/26 – 09/03/26: From $520
    27

    Th

  • CHI–PUJ, 08/28/26 – 09/04/26: From $505
    28

    Fr

  • CHI–PUJ, 08/29/26 – 09/05/26: From $516
    29

    Sa

  • ORD–PUJ, 08/30/26 – 09/06/26: From $746
    30

    Su

  • ORD–PUJ, 08/31/26 – 09/07/26: From $1,251
    31

    Mo

  • ORD–PUJ, 09/01/26 – 09/04/26: From $480
    01

    Tu

    SEP

  • CHI–PUJ, 09/02/26 – 09/09/26: From $708
    02

    We

  • CHI–PUJ, 09/03/26 – 09/10/26: From $490
    03

    Th

  • ORD–PUJ, 09/04/26 – 09/11/26: From $595
    04

    Fr

  • CHI–PUJ, 09/05/26 – 09/12/26: From $715
    05

    Sa

  • ORD–PUJ, 09/06/26 – 09/12/26: From $742
    06

    Su

  • ORD–PUJ, 09/07/26 – 09/12/26: From $738
    07

    Mo

  • ORD–PUJ, 09/08/26 – 09/15/26: From $1,183
    08

    Tu

  • ORD–PUJ, 09/09/26 – 09/18/26: From $605
    09

    We

  • ORD–PUJ, 09/10/26 – 09/17/26: From $555
    10

    Th

  • CHI–PUJ, 09/11/26 – 09/18/26: From $495
    11

    Fr

  • ORD–PUJ, 09/12/26 – 09/19/26: From $715
    12

    Sa

  • CHI–PUJ, 09/13/26 – 09/20/26: From $835
    13

    Su

  • ORD–PUJ, 09/14/26 – 09/21/26: From $711
    14

    Mo

  • ORD–PUJ, 09/15/26 – 09/22/26: From $781
    15

    Tu

  • ORD–PUJ, 09/16/26 – 09/23/26: From $673
    16

    We

  • CHI–PUJ, 09/17/26 – 09/24/26: From $675
    17

    Th

  • CHI–PUJ, 09/18/26 – 09/25/26: From $503
    18

    Fr

  • ORD–PUJ, 09/19/26 – 09/26/26: From $510
    19

    Sa

  • CHI–PUJ, 09/20/26 – 09/27/26: From $764
    20

    Su

  • CHI–PUJ, 09/21/26 – 09/28/26: From $671
    21

    Mo

  • CHI–PUJ, 09/22/26 – 09/29/26: From $712
    22

    Tu

  • CHI–PUJ, 09/23/26 – 09/30/26: From $875
    23

    We

    • range$480-$1,251

    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)
    11/08/26 - 11/12/26

    Round trip

    Economy

    from
    $400Fare subject to changes
    Updated: 21 hours ago

    Chicago (ORD)to

    Punta Cana (PUJ)
    02/09/27 - 02/18/27

    Round trip

    Economy

    from
    $395Fare subject to changes
    Updated: 33 minutes ago

    Chicago (ORD)to

    Punta Cana (PUJ)
    01/10/27 - 01/14/27

    Round trip

    Economy

    from
    $395Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    Punta Cana (PUJ)
    01/11/27 - 01/14/27

    Round trip

    Economy

    from
    $395Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    Punta Cana (PUJ)
    11/14/26 - 11/21/26

    Round trip

    Economy

    from
    $400Fare subject to changes
    Updated: 8 hours ago

    Chicago (ORD)to

    Punta Cana (PUJ)
    12/03/26 - 12/10/26

    Round trip

    Economy

    from
    $400Fare subject to changes
    Updated: 8 hours ago

    Chicago (ORD)to

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

    Round trip

    Economy

    from
    $400Fare subject to changes
    Updated: 8 hours ago

    Chicago (ORD)to

    Punta Cana (PUJ)
    11/11/26 - 11/18/26

    Round trip

    Economy

    from
    $405Fare subject to changes
    Updated: 8 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