American Airlines flights from Chicago to Puerto Plata

Recent searches for flights from Chicago to Puerto Plata

Aug 2026
From$745*
Updated: 11 hours ago
Round tripIEconomy
Sep 2026
From$630*
Updated: 11 hours ago
Round tripIEconomy
Oct 2026
From$630*
Updated: 11 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $664
cmp-daily-histogram-bars-legend-max-price-aria-label $1.8K
Displaying fares for August-2026
  • ORD–POP, 08/14/26 – 08/21/26: From $1,040
    14

    Fr

    AUG

  • CHI–POP, 08/15/26 – 08/22/26: From $1,040
    15

    Sa

  • CHI–POP, 08/16/26 – 08/23/26: From $1,775
    16

    Su

  • ORD–POP, 08/17/26 – 08/24/26: From $1,770
    17

    Mo

  • CHI–POP, 08/18/26 – 08/25/26: From $1,028
    18

    Tu

  • CHI–POP, 08/19/26 – 08/26/26: From $1,033
    19

    We

  • CHI–POP, 08/20/26 – 08/27/26: From $886
    20

    Th

  • CHI–POP, 08/21/26 – 08/28/26: From $886
    21

    Fr

  • CHI–POP, 08/22/26 – 08/29/26: From $920
    22

    Sa

  • CHI–POP, 08/23/26 – 08/30/26: From $1,720
    23

    Su

  • ORD–POP, 08/24/26 – 08/31/26: From $1,715
    24

    Mo

  • CHI–POP, 08/25/26 – 09/01/26: From $978
    25

    Tu

  • ORD–POP, 08/26/26 – 09/02/26: From $929
    26

    We

  • CHI–POP, 08/27/26 – 09/03/26: From $745
    27

    Th

  • CHI–POP, 08/28/26 – 09/04/26: From $745
    28

    Fr

  • CHI–POP, 08/29/26 – 09/05/26: From $745
    29

    Sa

  • CHI–POP, 08/30/26 – 09/06/26: From $941
    30

    Su

  • CHI–POP, 08/31/26 – 09/07/26: From $941
    31

    Mo

  • CHI–POP, 09/01/26 – 09/08/26: From $1,153
    01

    Tu

    SEP

  • ORD–POP, 09/02/26 – 09/09/26: From $882
    02

    We

  • CHI–POP, 09/03/26 – 09/10/26: From $855
    03

    Th

  • CHI–POP, 09/04/26 – 09/11/26: From $664
    04

    Fr

  • CHI–POP, 09/05/26 – 09/12/26: From $703
    05

    Sa

  • ORD–POP, 09/06/26 – 09/13/26: From $899
    06

    Su

  • CHI–POP, 09/07/26 – 09/14/26: From $894
    07

    Mo

  • CHI–POP, 09/08/26 – 09/15/26: From $745
    08

    Tu

  • CHI–POP, 09/09/26 – 09/16/26: From $860
    09

    We

  • CHI–POP, 09/10/26 – 09/17/26: From $664
    10

    Th

  • CHI–POP, 09/11/26 – 09/18/26: From $664
    11

    Fr

  • CHI–POP, 09/12/26 – 09/19/26: From $664
    12

    Sa

  • ORD–POP, 09/13/26 – 09/20/26: From $669
    13

    Su

    • range$664-$1,775

    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 Puerto Plata flights

    $
    keyboard_arrow_down

    Chicago (ORD)to

    Puerto Plata (POP)
    09/22/26 - 09/29/26

    Round trip

    Economy

    from
    $630Fare subject to changes
    Updated: 8 hours ago

    Chicago (ORD)to

    Puerto Plata (POP)
    12/08/26 - 12/15/26

    Round trip

    Economy

    from
    $630Fare subject to changes
    Updated: 8 hours ago

    Chicago (ORD)to

    Puerto Plata (POP)
    12/01/26 - 12/08/26

    Round trip

    Economy

    from
    $630Fare subject to changes
    Updated: 8 hours ago

    Chicago (ORD)to

    Puerto Plata (POP)
    10/06/26 - 10/13/26

    Round trip

    Economy

    from
    $630Fare subject to changes
    Updated: 8 hours ago

    Chicago (ORD)to

    Puerto Plata (POP)
    10/13/26 - 10/20/26

    Round trip

    Economy

    from
    $630Fare subject to changes
    Updated: 8 hours ago

    Chicago (ORD)to

    Puerto Plata (POP)
    10/20/26 - 10/27/26

    Round trip

    Economy

    from
    $630Fare subject to changes
    Updated: 8 hours ago

    Chicago (ORD)to

    Puerto Plata (POP)
    09/29/26 - 10/06/26

    Round trip

    Economy

    from
    $630Fare subject to changes
    Updated: 8 hours ago

    Chicago (ORD)to

    Puerto Plata (POP)
    11/10/26 - 11/17/26

    Round trip

    Economy

    from
    $635Fare 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 Puerto Plata

    Looking for lower fares on your trip from Chicago to Puerto Plata? 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 Puerto Plata