American Airlines flights from Chicago to Basseterre, St. Kitts

Recent searches for flights from Chicago to Basseterre, St. Kitts

Sep 2026
From$799*
Updated: 9 hours ago
Round tripIEconomy
Oct 2026
From$739*
Updated: 10 hours ago
Round tripIEconomy
Nov 2026
From$739*
Updated: 10 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $799
cmp-daily-histogram-bars-legend-max-price-aria-label $2.0K
Displaying fares for September-2026
  • CHI–SKB: cmp-view-offers-disclaimer. Find Offers
    01

    Tu

    SEP

  • ORD–SKB, 09/02/26 – 09/09/26: From $1,362
    02

    We

  • ORD–SKB, 09/03/26 – 09/10/26: From $1,598
    03

    Th

  • ORD–SKB, 09/04/26 – 09/11/26: From $2,025
    04

    Fr

  • ORD–SKB, 09/05/26 – 09/12/26: From $2,010
    05

    Sa

  • CHI–SKB, 09/06/26 – 09/13/26: From $1,347
    06

    Su

  • CHI–SKB, 09/07/26 – 09/14/26: From $1,169
    07

    Mo

  • CHI–SKB, 09/08/26 – 09/15/26: From $1,357
    08

    Tu

  • CHI–SKB, 09/09/26 – 09/16/26: From $1,024
    09

    We

  • ORD–SKB, 09/10/26 – 09/17/26: From $1,114
    10

    Th

  • ORD–SKB, 09/11/26 – 09/18/26: From $1,114
    11

    Fr

  • ORD–SKB, 09/12/26 – 09/18/26: From $1,019
    12

    Sa

  • CHI–SKB, 09/13/26 – 09/20/26: From $1,059
    13

    Su

  • CHI–SKB, 09/14/26 – 09/21/26: From $1,054
    14

    Mo

  • ORD–SKB, 09/15/26 – 09/22/26: From $909
    15

    Tu

  • CHI–SKB, 09/16/26 – 09/23/26: From $914
    16

    We

  • ORD–SKB, 09/17/26 – 09/24/26: From $944
    17

    Th

  • ORD–SKB, 09/18/26 – 09/25/26: From $944
    18

    Fr

  • CHI–SKB, 09/19/26 – 09/26/26: From $944
    19

    Sa

  • ORD–SKB, 09/20/26 – 09/27/26: From $949
    20

    Su

  • CHI–SKB, 09/21/26 – 09/28/26: From $944
    21

    Mo

  • CHI–SKB, 09/22/26 – 09/29/26: From $829
    22

    Tu

  • CHI–SKB, 09/23/26 – 09/30/26: From $834
    23

    We

  • CHI–SKB, 09/24/26 – 10/01/26: From $864
    24

    Th

  • ORD–SKB, 09/25/26 – 10/02/26: From $864
    25

    Fr

  • ORD–SKB, 09/26/26 – 10/03/26: From $864
    26

    Sa

  • ORD–SKB, 09/27/26 – 10/04/26: From $869
    27

    Su

  • ORD–SKB, 09/28/26 – 10/05/26: From $864
    28

    Mo

  • ORD–SKB, 09/29/26 – 10/06/26: From $799
    29

    Tu

  • ORD–SKB, 09/30/26 – 10/07/26: From $804
    30

    We

    • range$799-$2,025

    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 Basseterre, St. Kitts flights

    $
    keyboard_arrow_down

    Chicago (ORD)to

    Basseterre, St. Kitts (SKB)
    11/17/26 - 11/24/26

    Round trip

    Economy

    from
    $739Fare subject to changes
    Updated: 9 hours ago

    Chicago (ORD)to

    Basseterre, St. Kitts (SKB)
    10/27/26 - 11/03/26

    Round trip

    Economy

    from
    $739Fare subject to changes
    Updated: 9 hours ago

    Chicago (ORD)to

    Basseterre, St. Kitts (SKB)
    11/03/26 - 11/10/26

    Round trip

    Economy

    from
    $739Fare subject to changes
    Updated: 9 hours ago

    Chicago (ORD)to

    Basseterre, St. Kitts (SKB)
    11/10/26 - 11/17/26

    Round trip

    Economy

    from
    $739Fare subject to changes
    Updated: 9 hours ago

    Chicago (ORD)to

    Basseterre, St. Kitts (SKB)
    12/01/26 - 12/08/26

    Round trip

    Economy

    from
    $739Fare subject to changes
    Updated: 9 hours ago

    Chicago (ORD)to

    Basseterre, St. Kitts (SKB)
    12/08/26 - 12/15/26

    Round trip

    Economy

    from
    $739Fare subject to changes
    Updated: 9 hours ago

    Chicago (ORD)to

    Basseterre, St. Kitts (SKB)
    12/15/26 - 12/22/26

    Round trip

    Economy

    from
    $739Fare subject to changes
    Updated: 9 hours ago

    Chicago (ORD)to

    Basseterre, St. Kitts (SKB)
    11/11/26 - 11/18/26

    Round trip

    Economy

    from
    $744Fare subject to changes
    Updated: 9 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 Basseterre, St. Kitts

    Looking for lower fares on your trip from Chicago to Basseterre, St. Kitts? 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 Basseterre, St. Kitts