American Airlines flights from Chicago to St. Thomas

Recent searches for flights from Chicago to St. Thomas

Aug 2026
From$650*
Updated: 17 hours ago
Round tripIEconomy
Sep 2026
From$585*
Updated: 17 hours ago
Round tripIEconomy
Oct 2026
From$580*
Updated: 17 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $650
cmp-daily-histogram-bars-legend-max-price-aria-label $2.0K
Displaying fares for August-2026
  • ORD–STT, 08/06/26 – 08/13/26: From $2,033
    06

    Th

    AUG

  • ORD–STT, 08/07/26 – 08/14/26: From $2,044
    07

    Fr

  • ORD–STT, 08/08/26 – 08/15/26: From $1,682
    08

    Sa

  • ORD–STT, 08/09/26 – 08/16/26: From $1,476
    09

    Su

  • ORD–STT, 08/10/26 – 08/17/26: From $1,461
    10

    Mo

  • ORD–STT, 08/11/26 – 08/18/26: From $1,315
    11

    Tu

  • ORD–STT, 08/12/26 – 08/19/26: From $1,270
    12

    We

  • ORD–STT, 08/13/26 – 08/20/26: From $1,241
    13

    Th

  • ORD–STT, 08/14/26 – 08/21/26: From $1,284
    14

    Fr

  • ORD–STT, 08/15/26 – 08/22/26: From $1,063
    15

    Sa

  • ORD–STT, 08/16/26 – 08/23/26: From $1,241
    16

    Su

  • ORD–STT, 08/17/26 – 08/24/26: From $1,089
    17

    Mo

  • ORD–STT, 08/18/26 – 08/25/26: From $1,210
    18

    Tu

  • ORD–STT, 08/19/26 – 08/26/26: From $1,064
    19

    We

  • ORD–STT, 08/20/26 – 08/27/26: From $1,170
    20

    Th

  • ORD–STT, 08/21/26 – 08/28/26: From $1,011
    21

    Fr

  • ORD–STT, 08/22/26 – 08/29/26: From $1,153
    22

    Sa

  • ORD–STT, 08/23/26 – 08/30/26: From $1,198
    23

    Su

  • ORD–STT, 08/24/26 – 08/31/26: From $1,124
    24

    Mo

  • ORD–STT, 08/25/26 – 09/01/26: From $810
    25

    Tu

  • ORD–STT, 08/26/26 – 09/02/26: From $770
    26

    We

  • ORD–STT, 08/27/26 – 09/03/26: From $650
    27

    Th

  • ORD–STT, 08/28/26 – 09/04/26: From $650
    28

    Fr

  • ORD–STT, 08/29/26 – 09/05/26: From $675
    29

    Sa

  • ORD–STT, 08/30/26 – 09/06/26: From $710
    30

    Su

  • ORD–STT, 08/31/26 – 09/07/26: From $850
    31

    Mo

  • ORD–STT, 09/01/26 – 09/08/26: From $1,025
    01

    Tu

    SEP

  • ORD–STT, 09/02/26 – 09/09/26: From $942
    02

    We

  • ORD–STT: cmp-view-offers-disclaimer. Find Offers
    03

    Th

  • ORD–STT: cmp-view-offers-disclaimer. Find Offers
    04

    Fr

  • ORD–STT, 09/05/26 – 09/12/26: From $830
    05

    Sa

    • range$650-$2,044

    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 St. Thomas flights

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    Chicago (ORD)to

    St. Thomas (STT)
    01/07/27 - 01/12/27

    Round trip

    Economy

    from
    $576Fare subject to changes
    Updated: 35 minutes ago

    Chicago (ORD)to

    St. Thomas (STT)
    01/14/27 - 01/21/27

    Round trip

    Economy

    from
    $576Fare subject to changes
    Updated: 16 hours ago

    Chicago (ORD)to

    St. Thomas (STT)
    04/04/27 - 04/16/27

    Round trip

    Economy

    from
    $576Fare subject to changes
    Updated: 20 hours ago

    Chicago (ORD)to

    St. Thomas (STT)
    02/19/27 - 02/26/27

    Round trip

    Economy

    from
    $576Fare subject to changes
    Updated: 19 hours ago

    Chicago (ORD)to

    St. Thomas (STT)
    10/18/26 - 10/25/26

    Round trip

    Economy

    from
    $580Fare subject to changes
    Updated: 17 hours ago

    Chicago (ORD)to

    St. Thomas (STT)
    10/20/26 - 10/27/26

    Round trip

    Economy

    from
    $580Fare subject to changes
    Updated: 17 hours ago

    Chicago (ORD)to

    St. Thomas (STT)
    10/26/26 - 11/02/26

    Round trip

    Economy

    from
    $580Fare subject to changes
    Updated: 17 hours ago

    Chicago (ORD)to

    St. Thomas (STT)
    10/30/26 - 11/06/26

    Round trip

    Economy

    from
    $580Fare subject to changes
    Updated: 17 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 St. Thomas

    Looking for lower fares on your trip from Chicago to St. Thomas? 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 St. Thomas