American Airlines flights from Lexington to Chicago

Recent searches for flights from Lexington to Chicago

Aug 2026
From$421*
Updated: 3 hours ago
Round tripIEconomy
Sep 2026
From$279*
Updated: 3 hours ago
Round tripIEconomy
Oct 2026
From$279*
Updated: 3 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $279
cmp-daily-histogram-bars-legend-max-price-aria-label $421
Displaying fares for August-2026
  • LEX–ORD, 08/30/26 – 09/06/26: From $421
    30

    Su

    AUG

  • LEX–ORD, 08/31/26 – 09/07/26: From $421
    31

    Mo

  • LEX–ORD, 09/01/26 – 09/08/26: From $382
    01

    Tu

    SEP

  • LEX–ORD, 09/02/26 – 09/09/26: From $382
    02

    We

  • LEX–ORD, 09/03/26 – 09/10/26: From $421
    03

    Th

  • LEX–ORD, 09/04/26 – 09/11/26: From $421
    04

    Fr

  • LEX–ORD, 09/05/26 – 09/07/26: From $347
    05

    Sa

  • LEX–ORD, 09/06/26 – 09/13/26: From $317
    06

    Su

  • LEX–ORD, 09/07/26 – 09/14/26: From $339
    07

    Mo

  • LEX–ORD, 09/08/26 – 09/15/26: From $339
    08

    Tu

  • LEX–ORD, 09/09/26 – 09/16/26: From $317
    09

    We

  • LEX–ORD, 09/10/26 – 09/17/26: From $317
    10

    Th

  • LEX–ORD, 09/11/26 – 09/18/26: From $317
    11

    Fr

  • LEX–ORD, 09/12/26 – 09/19/26: From $317
    12

    Sa

  • LEX–ORD, 09/13/26 – 09/20/26: From $294
    13

    Su

  • LEX–ORD, 09/14/26 – 09/21/26: From $294
    14

    Mo

  • LEX–ORD, 09/15/26 – 09/22/26: From $294
    15

    Tu

  • LEX–ORD, 09/16/26 – 09/23/26: From $294
    16

    We

  • LEX–ORD, 09/17/26 – 09/24/26: From $294
    17

    Th

  • LEX–ORD, 09/18/26 – 09/25/26: From $294
    18

    Fr

  • LEX–ORD, 09/19/26 – 09/26/26: From $294
    19

    Sa

  • LEX–ORD, 09/20/26 – 09/27/26: From $279
    20

    Su

  • LEX–ORD, 09/21/26 – 09/28/26: From $279
    21

    Mo

  • LEX–ORD, 09/22/26 – 09/29/26: From $279
    22

    Tu

  • LEX–ORD, 09/23/26 – 09/30/26: From $279
    23

    We

  • LEX–ORD, 09/24/26 – 10/01/26: From $279
    24

    Th

  • LEX–ORD, 09/25/26 – 10/02/26: From $279
    25

    Fr

  • LEX–ORD, 09/26/26 – 10/03/26: From $279
    26

    Sa

  • LEX–ORD: cmp-view-offers-disclaimer. Find Offers
    27

    Su

  • LEX–ORD: cmp-view-offers-disclaimer. Find Offers
    28

    Mo

  • LEX–ORD, 09/29/26 – 10/06/26: From $279
    29

    Tu

    • range$279-$421

    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 Lexington to Chicago flights

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    Lexington (LEX)to

    Chicago (ORD)
    10/29/26 - 11/05/26

    Round trip

    Economy

    from
    $279Fare subject to changes
    Updated: 21 hours ago

    Lexington (LEX)to

    Chicago (ORD)
    10/06/26 - 10/13/26

    Round trip

    Economy

    from
    $279Fare subject to changes
    Updated: 3 hours ago

    Lexington (LEX)to

    Chicago (ORD)
    10/07/26 - 10/14/26

    Round trip

    Economy

    from
    $279Fare subject to changes
    Updated: 3 hours ago

    Lexington (LEX)to

    Chicago (ORD)
    10/08/26 - 10/15/26

    Round trip

    Economy

    from
    $279Fare subject to changes
    Updated: 3 hours ago

    Lexington (LEX)to

    Chicago (ORD)
    10/13/26 - 10/20/26

    Round trip

    Economy

    from
    $279Fare subject to changes
    Updated: 3 hours ago

    Lexington (LEX)to

    Chicago (ORD)
    10/15/26 - 10/22/26

    Round trip

    Economy

    from
    $279Fare subject to changes
    Updated: 3 hours ago

    Lexington (LEX)to

    Chicago (ORD)
    10/23/26 - 10/30/26

    Round trip

    Economy

    from
    $279Fare subject to changes
    Updated: 3 hours ago

    Lexington (LEX)to

    Chicago (ORD)
    09/20/26 - 09/27/26

    Round trip

    Economy

    from
    $279Fare subject to changes
    Updated: 3 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 Lexington to Chicago

    Looking for lower fares on your trip from Lexington to Chicago? 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 Lexington to Chicago