American Airlines flights from Chicago to Aspen

Recent searches for flights from Chicago to Aspen

Aug 2026
From$449*
Updated: 7 hours ago
Round tripIEconomy
Sep 2026
From$373*
Updated: 7 hours ago
Round tripIEconomy
Oct 2026
From$373*
Updated: 7 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $444
cmp-daily-histogram-bars-legend-max-price-aria-label $800
Displaying fares for August-2026
  • ORD–ASE, 08/12/26 – 08/19/26: From $537
    12

    We

    AUG

  • ORD–ASE, 08/13/26 – 08/20/26: From $527
    13

    Th

  • ORD–ASE, 08/14/26 – 08/21/26: From $527
    14

    Fr

  • ORD–ASE, 08/15/26 – 08/22/26: From $605
    15

    Sa

  • ORD–ASE, 08/16/26 – 08/23/26: From $685
    16

    Su

  • ORD–ASE, 08/17/26 – 08/24/26: From $650
    17

    Mo

  • ORD–ASE, 08/18/26 – 08/25/26: From $483
    18

    Tu

  • ORD–ASE, 08/19/26 – 08/26/26: From $537
    19

    We

  • ORD–ASE, 08/20/26 – 08/27/26: From $527
    20

    Th

  • ORD–ASE, 08/21/26 – 08/28/26: From $527
    21

    Fr

  • ORD–ASE, 08/22/26 – 08/29/26: From $572
    22

    Sa

  • ORD–ASE, 08/23/26 – 08/30/26: From $527
    23

    Su

  • ORD–ASE, 08/24/26 – 08/31/26: From $494
    24

    Mo

  • ORD–ASE, 08/25/26 – 09/01/26: From $449
    25

    Tu

  • ORD–ASE, 08/26/26 – 09/02/26: From $494
    26

    We

  • ORD–ASE, 08/27/26 – 09/03/26: From $494
    27

    Th

  • ORD–ASE, 08/28/26 – 09/04/26: From $494
    28

    Fr

  • ORD–ASE, 08/29/26 – 09/05/26: From $529
    29

    Sa

  • ORD–ASE, 08/30/26 – 09/06/26: From $484
    30

    Su

  • ORD–ASE, 08/31/26 – 09/07/26: From $800
    31

    Mo

  • ORD–ASE, 09/01/26 – 09/03/26: From $449
    01

    Tu

    SEP

  • ORD–ASE, 09/02/26 – 09/09/26: From $484
    02

    We

  • ORD–ASE, 09/03/26 – 09/10/26: From $499
    03

    Th

  • ORD–ASE, 09/04/26 – 09/11/26: From $446
    04

    Fr

  • ORD–ASE, 09/05/26 – 09/12/26: From $517
    05

    Sa

  • ORD–ASE, 09/06/26 – 09/13/26: From $482
    06

    Su

  • ORD–ASE, 09/07/26 – 09/14/26: From $482
    07

    Mo

  • ORD–ASE: cmp-view-offers-disclaimer. Find Offers
    08

    Tu

  • ORD–ASE, 09/09/26 – 09/13/26: From $517
    09

    We

  • ORD–ASE, 09/10/26 – 09/13/26: From $515
    10

    Th

  • ORD–ASE, 09/11/26 – 09/18/26: From $444
    11

    Fr

    • range$444-$800

    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 Aspen flights

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    Chicago (ORD)to

    Aspen (ASE)
    10/06/26 - 10/13/26

    Round trip

    Economy

    from
    $373Fare subject to changes
    Updated: 7 hours ago

    Chicago (ORD)to

    Aspen (ASE)
    09/29/26 - 10/06/26

    Round trip

    Economy

    from
    $373Fare subject to changes
    Updated: 7 hours ago

    Chicago (ORD)to

    Aspen (ASE)
    10/20/26 - 10/27/26

    Round trip

    Economy

    from
    $373Fare subject to changes
    Updated: 7 hours ago

    Chicago (ORD)to

    Aspen (ASE)
    10/13/26 - 10/20/26

    Round trip

    Economy

    from
    $373Fare subject to changes
    Updated: 7 hours ago

    Chicago (ORD)to

    Aspen (ASE)
    09/15/26 - 09/22/26

    Round trip

    Economy

    from
    $373Fare subject to changes
    Updated: 7 hours ago

    Chicago (ORD)to

    Aspen (ASE)
    09/22/26 - 09/29/26

    Round trip

    Economy

    from
    $373Fare subject to changes
    Updated: 7 hours ago

    Chicago (ORD)to

    Aspen (ASE)
    10/27/26 - 11/03/26

    Round trip

    Economy

    from
    $383Fare subject to changes
    Updated: 7 hours ago

    Chicago (ORD)to

    Aspen (ASE)
    11/03/26 - 11/10/26

    Round trip

    Economy

    from
    $393Fare subject to changes
    Updated: 7 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 Aspen

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