American Airlines flights from Colorado Springs to Chicago

Recent searches for flights from Colorado Springs to Chicago

Aug 2026
From$340*
Updated: 3 hours ago
Round tripIEconomy
Sep 2026
From$221*
Updated: 3 hours ago
Round tripIEconomy
Oct 2026
From$221*
Updated: 3 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $241
cmp-daily-histogram-bars-legend-max-price-aria-label $521
Displaying fares for August-2026
  • COS–ORD, 08/12/26 – 08/19/26: From $459
    12

    We

    AUG

  • COS–ORD, 08/13/26 – 08/20/26: From $511
    13

    Th

  • COS–ORD, 08/14/26 – 08/21/26: From $511
    14

    Fr

  • COS–ORD, 08/15/26 – 08/22/26: From $459
    15

    Sa

  • COS–ORD, 08/16/26 – 08/23/26: From $521
    16

    Su

  • COS–ORD, 08/17/26 – 08/24/26: From $521
    17

    Mo

  • COS–ORD, 08/18/26 – 08/25/26: From $459
    18

    Tu

  • COS–ORD, 08/19/26 – 08/26/26: From $461
    19

    We

  • COS–ORD, 08/20/26 – 08/27/26: From $477
    20

    Th

  • COS–ORD, 08/21/26 – 08/28/26: From $477
    21

    Fr

  • COS–ORD, 08/22/26 – 08/29/26: From $451
    22

    Sa

  • COS–ORD, 08/23/26 – 08/30/26: From $477
    23

    Su

  • COS–ORD, 08/24/26 – 08/31/26: From $369
    24

    Mo

  • COS–ORD, 08/25/26 – 09/01/26: From $340
    25

    Tu

  • COS–ORD, 08/26/26 – 09/02/26: From $352
    26

    We

  • COS–ORD, 08/27/26 – 09/03/26: From $432
    27

    Th

  • COS–ORD, 08/28/26 – 09/04/26: From $379
    28

    Fr

  • COS–ORD, 08/29/26 – 09/05/26: From $352
    29

    Sa

  • COS–ORD, 08/30/26 – 09/06/26: From $353
    30

    Su

  • COS–ORD, 08/31/26 – 09/07/26: From $434
    31

    Mo

  • COS–ORD, 09/01/26 – 09/08/26: From $241
    01

    Tu

    SEP

  • COS–ORD, 09/02/26 – 09/09/26: From $261
    02

    We

  • COS–ORD, 09/03/26 – 09/10/26: From $349
    03

    Th

  • COS–ORD, 09/04/26 – 09/11/26: From $279
    04

    Fr

  • COS–ORD, 09/05/26 – 09/12/26: From $241
    05

    Sa

  • COS–ORD, 09/06/26 – 09/13/26: From $391
    06

    Su

  • COS–ORD, 09/07/26 – 09/14/26: From $457
    07

    Mo

  • COS–ORD, 09/08/26 – 09/15/26: From $331
    08

    Tu

  • COS–ORD: cmp-view-offers-disclaimer. Find Offers
    09

    We

  • COS–ORD, 09/10/26 – 09/14/26: From $244
    10

    Th

  • COS–ORD, 09/11/26 – 09/18/26: From $269
    11

    Fr

    • range$241-$521

    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 Colorado Springs to Chicago flights

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    Colorado Springs (COS)to

    Chicago (ORD)
    10/14/26 - 10/21/26

    Round trip

    Economy

    from
    $221Fare subject to changes
    Updated: 3 hours ago

    Colorado Springs (COS)to

    Chicago (ORD)
    10/27/26 - 11/03/26

    Round trip

    Economy

    from
    $221Fare subject to changes
    Updated: 3 hours ago

    Colorado Springs (COS)to

    Chicago (ORD)
    10/31/26 - 11/07/26

    Round trip

    Economy

    from
    $221Fare subject to changes
    Updated: 3 hours ago

    Colorado Springs (COS)to

    Chicago (ORD)
    09/19/26 - 09/26/26

    Round trip

    Economy

    from
    $221Fare subject to changes
    Updated: 3 hours ago

    Colorado Springs (COS)to

    Chicago (ORD)
    09/30/26 - 10/07/26

    Round trip

    Economy

    from
    $221Fare subject to changes
    Updated: 3 hours ago

    Colorado Springs (COS)to

    Chicago (ORD)
    10/20/26 - 10/27/26

    Round trip

    Economy

    from
    $221Fare subject to changes
    Updated: 3 hours ago

    Colorado Springs (COS)to

    Chicago (ORD)
    10/21/26 - 10/28/26

    Round trip

    Economy

    from
    $221Fare subject to changes
    Updated: 3 hours ago

    Colorado Springs (COS)to

    Chicago (ORD)
    10/24/26 - 10/31/26

    Round trip

    Economy

    from
    $221Fare 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 Colorado Springs to Chicago

    Looking for lower fares on your trip from Colorado Springs 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 Colorado Springs to Chicago