American Airlines flights from Denver to Chicago

Recent searches for flights from Denver to Chicago

Aug 2026
From$437*
Updated: 10 hours ago
Round tripIEconomy
Sep 2026
From$213*
Updated: 9 hours ago
Round tripIEconomy
Oct 2026
From$213*
Updated: 10 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $213
cmp-daily-histogram-bars-legend-max-price-aria-label $553
Displaying fares for August-2026
  • DEN–ORD, 08/25/26 – 09/01/26: From $437
    25

    Tu

    AUG

  • DEN–CHI, 08/26/26 – 09/02/26: From $437
    26

    We

  • DEN–ORD, 08/27/26 – 09/03/26: From $553
    27

    Th

  • DEN–ORD, 08/28/26 – 09/04/26: From $553
    28

    Fr

  • DEN–CHI, 08/29/26 – 09/05/26: From $437
    29

    Sa

  • DEN–CHI, 08/30/26 – 09/06/26: From $553
    30

    Su

  • DEN–ORD, 08/31/26 – 09/07/26: From $525
    31

    Mo

  • DEN–ORD, 09/01/26 – 09/16/26: From $345
    01

    Tu

    SEP

  • DEN–CHI, 09/02/26 – 09/09/26: From $427
    02

    We

  • DEN–ORD, 09/03/26 – 10/01/26: From $433
    03

    Th

  • DEN–ORD, 09/04/26 – 09/07/26: From $433
    04

    Fr

  • DEN–ORD, 09/05/26 – 09/07/26: From $339
    05

    Sa

  • DEN–CHI, 09/06/26 – 09/13/26: From $374
    06

    Su

  • DEN–ORD, 09/07/26 – 09/14/26: From $315
    07

    Mo

  • DEN–ORD, 09/08/26 – 09/15/26: From $315
    08

    Tu

  • DEN–ORD, 09/09/26 – 09/16/26: From $272
    09

    We

  • DEN–CHI, 09/10/26 – 09/17/26: From $272
    10

    Th

  • DEN–ORD, 09/11/26 – 09/14/26: From $272
    11

    Fr

  • DEN–ORD, 09/12/26 – 09/19/26: From $272
    12

    Sa

  • DEN–ORD, 09/13/26 – 09/20/26: From $376
    13

    Su

  • DEN–ORD, 09/14/26 – 09/21/26: From $213
    14

    Mo

  • DEN–CHI, 09/15/26 – 09/22/26: From $213
    15

    Tu

  • DEN–ORD, 09/16/26 – 09/23/26: From $213
    16

    We

  • DEN–ORD, 09/17/26 – 09/24/26: From $213
    17

    Th

  • DEN–CHI, 09/18/26 – 09/28/26: From $225
    18

    Fr

  • DEN–CHI, 09/19/26 – 09/26/26: From $213
    19

    Sa

  • DEN–CHI, 09/20/26 – 09/27/26: From $305
    20

    Su

  • DEN–CHI: cmp-view-offers-disclaimer. Find Offers
    21

    Mo

  • DEN–CHI: cmp-view-offers-disclaimer. Find Offers
    22

    Tu

  • DEN–ORD, 09/23/26 – 09/27/26: From $244
    23

    We

  • DEN–CHI, 09/24/26 – 10/01/26: From $213
    24

    Th

    • range$213-$553

    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 Denver to Chicago flights

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    Denver (DEN)to

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

    Round trip

    Economy

    from
    $213Fare subject to changes
    Updated: 10 hours ago

    Denver (DEN)to

    Chicago (ORD)
    10/05/26 - 10/12/26

    Round trip

    Economy

    from
    $213Fare subject to changes
    Updated: 10 hours ago

    Denver (DEN)to

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

    Round trip

    Economy

    from
    $213Fare subject to changes
    Updated: 10 hours ago

    Denver (DEN)to

    Chicago (ORD)
    10/28/26 - 11/04/26

    Round trip

    Economy

    from
    $213Fare subject to changes
    Updated: 10 hours ago

    Denver (DEN)to

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

    Round trip

    Economy

    from
    $213Fare subject to changes
    Updated: 10 hours ago

    Denver (DEN)to

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

    Round trip

    Economy

    from
    $213Fare subject to changes
    Updated: 10 hours ago

    Denver (DEN)to

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

    Round trip

    Economy

    from
    $213Fare subject to changes
    Updated: 10 hours ago

    Denver (DEN)to

    Chicago (ORD)
    10/17/26 - 10/24/26

    Round trip

    Economy

    from
    $213Fare subject to changes
    Updated: 10 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 Denver to Chicago

    Looking for lower fares on your trip from Denver 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 Denver to Chicago