American Airlines flights from Houston to Chicago

Recent searches for flights from Houston to Chicago

Aug 2026
From$457*
Updated: 4 hours ago
Round tripIEconomy
Sep 2026
From$209*
Updated: 14 hours ago
Round tripIEconomy
Oct 2026
From$209*
Updated: 14 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $209
cmp-daily-histogram-bars-legend-max-price-aria-label $596
Displaying fares for August-2026
  • IAH–ORD, 08/23/26 – 08/26/26: From $545
    23

    Su

    AUG

  • IAH–ORD, 08/24/26 – 08/25/26: From $519
    24

    Mo

  • IAH–ORD, 08/25/26 – 09/01/26: From $457
    25

    Tu

  • IAH–ORD, 08/26/26 – 09/02/26: From $457
    26

    We

  • IAH–CHI, 08/27/26 – 09/03/26: From $553
    27

    Th

  • IAH–CHI, 08/28/26 – 09/04/26: From $553
    28

    Fr

  • IAH–CHI, 08/29/26 – 09/05/26: From $457
    29

    Sa

  • IAH–ORD, 08/30/26 – 09/06/26: From $546
    30

    Su

  • IAH–ORD, 08/31/26 – 09/07/26: From $596
    31

    Mo

  • IAH–CHI, 09/01/26 – 09/08/26: From $467
    01

    Tu

    SEP

  • IAH–CHI, 09/02/26 – 09/09/26: From $457
    02

    We

  • IAH–ORD, 09/03/26 – 09/10/26: From $546
    03

    Th

  • IAH–CHI, 09/04/26 – 09/11/26: From $546
    04

    Fr

  • IAH–ORD, 09/05/26 – 09/12/26: From $404
    05

    Sa

  • IAH–CHI, 09/06/26 – 09/13/26: From $367
    06

    Su

  • IAH–CHI, 09/07/26 – 09/14/26: From $414
    07

    Mo

  • IAH–CHI, 09/08/26 – 09/15/26: From $333
    08

    Tu

  • IAH–CHI, 09/09/26 – 09/16/26: From $280
    09

    We

  • IAH–ORD, 09/10/26 – 09/17/26: From $280
    10

    Th

  • IAH–ORD, 09/11/26 – 09/18/26: From $293
    11

    Fr

  • IAH–ORD, 09/12/26 – 09/15/26: From $209
    12

    Sa

  • IAH–CHI, 09/13/26 – 09/20/26: From $383
    13

    Su

  • IAH–CHI, 09/14/26 – 09/21/26: From $209
    14

    Mo

  • IAH–CHI, 09/15/26 – 09/22/26: From $209
    15

    Tu

  • IAH–CHI, 09/16/26 – 09/23/26: From $209
    16

    We

  • IAH–CHI, 09/17/26 – 09/24/26: From $209
    17

    Th

  • IAH–ORD, 09/18/26 – 09/21/26: From $222
    18

    Fr

  • IAH–CHI, 09/19/26 – 09/26/26: From $209
    19

    Sa

  • IAH–CHI: cmp-view-offers-disclaimer. Find Offers
    20

    Su

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

    Mo

  • IAH–ORD, 09/22/26 – 09/29/26: From $209
    22

    Tu

    • range$209-$596

    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 Houston to Chicago flights

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    Houston (IAH)to

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

    Round trip

    Economy

    from
    $209Fare subject to changes
    Updated: 4 hours ago

    Houston (IAH)to

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

    Round trip

    Economy

    from
    $209Fare subject to changes
    Updated: 4 hours ago

    Houston (IAH)to

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

    Round trip

    Economy

    from
    $209Fare subject to changes
    Updated: 4 hours ago

    Houston (IAH)to

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

    Round trip

    Economy

    from
    $209Fare subject to changes
    Updated: 4 hours ago

    Houston (IAH)to

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

    Round trip

    Economy

    from
    $209Fare subject to changes
    Updated: 4 hours ago

    Houston (IAH)to

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

    Round trip

    Economy

    from
    $209Fare subject to changes
    Updated: 4 hours ago

    Houston (IAH)to

    Chicago (ORD)
    09/14/26 - 09/21/26

    Round trip

    Economy

    from
    $209Fare subject to changes
    Updated: 4 hours ago

    Houston (IAH)to

    Chicago (ORD)
    09/16/26 - 09/23/26

    Round trip

    Economy

    from
    $209Fare subject to changes
    Updated: 4 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 Houston to Chicago

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