American Airlines flights from New York to Chicago

Recent searches for flights from New York to Chicago

Aug 2026
From$285*
Updated: 4 hours ago
Round tripIEconomy
Sep 2026
From$242*
Updated: 5 hours ago
Round tripIEconomy
Oct 2026
From$247*
Updated: 13 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $242
cmp-daily-histogram-bars-legend-max-price-aria-label $438
Displaying fares for August-2026
  • LGA–ORD, 08/23/26 – 08/25/26: From $310
    23

    Su

    AUG

  • LGA–CHI, 08/24/26 – 08/31/26: From $335
    24

    Mo

  • LGA–CHI, 08/25/26 – 09/01/26: From $285
    25

    Tu

  • LGA–ORD, 08/26/26 – 09/02/26: From $285
    26

    We

  • NYC–ORD, 08/27/26 – 08/29/26: From $310
    27

    Th

  • JFK–ORD, 08/28/26 – 08/31/26: From $335
    28

    Fr

  • NYC–ORD, 08/29/26 – 09/05/26: From $287
    29

    Sa

  • LGA–CHI, 08/30/26 – 09/06/26: From $306
    30

    Su

  • NYC–ORD, 08/31/26 – 09/07/26: From $438
    31

    Mo

  • NYC–CHI, 09/01/26 – 09/08/26: From $287
    01

    Tu

    SEP

  • LGA–ORD, 09/02/26 – 09/06/26: From $281
    02

    We

  • NYC–ORD, 09/03/26 – 09/08/26: From $292
    03

    Th

  • NYC–ORD, 09/04/26 – 09/08/26: From $306
    04

    Fr

  • NYC–ORD, 09/05/26 – 09/14/26: From $262
    05

    Sa

  • NYC–CHI, 09/06/26 – 09/13/26: From $262
    06

    Su

  • NYC–CHI, 09/07/26 – 09/14/26: From $262
    07

    Mo

  • LGA–ORD, 09/08/26 – 09/15/26: From $242
    08

    Tu

  • JFK–ORD, 09/09/26 – 09/16/26: From $266
    09

    We

  • NYC–ORD, 09/10/26 – 09/17/26: From $271
    10

    Th

  • NYC–CHI, 09/11/26 – 09/18/26: From $271
    11

    Fr

  • NYC–ORD, 09/12/26 – 09/19/26: From $266
    12

    Sa

  • NYC–ORD, 09/13/26 – 09/20/26: From $247
    13

    Su

  • NYC–ORD, 09/14/26 – 09/21/26: From $247
    14

    Mo

  • LGA–CHI, 09/15/26 – 09/22/26: From $247
    15

    Tu

  • JFK–ORD, 09/16/26 – 09/23/26: From $247
    16

    We

  • NYC–CHI, 09/17/26 – 09/24/26: From $247
    17

    Th

  • LGA–ORD, 09/18/26 – 09/25/26: From $247
    18

    Fr

  • NYC–ORD, 09/19/26 – 09/26/26: From $247
    19

    Sa

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

    Su

  • NYC–CHI, 09/21/26 – 09/24/26: From $247
    21

    Mo

  • LGA–CHI, 09/22/26 – 09/29/26: From $247
    22

    Tu

    • range$242-$438

    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 New York to Chicago flights

    $
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    New York (NYC)to

    Chicago (ORD)
    09/08/26 - 09/15/26

    Round trip

    Economy

    from
    $242Fare subject to changes
    Updated: 4 hours ago

    New York (NYC)to

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

    Round trip

    Economy

    from
    $247Fare subject to changes
    Updated: 4 hours ago

    New York (NYC)to

    Chicago (ORD)
    09/15/26 - 09/22/26

    Round trip

    Economy

    from
    $247Fare subject to changes
    Updated: 4 hours ago

    New York (NYC)to

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

    Round trip

    Economy

    from
    $247Fare subject to changes
    Updated: 4 hours ago

    New York (NYC)to

    Chicago (ORD)
    09/24/26 - 10/01/26

    Round trip

    Economy

    from
    $247Fare subject to changes
    Updated: 4 hours ago

    New York (NYC)to

    Chicago (ORD)
    09/25/26 - 10/02/26

    Round trip

    Economy

    from
    $247Fare subject to changes
    Updated: 4 hours ago

    New York (NYC)to

    Chicago (ORD)
    09/26/26 - 10/03/26

    Round trip

    Economy

    from
    $247Fare subject to changes
    Updated: 4 hours ago

    New York (NYC)to

    Chicago (ORD)
    09/28/26 - 10/05/26

    Round trip

    Economy

    from
    $247Fare 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 New York to Chicago

    Looking for lower fares on your trip from New York 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 New York to Chicago