American Airlines flights from Monterey to Chicago

Recent searches for flights from Monterey to Chicago

Aug 2026
From$359*
Updated: 14 hours ago
Round tripIEconomy
Sep 2026
From$359*
Updated: 14 hours ago
Round tripIEconomy
Oct 2026
From$359*
Updated: 14 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $359
cmp-daily-histogram-bars-legend-max-price-aria-label $1.6K
Displaying fares for August-2026
  • MRY–ORD, 08/05/26 – 08/12/26: From $737
    05

    We

    AUG

  • MRY–ORD, 08/06/26 – 08/13/26: From $737
    06

    Th

  • MRY–ORD, 08/07/26 – 08/14/26: From $554
    07

    Fr

  • MRY–ORD, 08/08/26 – 08/15/26: From $554
    08

    Sa

  • MRY–ORD, 08/09/26 – 08/16/26: From $554
    09

    Su

  • MRY–ORD, 08/10/26 – 08/17/26: From $554
    10

    Mo

  • MRY–ORD, 08/11/26 – 08/18/26: From $474
    11

    Tu

  • MRY–ORD, 08/12/26 – 08/19/26: From $474
    12

    We

  • MRY–ORD, 08/13/26 – 08/20/26: From $702
    13

    Th

  • MRY–ORD, 08/14/26 – 08/21/26: From $474
    14

    Fr

  • MRY–ORD, 08/15/26 – 08/22/26: From $474
    15

    Sa

  • MRY–ORD, 08/16/26 – 08/23/26: From $704
    16

    Su

  • MRY–ORD, 08/17/26 – 08/24/26: From $1,578
    17

    Mo

  • MRY–ORD, 08/18/26 – 08/25/26: From $394
    18

    Tu

  • MRY–ORD, 08/19/26 – 08/26/26: From $394
    19

    We

  • MRY–ORD, 08/20/26 – 08/27/26: From $643
    20

    Th

  • MRY–ORD, 08/21/26 – 08/28/26: From $394
    21

    Fr

  • MRY–ORD, 08/22/26 – 08/29/26: From $394
    22

    Sa

  • MRY–ORD, 08/23/26 – 08/30/26: From $622
    23

    Su

  • MRY–ORD, 08/24/26 – 08/31/26: From $394
    24

    Mo

  • MRY–ORD, 08/25/26 – 09/01/26: From $359
    25

    Tu

  • MRY–ORD, 08/26/26 – 09/02/26: From $359
    26

    We

  • MRY–ORD, 08/27/26 – 09/03/26: From $608
    27

    Th

  • MRY–ORD, 08/28/26 – 09/04/26: From $608
    28

    Fr

  • MRY–ORD, 08/29/26 – 09/05/26: From $359
    29

    Sa

  • MRY–ORD, 08/30/26 – 09/06/26: From $359
    30

    Su

  • MRY–ORD, 08/31/26 – 09/07/26: From $757
    31

    Mo

  • MRY–ORD: cmp-view-offers-disclaimer. Find Offers
    01

    Tu

    SEP

  • MRY–ORD: cmp-view-offers-disclaimer. Find Offers
    02

    We

  • MRY–ORD, 09/03/26 – 09/08/26: From $359
    03

    Th

  • MRY–ORD, 09/04/26 – 09/11/26: From $359
    04

    Fr

    • range$359-$1,578

    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 Monterey to Chicago flights

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    Monterey (MRY)to

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

    Round trip

    Economy

    from
    $359Fare subject to changes
    Updated: 14 hours ago

    Monterey (MRY)to

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

    Round trip

    Economy

    from
    $359Fare subject to changes
    Updated: 14 hours ago

    Monterey (MRY)to

    Chicago (ORD)
    10/22/26 - 10/29/26

    Round trip

    Economy

    from
    $359Fare subject to changes
    Updated: 14 hours ago

    Monterey (MRY)to

    Chicago (ORD)
    10/26/26 - 11/02/26

    Round trip

    Economy

    from
    $359Fare subject to changes
    Updated: 14 hours ago

    Monterey (MRY)to

    Chicago (ORD)
    09/04/26 - 09/11/26

    Round trip

    Economy

    from
    $359Fare subject to changes
    Updated: 14 hours ago

    Monterey (MRY)to

    Chicago (ORD)
    09/05/26 - 09/12/26

    Round trip

    Economy

    from
    $359Fare subject to changes
    Updated: 14 hours ago

    Monterey (MRY)to

    Chicago (ORD)
    09/12/26 - 09/19/26

    Round trip

    Economy

    from
    $359Fare subject to changes
    Updated: 14 hours ago

    Monterey (MRY)to

    Chicago (ORD)
    09/21/26 - 09/28/26

    Round trip

    Economy

    from
    $359Fare subject to changes
    Updated: 14 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 Monterey to Chicago

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