American Airlines flights from Chicago to Cabo San Lucas

Recent searches for flights from Chicago to Cabo San Lucas

Aug 2026
From$607*
Updated: 5 hours ago
Round tripIEconomy
Sep 2026
From$597*
Updated: 5 hours ago
Round tripIEconomy
Oct 2026
From$593*
Updated: 5 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $607
cmp-daily-histogram-bars-legend-max-price-aria-label $2.0K
Displaying fares for August-2026
  • ORD–SJD, 08/05/26 – 08/12/26: From $2,038
    05

    We

    AUG

  • ORD–SJD, 08/06/26 – 08/13/26: From $900
    06

    Th

  • ORD–SJD, 08/07/26 – 08/14/26: From $900
    07

    Fr

  • ORD–SJD, 08/08/26 – 08/15/26: From $935
    08

    Sa

  • ORD–SJD, 08/09/26 – 08/16/26: From $1,105
    09

    Su

  • ORD–SJD, 08/10/26 – 08/17/26: From $808
    10

    Mo

  • CHI–SJD, 08/11/26 – 08/18/26: From $788
    11

    Tu

  • ORD–SJD, 08/12/26 – 08/19/26: From $838
    12

    We

  • ORD–SJD, 08/13/26 – 08/20/26: From $833
    13

    Th

  • CHI–SJD, 08/14/26 – 08/21/26: From $833
    14

    Fr

  • ORD–SJD, 08/15/26 – 08/22/26: From $820
    15

    Sa

  • ORD–SJD, 08/16/26 – 08/22/26: From $798
    16

    Su

  • ORD–SJD, 08/17/26 – 08/24/26: From $830
    17

    Mo

  • CHI–SJD, 08/18/26 – 08/25/26: From $703
    18

    Tu

  • ORD–SJD, 08/19/26 – 08/26/26: From $708
    19

    We

  • CHI–SJD, 08/20/26 – 08/27/26: From $727
    20

    Th

  • ORD–SJD, 08/21/26 – 08/28/26: From $727
    21

    Fr

  • CHI–SJD, 08/22/26 – 08/27/26: From $685
    22

    Sa

  • CHI–SJD, 08/23/26 – 08/30/26: From $733
    23

    Su

  • ORD–SJD, 08/24/26 – 08/26/26: From $685
    24

    Mo

  • CHI–SJD, 08/25/26 – 09/01/26: From $607
    25

    Tu

  • CHI–SJD, 08/26/26 – 09/02/26: From $612
    26

    We

  • ORD–SJD, 08/27/26 – 09/03/26: From $668
    27

    Th

  • CHI–SJD, 08/28/26 – 09/04/26: From $668
    28

    Fr

  • ORD–SJD, 08/29/26 – 09/03/26: From $625
    29

    Sa

  • ORD–SJD, 08/30/26 – 09/05/26: From $640
    30

    Su

  • ORD–SJD, 08/31/26 – 09/05/26: From $640
    31

    Mo

  • CHI–SJD, 09/01/26 – 09/08/26: From $775
    01

    Tu

    SEP

  • ORD–SJD, 09/02/26 – 09/09/26: From $652
    02

    We

  • ORD–SJD, 09/03/26 – 09/10/26: From $680
    03

    Th

  • CHI–SJD, 09/04/26 – 09/11/26: From $675
    04

    Fr

    • range$607-$2,038

    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 Chicago to Cabo San Lucas flights

    $
    keyboard_arrow_down

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    11/10/26 - 11/17/26

    Round trip

    Economy

    from
    $593Fare subject to changes
    Updated: 5 hours ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    12/01/26 - 12/08/26

    Round trip

    Economy

    from
    $593Fare subject to changes
    Updated: 5 hours ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    10/06/26 - 10/13/26

    Round trip

    Economy

    from
    $593Fare subject to changes
    Updated: 5 hours ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    10/13/26 - 10/20/26

    Round trip

    Economy

    from
    $593Fare subject to changes
    Updated: 5 hours ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    10/20/26 - 10/27/26

    Round trip

    Economy

    from
    $593Fare subject to changes
    Updated: 5 hours ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    10/27/26 - 11/03/26

    Round trip

    Economy

    from
    $593Fare subject to changes
    Updated: 5 hours ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    11/17/26 - 11/24/26

    Round trip

    Economy

    from
    $593Fare subject to changes
    Updated: 5 hours ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    02/16/27 - 02/19/27

    Round trip

    Economy

    from
    $593Fare subject to changes
    Updated: 2 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 Chicago to Cabo San Lucas

    Looking for lower fares on your trip from Chicago to Cabo San Lucas? 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 Chicago to Cabo San Lucas