American Airlines flights from Chicago to Cabo San Lucas

Recent searches for flights from Chicago to Cabo San Lucas

Aug 2026
From$753*
Updated: 3 hours ago
Round tripIEconomy
Sep 2026
From$633*
Updated: 8 hours ago
Round tripIEconomy
Oct 2026
From$583*
Updated: 3 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $643
cmp-daily-histogram-bars-legend-max-price-aria-label $2.1K
Displaying fares for August-2026
  • CHI–SJD: cmp-view-offers-disclaimer. Find Offers
    24

    Mo

    AUG

  • ORD–SJD, 08/25/26 – 09/01/26: From $900
    25

    Tu

  • ORD–SJD, 08/26/26 – 09/02/26: From $905
    26

    We

  • CHI–SJD, 08/27/26 – 09/03/26: From $900
    27

    Th

  • CHI–SJD, 08/28/26 – 09/04/26: From $900
    28

    Fr

  • CHI–SJD, 08/29/26 – 09/03/26: From $753
    29

    Sa

  • CHI–SJD, 08/30/26 – 09/06/26: From $950
    30

    Su

  • ORD–SJD, 08/31/26 – 09/07/26: From $2,108
    31

    Mo

  • ORD–SJD, 09/01/26 – 09/08/26: From $2,038
    01

    Tu

    SEP

  • ORD–SJD, 09/02/26 – 09/09/26: From $1,093
    02

    We

  • CHI–SJD, 09/03/26 – 09/10/26: From $898
    03

    Th

  • CHI–SJD, 09/04/26 – 09/11/26: From $858
    04

    Fr

  • ORD–SJD, 09/05/26 – 09/12/26: From $830
    05

    Sa

  • ORD–SJD, 09/06/26 – 09/10/26: From $788
    06

    Su

  • CHI–SJD, 09/07/26 – 09/14/26: From $778
    07

    Mo

  • CHI–SJD, 09/08/26 – 09/15/26: From $703
    08

    Tu

  • ORD–SJD, 09/09/26 – 09/16/26: From $708
    09

    We

  • CHI–SJD, 09/10/26 – 09/17/26: From $745
    10

    Th

  • CHI–SJD, 09/11/26 – 09/18/26: From $745
    11

    Fr

  • ORD–SJD, 09/12/26 – 09/19/26: From $728
    12

    Sa

  • ORD–SJD, 09/13/26 – 09/20/26: From $1,083
    13

    Su

  • CHI–SJD, 09/14/26 – 09/21/26: From $803
    14

    Mo

  • CHI–SJD, 09/15/26 – 09/22/26: From $643
    15

    Tu

  • CHI–SJD, 09/16/26 – 09/23/26: From $693
    16

    We

  • ORD–SJD, 09/17/26 – 09/24/26: From $668
    17

    Th

  • ORD–SJD, 09/18/26 – 09/25/26: From $668
    18

    Fr

  • CHI–SJD, 09/19/26 – 09/26/26: From $668
    19

    Sa

  • ORD–SJD, 09/20/26 – 09/27/26: From $723
    20

    Su

  • ORD–SJD, 09/21/26 – 09/28/26: From $668
    21

    Mo

  • CHI–SJD, 09/22/26 – 09/29/26: From $643
    22

    Tu

  • ORD–SJD, 09/23/26 – 09/30/26: From $708
    23

    We

    • range$643-$2,108

    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)
    11/08/26 - 11/13/26

    Round trip

    Economy

    from
    $579Fare subject to changes
    Updated: 23 hours ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    01/10/27 - 01/16/27

    Round trip

    Economy

    from
    $557Fare subject to changes
    Updated: 1 hour ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    11/14/26 - 11/21/26

    Round trip

    Economy

    from
    $561Fare subject to changes
    Updated: 1 hour ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    02/03/27 - 02/07/27

    Round trip

    Economy

    from
    $567Fare subject to changes
    Updated: 48 minutes ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    10/17/26 - 10/21/26

    Round trip

    Economy

    from
    $583Fare subject to changes
    Updated: 3 hours ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    02/10/27 - 02/17/27

    Round trip

    Economy

    from
    $584Fare subject to changes
    Updated: 9 hours ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    11/11/26 - 11/18/26

    Round trip

    Economy

    from
    $588Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    10/16/26 - 10/19/26

    Round trip

    Economy

    from
    $597Fare subject to changes
    Updated: 27 minutes 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