American Airlines flights from Chicago to Cabo San Lucas

Recent searches for flights from Chicago to Cabo San Lucas

Sep 2026
From$654*
Updated: 12 hours ago
Round tripIEconomy
Oct 2026
From$550*
Updated: 12 hours ago
Round tripIEconomy
Nov 2026
From$546*
Updated: 3 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $555
cmp-daily-histogram-bars-legend-max-price-aria-label $881
Displaying fares for September-2026
  • ORD–SJD: cmp-view-offers-disclaimer. Find Offers
    10

    Th

    SEP

  • ORD–SJD, 09/11/26 – 09/18/26: From $808
    11

    Fr

  • ORD–SJD, 09/12/26 – 09/19/26: From $768
    12

    Sa

  • ORD–SJD, 09/13/26 – 09/20/26: From $861
    13

    Su

  • ORD–SJD, 09/14/26 – 09/21/26: From $881
    14

    Mo

  • ORD–SJD, 09/15/26 – 09/22/26: From $763
    15

    Tu

  • ORD–SJD, 09/16/26 – 09/23/26: From $768
    16

    We

  • ORD–SJD, 09/17/26 – 09/24/26: From $808
    17

    Th

  • ORD–SJD, 09/18/26 – 09/25/26: From $808
    18

    Fr

  • ORD–SJD, 09/19/26 – 09/26/26: From $768
    19

    Sa

  • ORD–SJD, 09/20/26 – 09/27/26: From $844
    20

    Su

  • ORD–SJD, 09/21/26 – 09/28/26: From $806
    21

    Mo

  • ORD–SJD, 09/22/26 – 09/29/26: From $763
    22

    Tu

  • ORD–SJD, 09/23/26 – 09/29/26: From $760
    23

    We

  • ORD–SJD, 09/24/26 – 10/01/26: From $725
    24

    Th

  • ORD–SJD, 09/25/26 – 10/02/26: From $725
    25

    Fr

  • ORD–SJD, 09/26/26 – 10/03/26: From $727
    26

    Sa

  • ORD–SJD, 09/27/26 – 10/04/26: From $801
    27

    Su

  • ORD–SJD, 09/28/26 – 10/05/26: From $717
    28

    Mo

  • ORD–SJD, 09/29/26 – 10/06/26: From $654
    29

    Tu

  • ORD–SJD, 09/30/26 – 10/07/26: From $707
    30

    We

  • ORD–SJD, 10/01/26 – 10/08/26: From $687
    01

    Th

    OCT

  • ORD–SJD, 10/02/26 – 10/09/26: From $618
    02

    Fr

  • ORD–SJD, 10/03/26 – 10/10/26: From $618
    03

    Sa

  • ORD–SJD, 10/04/26 – 10/08/26: From $555
    04

    Su

  • ORD–SJD, 10/05/26 – 10/12/26: From $682
    05

    Mo

  • ORD–SJD, 10/06/26 – 10/13/26: From $560
    06

    Tu

  • ORD–SJD, 10/07/26 – 10/14/26: From $654
    07

    We

  • ORD–SJD, 10/08/26 – 10/15/26: From $843
    08

    Th

  • ORD–SJD, 10/09/26 – 10/16/26: From $804
    09

    Fr

    • range$555-$881

    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)
    11/15/26 - 11/20/26

    Round trip

    Economy

    from
    $546Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    01/31/27 - 02/05/27

    Round trip

    Economy

    from
    $546Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    11/10/26 - 11/13/26

    Round trip

    Economy

    from
    $546Fare subject to changes
    Updated: 3 hours ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    12/06/26 - 12/09/26

    Round trip

    Economy

    from
    $546Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    01/11/27 - 01/15/27

    Round trip

    Economy

    from
    $546Fare subject to changes
    Updated: 22 hours ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    02/01/27 - 02/05/27

    Round trip

    Economy

    from
    $546Fare subject to changes
    Updated: 23 hours ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    01/12/27 - 01/15/27

    Round trip

    Economy

    from
    $546Fare subject to changes
    Updated: 17 hours ago

    Chicago (ORD)to

    Cabo San Lucas (SJD)
    11/03/26 - 11/06/26

    Round trip

    Economy

    from
    $546Fare subject to changes
    Updated: 22 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

    Citi / AAdvantage credit card offer.

    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