American Airlines flights from San Diego to Chicago

Recent searches for flights from San Diego to Chicago

Aug 2026
From$346*
Updated: 9 hours ago
Round tripIEconomy
Sep 2026
From$277*
Updated: 9 hours ago
Round tripIEconomy
Oct 2026
From$277*
Updated: 9 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $277
cmp-daily-histogram-bars-legend-max-price-aria-label $415
Displaying fares for August-2026
  • SAN–CHI: cmp-view-offers-disclaimer. Find Offers
    17

    Mo

    AUG

  • SAN–CHI, 08/18/26 – 08/25/26: From $355
    18

    Tu

  • SAN–ORD, 08/19/26 – 08/26/26: From $355
    19

    We

  • SAN–ORD, 08/20/26 – 08/27/26: From $415
    20

    Th

  • SAN–CHI, 08/21/26 – 08/28/26: From $415
    21

    Fr

  • SAN–ORD, 08/22/26 – 08/29/26: From $355
    22

    Sa

  • SAN–ORD, 08/23/26 – 08/26/26: From $385
    23

    Su

  • SAN–ORD, 08/24/26 – 08/26/26: From $405
    24

    Mo

  • SAN–CHI, 08/25/26 – 09/01/26: From $355
    25

    Tu

  • SAN–CHI, 08/26/26 – 09/02/26: From $355
    26

    We

  • SAN–ORD, 08/27/26 – 09/03/26: From $415
    27

    Th

  • SAN–CHI, 08/28/26 – 09/04/26: From $415
    28

    Fr

  • SAN–ORD, 08/29/26 – 09/05/26: From $355
    29

    Sa

  • SAN–ORD, 08/30/26 – 09/12/26: From $346
    30

    Su

  • SAN–CHI, 08/31/26 – 09/07/26: From $346
    31

    Mo

  • SAN–CHI, 09/01/26 – 09/08/26: From $316
    01

    Tu

    SEP

  • SAN–ORD, 09/02/26 – 09/09/26: From $316
    02

    We

  • SAN–CHI, 09/03/26 – 09/10/26: From $346
    03

    Th

  • SAN–ORD, 09/04/26 – 09/08/26: From $346
    04

    Fr

  • SAN–CHI, 09/05/26 – 09/12/26: From $316
    05

    Sa

  • SAN–CHI, 09/06/26 – 09/13/26: From $403
    06

    Su

  • SAN–ORD, 09/07/26 – 09/14/26: From $334
    07

    Mo

  • SAN–CHI, 09/08/26 – 09/15/26: From $277
    08

    Tu

  • SAN–CHI, 09/09/26 – 09/16/26: From $277
    09

    We

  • SAN–CHI, 09/10/26 – 09/17/26: From $277
    10

    Th

  • SAN–ORD, 09/11/26 – 09/18/26: From $301
    11

    Fr

  • SAN–ORD, 09/12/26 – 09/19/26: From $277
    12

    Sa

  • SAN–ORD, 09/13/26 – 09/19/26: From $337
    13

    Su

  • SAN–CHI: cmp-view-offers-disclaimer. Find Offers
    14

    Mo

  • SAN–ORD, 09/15/26 – 09/17/26: From $277
    15

    Tu

  • SAN–ORD, 09/16/26 – 09/17/26: From $277
    16

    We

    • range$277-$415

    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 San Diego to Chicago flights

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    San Diego (SAN)to

    Chicago (ORD)
    10/17/26 - 10/24/26

    Round trip

    Economy

    from
    $277Fare subject to changes
    Updated: 9 hours ago

    San Diego (SAN)to

    Chicago (ORD)
    10/20/26 - 10/27/26

    Round trip

    Economy

    from
    $277Fare subject to changes
    Updated: 9 hours ago

    San Diego (SAN)to

    Chicago (ORD)
    10/29/26 - 11/05/26

    Round trip

    Economy

    from
    $277Fare subject to changes
    Updated: 9 hours ago

    San Diego (SAN)to

    Chicago (ORD)
    10/31/26 - 11/07/26

    Round trip

    Economy

    from
    $277Fare subject to changes
    Updated: 9 hours ago

    San Diego (SAN)to

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

    Round trip

    Economy

    from
    $277Fare subject to changes
    Updated: 9 hours ago

    San Diego (SAN)to

    Chicago (ORD)
    10/05/26 - 10/12/26

    Round trip

    Economy

    from
    $277Fare subject to changes
    Updated: 9 hours ago

    San Diego (SAN)to

    Chicago (ORD)
    10/06/26 - 10/13/26

    Round trip

    Economy

    from
    $277Fare subject to changes
    Updated: 9 hours ago

    San Diego (SAN)to

    Chicago (ORD)
    09/10/26 - 09/17/26

    Round trip

    Economy

    from
    $277Fare subject to changes
    Updated: 9 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 San Diego to Chicago

    Looking for lower fares on your trip from San Diego 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 San Diego to Chicago