American Airlines flights from San Diego to Chicago

Recent searches for flights from San Diego to Chicago

Sep 2026
From$277*
Updated: 11 hours ago
Round tripIEconomy
Oct 2026
From$277*
Updated: 21 hours ago
Round tripIEconomy
Nov 2026
From$277*
Updated: 2 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $277
cmp-daily-histogram-bars-legend-max-price-aria-label $445
Displaying fares for September-2026
  • SAN–ORD, 09/07/26 – 09/09/26: From $405
    07

    Mo

    SEP

  • SAN–ORD, 09/08/26 – 09/15/26: From $375
    08

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  • SAN–ORD, 09/09/26 – 09/16/26: From $375
    09

    We

  • SAN–ORD, 09/10/26 – 09/17/26: From $435
    10

    Th

  • SAN–ORD, 09/11/26 – 09/18/26: From $435
    11

    Fr

  • SAN–ORD, 09/12/26 – 09/19/26: From $375
    12

    Sa

  • SAN–ORD, 09/13/26 – 09/18/26: From $435
    13

    Su

  • SAN–ORD, 09/14/26 – 09/21/26: From $435
    14

    Mo

  • SAN–ORD, 09/15/26 – 09/22/26: From $375
    15

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  • SAN–ORD, 09/16/26 – 09/23/26: From $375
    16

    We

  • SAN–ORD, 09/17/26 – 09/24/26: From $445
    17

    Th

  • SAN–ORD, 09/18/26 – 09/25/26: From $435
    18

    Fr

  • SAN–ORD, 09/19/26 – 09/26/26: From $375
    19

    Sa

  • SAN–ORD, 09/20/26 – 09/26/26: From $405
    20

    Su

  • SAN–ORD, 09/21/26 – 09/28/26: From $356
    21

    Mo

  • SAN–ORD, 09/22/26 – 09/29/26: From $326
    22

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  • SAN–ORD, 09/23/26 – 09/30/26: From $326
    23

    We

  • SAN–ORD, 09/24/26 – 10/01/26: From $356
    24

    Th

  • SAN–ORD, 09/25/26 – 10/02/26: From $368
    25

    Fr

  • SAN–ORD, 09/26/26 – 10/03/26: From $326
    26

    Sa

  • SAN–ORD, 09/27/26 – 10/04/26: From $397
    27

    Su

  • SAN–ORD, 09/28/26 – 10/05/26: From $277
    28

    Mo

  • SAN–ORD, 09/29/26 – 10/06/26: From $277
    29

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  • SAN–ORD, 09/30/26 – 10/07/26: From $277
    30

    We

  • SAN–ORD, 10/01/26 – 10/08/26: From $277
    01

    Th

    OCT

  • SAN–ORD, 10/02/26 – 10/09/26: From $301
    02

    Fr

  • SAN–ORD, 10/03/26 – 10/10/26: From $277
    03

    Sa

  • SAN–ORD, 10/04/26 – 10/07/26: From $337
    04

    Su

  • SAN–ORD: cmp-view-offers-disclaimer. Find Offers
    05

    Mo

  • SAN–ORD: cmp-view-offers-disclaimer. Find Offers
    06

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    • range$277-$445

    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)
    10/07/26 - 10/14/26

    Round trip

    Economy

    from
    $277Fare subject to changes
    Updated: 21 hours ago

    San Diego (SAN)to

    Chicago (ORD)
    10/12/26 - 10/19/26

    Round trip

    Economy

    from
    $277Fare subject to changes
    Updated: 2 hours ago

    San Diego (SAN)to

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

    Round trip

    Economy

    from
    $277Fare subject to changes
    Updated: 2 hours ago

    San Diego (SAN)to

    Chicago (ORD)
    10/24/26 - 10/31/26

    Round trip

    Economy

    from
    $277Fare subject to changes
    Updated: 2 hours ago

    San Diego (SAN)to

    Chicago (ORD)
    12/01/26 - 12/08/26

    Round trip

    Economy

    from
    $277Fare subject to changes
    Updated: 2 hours ago

    San Diego (SAN)to

    Chicago (ORD)
    11/02/26 - 11/09/26

    Round trip

    Economy

    from
    $277Fare subject to changes
    Updated: 2 hours ago

    San Diego (SAN)to

    Chicago (ORD)
    11/03/26 - 11/10/26

    Round trip

    Economy

    from
    $277Fare subject to changes
    Updated: 2 hours ago

    San Diego (SAN)to

    Chicago (ORD)
    11/09/26 - 11/16/26

    Round trip

    Economy

    from
    $277Fare 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 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

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    • 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.
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    Discover how Main Cabin Extra can enhance your trip.

    American Airlines flights from San Diego to Chicago