American Airlines flights from San Juan to Chicago

Recent searches for flights from San Juan to Chicago

Aug 2026
FromUSD427*
Updated: 4 hours ago
Round tripIEconomy
Sep 2026
FromUSD226*
Updated: 4 hours ago
Round tripIEconomy
Oct 2026
FromUSD222*
Updated: 5 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label USD226
cmp-daily-histogram-bars-legend-max-price-aria-label USD553
Displaying fares for August-2026
  • SJU–CHI, 08/31/26 – 09/07/26: From USD427
    31

    Mo

    AUG

  • SJU–ORD, 09/01/26 – 09/08/26: From USD327
    01

    Tu

  • SJU–CHI, 09/02/26 – 09/09/26: From USD292
    02

    We

  • SJU–CHI, 09/03/26 – 09/10/26: From USD287
    03

    Th

  • SJU–ORD, 09/04/26 – 09/08/26: From USD291
    04

    Fr

  • SJU–CHI, 09/05/26 – 09/12/26: From USD287
    05

    Sa

  • SJU–ORD, 09/06/26 – 09/13/26: From USD266
    06

    Su

  • SJU–CHI, 09/07/26 – 09/14/26: From USD553
    07

    Mo

  • SJU–CHI, 09/08/26 – 09/15/26: From USD431
    08

    Tu

  • SJU–CHI, 09/09/26 – 09/16/26: From USD271
    09

    We

  • SJU–CHI, 09/10/26 – 09/17/26: From USD266
    10

    Th

  • SJU–CHI, 09/11/26 – 09/18/26: From USD266
    11

    Fr

  • SJU–ORD, 09/12/26 – 09/19/26: From USD266
    12

    Sa

  • SJU–ORD, 09/13/26 – 09/20/26: From USD366
    13

    Su

  • SJU–CHI, 09/14/26 – 09/21/26: From USD366
    14

    Mo

  • SJU–ORD, 09/15/26 – 09/22/26: From USD366
    15

    Tu

  • SJU–CHI, 09/16/26 – 09/23/26: From USD251
    16

    We

  • SJU–ORD, 09/17/26 – 09/24/26: From USD376
    17

    Th

  • SJU–CHI, 09/18/26 – 09/25/26: From USD246
    18

    Fr

  • SJU–CHI, 09/19/26 – 09/26/26: From USD384
    19

    Sa

  • SJU–CHI, 09/20/26 – 09/27/26: From USD356
    20

    Su

  • SJU–CHI, 09/21/26 – 09/28/26: From USD356
    21

    Mo

  • SJU–CHI, 09/22/26 – 09/29/26: From USD356
    22

    Tu

  • SJU–CHI, 09/23/26 – 09/30/26: From USD361
    23

    We

  • SJU–ORD, 09/24/26 – 10/01/26: From USD226
    24

    Th

  • SJU–CHI, 09/25/26 – 10/02/26: From USD226
    25

    Fr

  • SJU–CHI, 09/26/26 – 10/03/26: From USD226
    26

    Sa

  • SJU–CHI: cmp-view-offers-disclaimer. Find Offers
    27

    Su

  • SJU–CHI: cmp-view-offers-disclaimer. Find Offers
    28

    Mo

  • SJU–CHI: cmp-view-offers-disclaimer. Find Offers
    29

    Tu

  • SJU–CHI, 09/30/26 – 10/07/26: From USD231
    30

    We

    • rangeUSD226-USD553

    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.

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    *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.

    American Airlines flights from San Juan to Chicago

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