American Airlines flights from San Juan to Chicago

Recent searches for flights from San Juan to Chicago

Aug 2026
FromUSD247*
Updated: 21 hours ago
Round tripIEconomy
Sep 2026
FromUSD307*
Updated: 6 hours ago
Round tripIEconomy
Oct 2026
FromUSD457*
Updated: 6 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label USD247
cmp-daily-histogram-bars-legend-max-price-aria-label USD594
Displaying fares for August-2026
  • SJU–CHI: cmp-view-offers-disclaimer. Find Offers
    10

    Mo

    AUG

  • SJU–CHI, 08/11/26 – 08/18/26: From USD493
    11

    Tu

  • SJU–ORD, 08/12/26 – 08/19/26: From USD493
    12

    We

  • SJU–ORD, 08/13/26 – 08/16/26: From USD377
    13

    Th

  • SJU–CHI, 08/14/26 – 08/21/26: From USD377
    14

    Fr

  • SJU–CHI, 08/15/26 – 08/22/26: From USD417
    15

    Sa

  • SJU–CHI, 08/16/26 – 08/23/26: From USD594
    16

    Su

  • SJU–CHI, 08/17/26 – 08/24/26: From USD322
    17

    Mo

  • SJU–CHI, 08/18/26 – 08/25/26: From USD322
    18

    Tu

  • SJU–CHI, 08/19/26 – 08/26/26: From USD282
    19

    We

  • SJU–ORD, 08/20/26 – 08/27/26: From USD362
    20

    Th

  • SJU–CHI, 08/21/26 – 08/28/26: From USD322
    21

    Fr

  • SJU–CHI, 08/22/26 – 08/29/26: From USD392
    22

    Sa

  • SJU–ORD, 08/23/26 – 08/30/26: From USD362
    23

    Su

  • SJU–CHI, 08/24/26 – 08/31/26: From USD322
    24

    Mo

  • SJU–ORD, 08/25/26 – 09/01/26: From USD287
    25

    Tu

  • SJU–CHI, 08/26/26 – 09/02/26: From USD292
    26

    We

  • SJU–ORD, 08/27/26 – 08/30/26: From USD247
    27

    Th

  • SJU–ORD, 08/28/26 – 08/31/26: From USD247
    28

    Fr

  • SJU–ORD, 08/29/26 – 09/05/26: From USD347
    29

    Sa

  • SJU–ORD, 08/30/26 – 09/06/26: From USD287
    30

    Su

  • SJU–CHI, 08/31/26 – 09/07/26: From USD341
    31

    Mo

  • SJU–ORD, 09/01/26 – 09/08/26: From USD307
    01

    Tu

    SEP

  • SJU–ORD, 09/02/26 – 09/09/26: From USD397
    02

    We

  • SJU–CHI, 09/03/26 – 09/10/26: From USD417
    03

    Th

  • SJU–ORD, 09/04/26 – 09/11/26: From USD417
    04

    Fr

  • SJU–ORD, 09/05/26 – 09/12/26: From USD417
    05

    Sa

  • SJU–CHI, 09/06/26 – 09/13/26: From USD396
    06

    Su

  • SJU–CHI: cmp-view-offers-disclaimer. Find Offers
    07

    Mo

  • SJU–CHI: cmp-view-offers-disclaimer. Find Offers
    08

    Tu

  • SJU–CHI: cmp-view-offers-disclaimer. Find Offers
    09

    We

    • rangeUSD247-USD594

    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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