Flights from San Juan, PR to Chicago, IL

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Best Deals on Flights From San Juan, PR (SJU) to Chicago, IL (ORD)

Try alternate month or interact with individual days below in order to find offers.
Jul 2026
No results for this month.
Aug 2026
from$87*
Last seen: 2 mins ago
One-way/Economy
Sep 2026
from$58*
Last seen: 7 hours ago
One-way/Economy
cmp-daily-histogram-bars-legend-min-price-aria-label $87
cmp-daily-histogram-bars-legend-max-price-aria-label $267
Displaying fares for July-2026
  • SJU–ORD: cmp-view-offers-disclaimer. Find Offers
    30

    Thu

    JUL

  • SJU–ORD: cmp-view-offers-disclaimer. Find Offers
    31

    Fri

  • SJU–ORD, Aug 1, 2026: from $267
    01

    Sat

    AUG

  • SJU–ORD, Aug 2, 2026: from $267
    02

    Sun

  • SJU–ORD, Aug 3, 2026: from $234
    03

    Mon

  • SJU–ORD, Aug 4, 2026: from $208
    04

    Tue

  • SJU–ORD, Aug 5, 2026: from $163
    05

    Wed

  • SJU–ORD, Aug 6, 2026: from $177
    06

    Thu

  • SJU–ORD, Aug 7, 2026: from $187
    07

    Fri

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

    Sat

  • SJU–ORD, Aug 9, 2026: from $247
    09

    Sun

  • SJU–ORD, Aug 10, 2026: from $247
    10

    Mon

  • SJU–ORD, Aug 11, 2026: from $215
    11

    Tue

  • SJU–ORD, Aug 12, 2026: from $163
    12

    Wed

  • SJU–ORD, Aug 13, 2026: from $158
    13

    Thu

  • SJU–ORD, Aug 14, 2026: from $208
    14

    Fri

  • SJU–ORD: cmp-view-offers-disclaimer. Find Offers
    15

    Sat

  • SJU–ORD, Aug 16, 2026: from $208
    16

    Sun

  • SJU–ORD, Aug 17, 2026: from $206
    17

    Mon

  • SJU–ORD, Aug 18, 2026: from $152
    18

    Tue

  • SJU–ORD, Aug 19, 2026: from $125
    19

    Wed

  • SJU–ORD: cmp-view-offers-disclaimer. Find Offers
    20

    Thu

  • SJU–ORD: cmp-view-offers-disclaimer. Find Offers
    21

    Fri

  • SJU–ORD, Aug 22, 2026: from $135
    22

    Sat

  • SJU–ORD, Aug 23, 2026: from $118
    23

    Sun

  • SJU–ORD, Aug 24, 2026: from $123
    24

    Mon

  • SJU–ORD, Aug 25, 2026: from $129
    25

    Tue

  • SJU–ORD, Aug 26, 2026: from $87
    26

    Wed

  • SJU–ORD, Aug 27, 2026: from $89
    27

    Thu

  • SJU–ORD, Aug 28, 2026: from $159
    28

    Fri

  • SJU–ORD, Aug 29, 2026: from $108
    29

    Sat

    • Range$87-$267

    *Prices found by others in the previous 48 hours for round-trip flights. Prices shown may also require membership in our travel club, Discount Den.

    Flights Deals from San Juan, PR to Chicago, IL on Frontier

    $
    Flights Deals from San Juan, PR to Chicago, IL on Frontier
    From
    To
    San Juan, PR (SJU)Chicago, IL (ORD)One-way
    /
    Discount Den Basic Fare    		Departing Nov 18, 2026

    From

    $65

    Last seen: 19 hours ago

    *Prices found by others in the previous 48 hours for one-way flights. Prices shown may also require membership in our travel club, Discount Den®.

    San Juan, PR Chicago, IL

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