Flights from Chicago, IL to San Juan, PR

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

Sep 2026
from$189*
Last seen: 17 hours ago
One-way/Economy
Oct 2026
from$103*
Last seen: 19 hours ago
One-way/Economy
Nov 2026
from$126*
Last seen: 43 mins ago
One-way/Economy
cmp-daily-histogram-bars-legend-min-price-aria-label $148
cmp-daily-histogram-bars-legend-max-price-aria-label $257
Displaying fares for September-2026
  • ORD–SJU: cmp-view-offers-disclaimer. Find Offers
    13

    Sun

    SEP

  • ORD–SJU: cmp-view-offers-disclaimer. Find Offers
    14

    Mon

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

    Tue

  • ORD–SJU, Sep 16, 2026: from $232
    16

    Wed

  • ORD–SJU, Sep 17, 2026: from $254
    17

    Thu

  • ORD–SJU, Sep 18, 2026: from $242
    18

    Fri

  • ORD–SJU, Sep 19, 2026: from $245
    19

    Sat

  • ORD–SJU, Sep 20, 2026: from $220
    20

    Sun

  • ORD–SJU, Sep 21, 2026: from $220
    21

    Mon

  • ORD–SJU, Sep 22, 2026: from $215
    22

    Tue

  • ORD–SJU, Sep 23, 2026: from $227
    23

    Wed

  • ORD–SJU, Sep 24, 2026: from $257
    24

    Thu

  • ORD–SJU: cmp-view-offers-disclaimer. Find Offers
    25

    Fri

  • ORD–SJU, Sep 26, 2026: from $213
    26

    Sat

  • ORD–SJU, Sep 27, 2026: from $213
    27

    Sun

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

    Mon

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

    Tue

  • ORD–SJU, Sep 30, 2026: from $189
    30

    Wed

  • ORD–SJU, Oct 1, 2026: from $208
    01

    Thu

    OCT

  • ORD–SJU, Oct 2, 2026: from $158
    02

    Fri

  • ORD–SJU, Oct 3, 2026: from $148
    03

    Sat

  • ORD–SJU: cmp-view-offers-disclaimer. Find Offers
    04

    Sun

  • ORD–SJU, Oct 5, 2026: from $162
    05

    Mon

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

    Tue

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

    Wed

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

    Thu

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

    Fri

  • ORD–SJU: cmp-view-offers-disclaimer. Find Offers
    10

    Sat

  • ORD–SJU, Oct 11, 2026: from $186
    11

    Sun

  • ORD–SJU, Oct 12, 2026: from $257
    12

    Mon

    • Range$148-$257

    *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 Chicago, IL to San Juan, PR on Frontier

    $
    Flights Deals from Chicago, IL to San Juan, PR on Frontier
    From
    To
    Chicago, IL (ORD)San Juan, PR (SJU)One-way
    /
    Discount Den Basic Fare    		Departing Jan 2, 2027

    From

    $180

    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®.

    Chicago, IL San Juan, PR

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