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)

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Oct 2026
No results for this month.
Nov 2026
from$99*
Last seen: 15 hours ago
One-way/Economy
Dec 2026
from$101*
Last seen: 19 hours ago
One-way/Economy
cmp-daily-histogram-bars-legend-min-price-aria-label $99
cmp-daily-histogram-bars-legend-max-price-aria-label $212
Displaying fares for October-2026
  • ORD–SJU: cmp-view-offers-disclaimer. Find Offers
    31

    Sat

    OCT

  • ORD–SJU: cmp-view-offers-disclaimer. Find Offers
    01

    Sun

  • ORD–SJU, Nov 2, 2026: from $148
    02

    Mon

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

    Tue

  • ORD–SJU, Nov 4, 2026: from $148
    04

    Wed

  • ORD–SJU, Nov 5, 2026: from $148
    05

    Thu

  • ORD–SJU, Nov 6, 2026: from $207
    06

    Fri

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

    Sat

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

    Sun

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

    Mon

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

    Tue

  • ORD–SJU: cmp-view-offers-disclaimer. Find Offers
    11

    Wed

  • ORD–SJU: cmp-view-offers-disclaimer. Find Offers
    12

    Thu

  • ORD–SJU, Nov 13, 2026: from $137
    13

    Fri

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

    Sat

  • ORD–SJU, Nov 15, 2026: from $136
    15

    Sun

  • ORD–SJU, Nov 16, 2026: from $136
    16

    Mon

  • ORD–SJU: cmp-view-offers-disclaimer. Find Offers
    17

    Tue

  • ORD–SJU: cmp-view-offers-disclaimer. Find Offers
    18

    Wed

  • ORD–SJU, Nov 19, 2026: from $173
    19

    Thu

  • ORD–SJU, Nov 20, 2026: from $205
    20

    Fri

  • ORD–SJU, Nov 21, 2026: from $200
    21

    Sat

  • ORD–SJU: cmp-view-offers-disclaimer. Find Offers
    22

    Sun

  • ORD–SJU, Nov 23, 2026: from $121
    23

    Mon

  • ORD–SJU, Nov 24, 2026: from $202
    24

    Tue

  • ORD–SJU, Nov 25, 2026: from $200
    25

    Wed

  • ORD–SJU, Nov 26, 2026: from $99
    26

    Thu

  • ORD–SJU, Nov 27, 2026: from $115
    27

    Fri

  • ORD–SJU, Nov 28, 2026: from $212
    28

    Sat

  • ORD–SJU, Nov 29, 2026: from $209
    29

    Sun

  • ORD–SJU: cmp-view-offers-disclaimer. Find Offers
    30

    Mon

    • Range$99-$212

    *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 Mar 16, 2027

    From

    $83

    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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