Chicago to San Juan in September 2026

Dated one-way fares from Chicago to San Juan in September 2026. Use the calendar to see which days are cheaper.

Lowest this month $89

Highest this month $169

Sample fare $89

Airports ORD–SJU

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September 2026 price calendar

From $89 · up to $169

Mon

Tue

Wed

Thu

Fri

Sat

Sun

6 $89 7 $129 8 $129 9 $129 10 $129 11 $129 12 $129 13 $129 14 $129 15 $129 16 $129 17 $129 18 $169 19 $118 20 $125 21 $159 22 $118

San Juan SJU

$89

Sep 06, 12:44am · 5h · 0 stops

ORD → SJU · Frontier Airlines

San Juan SJU

$118

Sep 19, 8:55am · 4h 49m · 0 stops

ORD → SJU · United Airlines

San Juan SJU

$118

Sep 22, 8:55am · 4h 49m · 0 stops

ORD → SJU · United Airlines

San Juan SJU

$125

Sep 20, 5:30am · 9h 12m · 1 stop

ORD → SJU · United Airlines

This page is only September 2026 on the Chicago to San Juan route. Open the full route if you want the next months side by side.

Prices move as seats sell. Confirm the live itinerary before you book Chicago to San Juan in September 2026.