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Chicago, United States to San Juan, Puerto Rico for only $191 USD roundtrip

Fly from Chicago, United States to San Juan, Puerto Rico for only $191 USD roundtrip.

October 07, 2026

BOOK ON GOOGLE FLIGHTS
⚠️ Heads up: Deals typically expire within 2 to 3 days after they are sent. Prices may also increase slightly after 30 minutes, so act quickly!

Alternative Checkout Options
Book on Kiwi
Book on CheapOair
Deal Details
From:
🇺🇸 Chicago (ORD), United States
To:
🇵🇷 San Juan (SJU), Puerto Rico
Travel Between:
Class:
Price:
$191 Save $95
Normal Price:
$286
Airlines:
Expiration Details:
These fares will last no more than 1-2 days and typically go up within 30 minutes.
How To Book
Note: To find the cheapest available fares, click the 'Pick a date' button. You'll be redirected to Kiwi.com with the flight dates pre-filled and the cabin class set to Economy by default. You can change it to your preferred class at any time.
Travel Dates
From Date To Date
November 10, 2026 November 13, 2026
Options
Baggage allowance:
Intermediate stops:
Business Class:
No
Round-trip:
Yes
Non-stop:
No

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