$70 Cheap flight deals from Chicago (CHI) to Puerto Rico Island (SJU)
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This Weekend's Flight Deals from Chicago to Puerto Rico Island
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $70 One Way, $187 Round Trip from Chicago to Puerto Rico Island
Prices starting at $187 for return flights and $70 for one-way flights to Puerto Rico Island were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Puerto Rico Island economy flight packages
San Agustin Apartments
Sep 25 - Sep 28
Chicago (CHI) to San Juan (SJU)
Reviewed on Jul 25, 2025
Puerto Rico Island packages with premium economy flights
Hotel Puerto Valdes
Sep 13 - Sep 20
Chicago (CHI) to San Juan (SJU)
Reviewed on Sep 3, 2024
Las Casitas Village at El Conquistador
Sep 13 - Sep 20
Chicago (CHI) to San Juan (SJU)
Reviewed on Mar 14, 2025
Puerto Rico Island first class flight packages
Hotel Puerto Valdes
Sep 13 - Sep 21
Chicago (CHI) to San Juan (SJU)
San Juan (SJU) to Chicago (CHI)
Reviewed on Sep 3, 2024
Aire de O:live
Sep 13 - Sep 19
Chicago (CHI) to San Juan (SJU)
Reviewed on Apr 9, 2025
OLV Fifty Five - Adults Only
Sep 13 - Sep 19
Chicago (CHI) to San Juan (SJU)
Reviewed on Aug 7, 2023
More About Flying To Puerto Rico Island from Chicago
Route Information for Flights from Chicago to Puerto Rico Island
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | SJU |
Distance | 2073 mi |
Direct Flight Airlines | American Airlines, Air Canada, Alaska Airlines, Air New Zealand, United Airlines, Spirit Airlines |
Earliest Flight Arrival | 6:05PM UTC |
Latest Flight Arrival | 3:54AM UTC |
Chicago to Puerto Rico Island
It has never been easier to find cheap Chicago to Puerto Rico Island flights. Orbitz has some of the best deals around to save you more money on your flight, hotel, and vacation package for the trip you have been waiting for.
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Get the Best Deals on Chicago to Puerto Rico Island Flights
Finding great deals on flights from Chicago to Puerto Rico Island is a snap with Orbitz. With our guaranteed low prices, you don’t have to worry if you are getting the best prices on air tickets, hotels, and cruises. And with all that money you saved, you can enjoy your Puerto Rico Island vacation even more.
Pile Up Miles With Discount Air Tickets
Not only can you find great bargains on Chicago to Puerto Rico Island flights, but you can rack up frequent flyer miles on the flights too. Enter your frequent flyer number on qualified flights when booking for Orbitz to see the miles pile up in your account.
Flight Alerts Keep You Informed
Stay on top of the latest updates for flights from Chicago to Puerto Rico Island. We send you free email and mobile alerts to keep you informed about delays to Chicago to Puerto Rico Island flights.
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.