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Popular Chicago to Puerto Rico flight itineraries
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*Fares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Modifying this information may result in a different fare. Additional bag and optional fees for products and services may apply.
Find more Chicago to Puerto Rico deals
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From | To | Fare type | Travel dates | Price |
|---|---|---|---|---|
| Chicago (ORD) | San Juan (SJU) | Round trip I Economy | 25/10/2025 - 01/11/2025 | from $377Fare subject to changes Updated: 13 hours ago |
| Chicago (CHI) | San Juan (SJU) | Round trip I Economy | 15/10/2025 - 20/10/2025 | from $377Fare subject to changes Updated: 18 hours ago |
*Fares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Some fares listed may include one or more connections that are Basic Economy, which class is subject to additional terms and conditions. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Additional baggage fees and charges for optional products and services may apply.
Related flights.
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Explore American Airlines's Top-Pick Destinations
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From | To | Fare type | Travel dates | Price |
|---|---|---|---|---|
| Chicago (ORD) | San Juan (SJU) | Round trip I Economy | 09/09/2025 - 23/09/2025 | from $307Fare subject to changes Updated: 17 hours ago |
| Chicago (CHI) | San Juan (SJU) | Round trip I Economy | 13/05/2025 - 20/05/2025 | from $372Fare subject to changes Updated: 23 hours ago |
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From | To | Fare type | Travel dates | Price | Booking |
|---|---|---|---|---|---|
| Chicago (ORD) | London (LHR) | Round trip I Premium Economy | 01/10/2025 - 22/10/2025 | from $1,535Fare subject to changes Updated: 16 hours ago | |
| Chicago (ORD) | Athens (ATH) | Round trip I Premium Economy | 21/04/2025 - 30/04/2025 | from $1,938Fare subject to changes Updated: 15 hours ago | |
| Chicago (ORD) | Rome (FCO) | Round trip I Premium Economy | 20/10/2025 - 06/11/2025 | from $1,443Fare subject to changes Updated: 15 hours ago | |
| Chicago (ORD) | Madrid (MAD) | Round trip I Premium Economy | 19/09/2025 - 28/09/2025 | from $1,407Fare subject to changes Updated: 13 hours ago | |
| Chicago (ORD) | Paris (CDG) | Round trip I Premium Economy | 10/09/2025 - 24/09/2025 | from $1,566Fare subject to changes Updated: 13 hours ago | |
| Chicago (ORD) | Tokyo (TYO) | Round trip I Premium Economy | 27/09/2025 - 11/10/2025 | from $3,412Fare subject to changes Updated: 12 hours ago | |
| Chicago (ORD) | Honolulu (HNL) | Round trip I Premium Economy | 11/09/2025 - 17/09/2025 | from $1,751Fare subject to changes Updated: 17 hours ago | |
| Chicago (ORD) | Barcelona (BCN) | Round trip I Premium Economy | 17/09/2025 - 30/09/2025 | from $1,995Fare subject to changes Updated: 11 hours ago | |
| Chicago (ORD) | Dublin (DUB) | Round trip I Premium Economy | 18/08/2025 - 25/08/2025 | from $1,749Fare subject to changes Updated: 13 hours ago | |
| Chicago (ORD) | London (LON) | Round trip I Premium Economy | 24/09/2025 - 08/10/2025 | from $1,636Fare subject to changes Updated: 15 hours ago | |
| Chicago (ORD) | Tokyo (HND) | Round trip I Premium Economy | 04/07/2025 - 19/07/2025 | from $4,316Fare subject to changes Updated: 10 hours ago | |
| Chicago (ORD) | Naples (NAP) | Round trip I Premium Economy | 19/08/2025 - 29/08/2025 | from $1,855Fare subject to changes Updated: 13 hours ago | |
| Chicago (ORD) | Maui (OGG) | Round trip I Premium Economy | 05/08/2025 - 09/08/2025 | from $1,681Fare subject to changes Updated: 10 hours ago | |
| Chicago (ORD) | Lisbon (LIS) | Round trip I Premium Economy | 04/08/2025 - 18/09/2025 | from $1,688Fare subject to changes Updated: 11 hours ago | |
| Chicago (CHI) | London (LON) | Round trip I Premium Economy | 12/08/2025 - 26/08/2025 | from $1,687Fare subject to changes Updated: 9 hours ago | |
| Chicago (ORD) | Sydney (SYD) | Round trip I Premium Economy | 10/09/2025 - 24/09/2025 | from $3,810Fare subject to changes Updated: 10 hours ago | |
| Chicago (ORD) | Kauai (LIH) | Round trip I Premium Economy | 01/10/2025 - 08/10/2025 | from $2,978Fare subject to changes Updated: 17 hours ago | |
| Chicago (ORD) | Amsterdam (AMS) | Round trip I Premium Economy | 15/10/2025 - 24/10/2025 | from $2,077Fare subject to changes Updated: 17 hours ago | |
| Chicago (CHI) | Paris (PAR) | Round trip I Premium Economy | 12/05/2025 - 19/05/2025 | from $1,757Fare subject to changes Updated: 12 hours ago | |
| Chicago (CHI) | Rome (ROM) | Round trip I Premium Economy | 15/08/2025 - 23/08/2025 | from $2,096Fare subject to changes Updated: 13 hours ago |
Interlinking Feature (TC#4) #%#Origin.Country#%#
- Interlinking Feature (TC#4) the United States
- Interlinking Feature (TC#4) England
- Interlinking Feature (TC#4) Australia
- Interlinking Feature (TC#4) Mexico
- Interlinking Feature (TC#4) Japan
- Interlinking Feature (TC#4) Spain
- Interlinking Feature (TC#4) Cuba
- Interlinking Feature (TC#4) Italy
- Interlinking Feature (TC#4) the Dominican Republic
- Interlinking Feature (TC#4) Argentina
- Interlinking Feature (TC#4) Puerto Rico
- Interlinking Feature (TC#4) France
- Interlinking Feature (TC#4) Aruba
- Interlinking Feature (TC#4) Brazil
- Interlinking Feature (TC#4) China
- Interlinking Feature (TC#4) Peru
- Interlinking Feature (TC#4) Ireland