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Popular Chicago to Cayman Islands 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.
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From | To | Fare type | Travel dates | Price |
|---|---|---|---|---|
| Chicago (ORD) | Grand Cayman (GCM) | Round trip I Economy | 07/02/2026 - 14/02/2026 | from $635Fare subject to changes Updated: 7 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.
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Explore American Airlines's Top-Pick Destinations
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From | To | Fare type | Travel dates | Price |
|---|---|---|---|---|
| Chicago (ORD) | Grand Cayman (GCM) | Round trip I Economy | 05/08/2025 - 12/08/2025 | from $610Fare subject to changes Updated: 8 minutes ago |
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From | To | Fare type | Travel dates | Price | Booking |
|---|---|---|---|---|---|
| Chicago (ORD) | London (LHR) | Round trip I Premium Economy | 20/10/2025 - 06/11/2025 | from $1,485Fare subject to changes Updated: 17 minutes ago | |
| Chicago (ORD) | Athens (ATH) | Round trip I Premium Economy | 20/04/2025 - 27/04/2025 | from $2,261Fare subject to changes Updated: 8 hours ago | |
| Chicago (ORD) | Rome (FCO) | Round trip I Premium Economy | 15/10/2025 - 28/10/2025 | from $1,731Fare subject to changes Updated: 1 hour ago | |
| Chicago (ORD) | Madrid (MAD) | Round trip I Premium Economy | 28/09/2025 - 07/10/2025 | from $1,288Fare subject to changes Updated: 7 hours ago | |
| Chicago (ORD) | Paris (CDG) | Round trip I Premium Economy | 18/08/2025 - 08/09/2025 | from $1,561Fare subject to changes Updated: 4 hours ago | |
| Chicago (ORD) | Tokyo (TYO) | Round trip I Premium Economy | 28/06/2025 - 06/07/2025 | from $4,940Fare subject to changes Updated: 7 hours ago | |
| Chicago (ORD) | Barcelona (BCN) | Round trip I Premium Economy | 18/08/2025 - 18/09/2025 | from $1,770Fare subject to changes Updated: 4 hours ago | |
| Chicago (ORD) | Dublin (DUB) | Round trip I Premium Economy | 14/10/2025 - 22/10/2025 | from $1,679Fare subject to changes Updated: 57 minutes ago | |
| Chicago (ORD) | Honolulu (HNL) | Round trip I Premium Economy | 12/09/2025 - 29/09/2025 | from $1,861Fare subject to changes Updated: 6 hours ago | |
| Chicago (ORD) | London (LON) | Round trip I Premium Economy | 11/08/2025 - 26/08/2025 | from $1,687Fare subject to changes Updated: 8 hours ago | |
| Chicago (ORD) | Tokyo (HND) | Round trip I Premium Economy | 06/10/2025 - 16/10/2025 | from $4,086Fare subject to changes Updated: 2 hours ago | |
| Chicago (ORD) | Naples (NAP) | Round trip I Premium Economy | 15/08/2025 - 30/08/2025 | from $1,965Fare subject to changes Updated: 2 hours ago | |
| Chicago (ORD) | Maui (OGG) | Round trip I Premium Economy | 10/09/2025 - 17/09/2025 | from $1,991Fare subject to changes Updated: 7 hours ago | |
| Chicago (CHI) | London (LON) | Round trip I Premium Economy | 16/10/2025 - 23/10/2025 | from $1,594Fare subject to changes Updated: 2 hours ago | |
| Chicago (ORD) | Lisbon (LIS) | Round trip I Premium Economy | 14/10/2025 - 31/10/2025 | from $1,756Fare subject to changes Updated: 1 hour ago | |
| Chicago (ORD) | Sydney (SYD) | Round trip I Premium Economy | 09/06/2025 - 23/06/2025 | from $3,815Fare subject to changes Updated: 10 hours ago | |
| Chicago (ORD) | Kauai (LIH) | Round trip I Premium Economy | 11/05/2025 - 16/05/2025 | from $2,115Fare subject to changes Updated: 5 minutes ago | |
| Chicago (ORD) | Bangkok (BKK) | Round trip I Premium Economy | 13/10/2025 - 19/10/2025 | from $2,996Fare subject to changes Updated: 6 hours ago | |
| Chicago (CHI) | Paris (PAR) | Round trip I Premium Economy | 30/09/2025 - 21/10/2025 | from $1,687Fare subject to changes Updated: 7 hours ago | |
| Chicago (CHI) | Rome (ROM) | Round trip I Premium Economy | 12/10/2025 - 31/10/2025 | from $1,890Fare subject to changes Updated: 8 hours ago |
Interlinking Feature (TC#4) #%#Origin.Country#%#
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