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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.

American Airlines flights from Chicago to Puerto Rico

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From
To
Fare type
Travel dates
Price
Chicago (ORD)San Juan (SJU)Round trip
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Economy		09/14/25 - 09/20/25

from

$355Fare subject to changes

Updated: 21 hours ago

Chicago (CHI)San Juan (SJU)Round trip
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Economy		05/07/25 - 05/14/25

from

$377Fare subject to changes

Updated: 8 hours ago

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From
To
Fare type
Travel dates
Price
Booking
Chicago (ORD)London (LHR)Round trip
I
Premium Economy		10/11/25 - 10/24/25

from

$1,567Fare subject to changes

Updated: 9 hours ago

Chicago (ORD)Rome (FCO)Round trip
I
Premium Economy		08/25/25 - 12/13/25

from

$1,972Fare subject to changes

Updated: 2 hours ago

Chicago (ORD)Athens (ATH)Round trip
I
Premium Economy		08/02/25 - 08/20/25

from

$2,440Fare subject to changes

Updated: 16 hours ago

Chicago (ORD)Madrid (MAD)Round trip
I
Premium Economy		10/08/25 - 10/14/25

from

$1,486Fare subject to changes

Updated: 13 hours ago

Chicago (ORD)Barcelona (BCN)Round trip
I
Premium Economy		08/12/25 - 08/19/25

from

$1,705Fare subject to changes

Updated: 16 hours ago

Chicago (ORD)Paris (CDG)Round trip
I
Premium Economy		09/29/25 - 11/03/25

from

$1,573Fare subject to changes

Updated: 13 hours ago

Chicago (ORD)Dublin (DUB)Round trip
I
Premium Economy		08/18/25 - 12/23/25

from

$1,624Fare subject to changes

Updated: 16 hours ago

Chicago (ORD)Tokyo (TYO)Round trip
I
Premium Economy		09/29/25 - 10/13/25

from

$3,411Fare subject to changes

Updated: 16 hours ago

Chicago (ORD)Honolulu (HNL)Round trip
I
Premium Economy		04/29/25 - 05/09/25

from

$1,442Fare subject to changes

Updated: 9 hours ago

Chicago (ORD)Tokyo (HND)Round trip
I
Premium Economy		06/16/25 - 06/30/25

from

$6,448Fare subject to changes

Updated: 11 hours ago

Chicago (ORD)London (LON)Round trip
I
Premium Economy		10/04/25 - 10/12/25

from

$1,687Fare subject to changes

Updated: 13 hours ago

Chicago (ORD)Naples (NAP)Round trip
I
Premium Economy		09/09/25 - 09/19/25

from

$2,397Fare subject to changes

Updated: 13 hours ago

Chicago (ORD)Maui (OGG)Round trip
I
Premium Economy		09/16/25 - 09/21/25

from

$1,456Fare subject to changes

Updated: 13 hours ago

Chicago (CHI)London (LON)Round trip
I
Premium Economy		05/14/25 - 05/20/25

from

$1,749Fare subject to changes

Updated: 10 hours ago

Chicago (ORD)Lisbon (LIS)Round trip
I
Premium Economy		04/27/25 - 05/06/25

from

$1,825Fare subject to changes

Updated: 14 hours ago

Chicago (ORD)Kona (KOA)Round trip
I
Premium Economy		05/22/25 - 05/27/25

from

$2,491Fare subject to changes

Updated: 7 hours ago

Chicago (ORD)Sydney (SYD)Round trip
I
Premium Economy		08/24/25 - 09/07/25

from

$3,812Fare subject to changes

Updated: 12 hours ago

Chicago (ORD)Venice (VCE)Round trip
I
Premium Economy		10/12/25 - 10/30/25

from

$1,974Fare subject to changes

Updated: 14 hours ago

Chicago (CHI)Paris (PAR)Round trip
I
Premium Economy		10/08/25 - 10/16/25

from

$1,578Fare subject to changes

Updated: 15 hours ago

Chicago (ORD)Amsterdam (AMS)Round trip
I
Premium Economy		09/07/25 - 09/20/25

from

$2,277Fare subject to changes

Updated: 15 hours ago

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