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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
I
Economy		01/20/26 - 01/27/26

from

$258Fare subject to changes

Updated: 16 hours ago

Chicago (CHI)San Juan (SJU)Round trip
I
Economy		01/20/26 - 01/27/26

from

$258Fare subject to changes

Updated: 8 hours ago

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From
To
Fare type
Travel dates
Price
Booking
Chicago (ORD)Tokyo (HND)Round trip
I
Premium Economy		03/01/26 - 03/10/26

from

$3,388Fare subject to changes

Updated: 10 hours ago

Chicago (ORD)Tokyo (TYO)Round trip
I
Premium Economy		04/10/26 - 04/27/26

from

$4,333Fare subject to changes

Updated: 11 hours ago

Chicago (ORD)London (LHR)Round trip
I
Premium Economy		02/11/26 - 02/22/26

from

$1,651Fare subject to changes

Updated: 1 hour ago

Chicago (ORD)Madrid (MAD)Round trip
I
Premium Economy		03/01/26 - 03/10/26

from

$1,277Fare subject to changes

Updated: 10 hours ago

Chicago (ORD)Honolulu (HNL)Round trip
I
Premium Economy		02/10/26 - 02/16/26

from

$1,338Fare subject to changes

Updated: 15 hours ago

Chicago (ORD)Rome (FCO)Round trip
I
Premium Economy		03/24/26 - 04/01/26

from

$1,425Fare subject to changes

Updated: 8 hours ago

Chicago (ORD)Dublin (DUB)Round trip
I
Premium Economy		05/06/26 - 05/13/26

from

$1,500Fare subject to changes

Updated: 8 hours ago

Chicago (ORD)Paris (CDG)Round trip
I
Premium Economy		12/02/25 - 12/09/25

from

$1,439Fare subject to changes

Updated: 15 hours ago

Chicago (ORD)Sydney (SYD)Round trip
I
Premium Economy		12/02/25 - 12/09/25

from

$3,163Fare subject to changes

Updated: 12 hours ago

Chicago (ORD)Barcelona (BCN)Round trip
I
Premium Economy		02/18/26 - 02/25/26

from

$1,433Fare subject to changes

Updated: 11 hours ago

Chicago (ORD)London (LON)Round trip
I
Premium Economy		01/04/26 - 02/14/26

from

$1,658Fare subject to changes

Updated: 12 hours ago

Chicago (ORD)Athens (ATH)Round trip
I
Premium Economy		01/18/26 - 01/24/26

from

$1,514Fare subject to changes

Updated: 9 hours ago

Chicago (ORD)Maui (OGG)Round trip
I
Premium Economy		11/27/25 - 12/03/25

from

$1,585Fare subject to changes

Updated: 10 hours ago

Chicago (ORD)Tokyo (NRT)Round trip
I
Premium Economy		03/23/26 - 04/08/26

from

$4,253Fare subject to changes

Updated: 15 hours ago

Chicago (ORD)Lisbon (LIS)Round trip
I
Premium Economy		01/29/26 - 02/26/26

from

$1,537Fare subject to changes

Updated: 14 hours ago

Chicago (ORD)Auckland (AKL)Round trip
I
Premium Economy		01/31/26 - 02/14/26

from

$5,146Fare subject to changes

Updated: 17 hours ago

Chicago (ORD)Dubai (DXB)Round trip
I
Premium Economy		12/30/25 - 01/15/26

from

$2,503Fare subject to changes

Updated: 16 hours ago

Chicago (ORD)Kauai (LIH)Round trip
I
Premium Economy		03/01/26 - 03/04/26

from

$2,528Fare subject to changes

Updated: 11 hours ago

Chicago (ORD)Mumbai (BOM)Round trip
I
Premium Economy		11/25/25 - 12/31/25

from

$4,111Fare subject to changes

Updated: 16 hours ago

Chicago (ORD)Delhi (DEL)Round trip
I
Premium Economy		04/11/26 - 04/18/26

from

$1,995Fare subject to changes

Updated: 13 hours ago

Interlinking Feature (TC#4) #%#Origin.Country#%#

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Dallas (DFW)to

New York (LGA)
12/20/25 - 01/03/26

Round trip

Economy

from
$327Fare subject to changes
Updated: 1 hour ago

New York (JFK)to

London (LHR)
12/04/25 - 12/11/25

Round trip

Economy

from
$492Fare subject to changes
Updated: 4 minutes ago

Dallas (DFW)to

Miami (MIA)
12/16/25 - 12/23/25

Round trip

Economy

from
$207Fare subject to changes
Updated: 8 minutes ago

Dallas (DFW)to

London (LHR)
11/18/25 - 11/25/25

Round trip

Economy

from
$731Fare subject to changes
Updated: 47 minutes ago

Los Angeles (LAX)to

Tokyo (HND)
01/21/26 - 01/28/26

Round trip

Economy

from
$670Fare subject to changes
Updated: 11 minutes ago

Los Angeles (LAX)to

New York (JFK)
01/11/26 - 01/18/26

Round trip

Economy

from
$216Fare subject to changes
Updated: 18 minutes ago

Dallas (DFW)to

Tokyo (HND)
02/01/26 - 02/08/26

Round trip

Economy

from
$1,289Fare subject to changes
Updated: 13 minutes ago

Dallas (DFW)to

Los Angeles (LAX)
01/07/26 - 01/14/26

Round trip

Economy

from
$151Fare subject to changes
Updated: 1 minute ago

Dallas (DFW)to

Las Vegas (LAS)
12/09/25 - 12/16/25

Round trip

Economy

from
$131Fare subject to changes
Updated: 16 minutes ago

Philadelphia (PHL)to

Orlando (MCO)
12/06/25 - 12/13/25

Round trip

Economy

from
$159Fare subject to changes
Updated: 1 hour ago

Chicago (ORD)to

Miami (MIA)
12/24/25 - 01/03/26

Round trip

Economy

from
$542Fare subject to changes
Updated: 5 minutes ago

Miami (MIA)to

Tokyo (HND)
02/01/26 - 02/08/26

Round trip

Economy

from
$1,034Fare subject to changes
Updated: 22 minutes ago

Philadelphia (PHL)to

Tokyo (HND)
01/30/26 - 02/06/26

Round trip

Economy

from
$1,034Fare subject to changes
Updated: 8 minutes ago

Chicago (ORD)to

Tokyo (HND)
01/13/26 - 01/20/26

Round trip

Economy

from
$1,134Fare subject to changes
Updated: 22 minutes ago

Charlotte (CLT)to

Tokyo (HND)
01/30/26 - 02/06/26

Round trip

Economy

from
$1,034Fare subject to changes
Updated: 1 hour ago

Dallas (DFW)to

Orlando (MCO)
12/14/25 - 12/17/25

Round trip

Economy

from
$159Fare subject to changes
Updated: 1 hour ago

New York (JFK)to

Los Angeles (LAX)
01/11/26 - 01/18/26

Round trip

Economy

from
$216Fare subject to changes
Updated: 3 minutes ago

Dallas (DFW)to

Amarillo (AMA)
01/13/26 - 01/20/26

Round trip

Economy

from
$107Fare subject to changes
Updated: 7 minutes ago

Los Angeles (LAX)to

Miami (MIA)
12/09/25 - 12/23/25

Round trip

Economy

from
$295Fare subject to changes
Updated: 1 hour ago

Dallas (DFW)to

Cancun (CUN)
01/20/26 - 01/27/26

Round trip

Economy

from
$292Fare subject to changes
Updated: 9 minutes ago

QA FE Asset in CP VGA-2437

QA FE Interlinking Proximity VGA-2471

QA FE BUG-2112 Popularity

QA FE BUG-2112 Prepro__ Miami

QA FE BUG-2112 Prepro__ Tokyo

QA FE BUG-2112 Prepro__ New York

QA FE BUG-2112 Prepro__ Los Angeles

QA FE BUG-2112 Prepro__ Las Vegas

QA FE BUG-2112 Prepro__ Orlando

QA FE BUG-2112 Prepro__ Amarillo

QA FE BUG-2112 Prepro__ Phoenix

QA FE BUG-2112 Prepro__ Cancun

QA FE BUG-2112 Prepro__ Sydney

QA FE BUG-2112 Prepro__ Melbourne

QA FE BUG-2112 Prepro__ Madrid

QA FE BUG-2112 Prepro__ Fort Lauderdale

QA FE BUG-2112 Prepro__ Chicago

QA FE BUG-2112 Prepro__ Boston

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