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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		01/26/26 - 01/30/26

from

$216Fare subject to changes

Updated: 18 hours ago

Chicago (CHI)San Juan (SJU)Round trip
I
Economy		03/26/26 - 03/31/26

from

$391Fare subject to changes

Updated: 14 hours ago

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From
To
Fare type
Travel dates
Price
Booking
Chicago (ORD)Los Angeles (LAX)Round trip
I
Premium Economy		03/20/26 - 03/27/26

from

$2,148Fare subject to changes

Updated: 1 hour ago

Chicago (ORD)Tokyo (TYO)Round trip
I
Premium Economy		02/19/26 - 03/03/26

from

$3,011Fare subject to changes

Updated: 17 hours ago

Chicago (ORD)London (LHR)Round trip
I
Premium Economy		01/13/26 - 01/20/26

from

$1,609Fare subject to changes

Updated: 7 hours ago

Chicago (ORD)Tokyo (HND)Round trip
I
Premium Economy		04/25/26 - 05/08/26

from

$3,050Fare subject to changes

Updated: 13 hours ago

Chicago (ORD)Rome (FCO)Round trip
I
Premium Economy		01/27/26 - 02/04/26

from

$1,446Fare subject to changes

Updated: 6 hours ago

Chicago (ORD)Honolulu (HNL)Round trip
I
Premium Economy		01/18/26 - 01/24/26

from

$1,229Fare subject to changes

Updated: 10 hours ago

Chicago (ORD)Dublin (DUB)Round trip
I
Premium Economy		03/30/26 - 04/09/26

from

$1,491Fare subject to changes

Updated: 12 hours ago

Chicago (ORD)Barcelona (BCN)Round trip
I
Premium Economy		02/01/26 - 02/09/26

from

$1,466Fare subject to changes

Updated: 4 hours ago

Chicago (ORD)Madrid (MAD)Round trip
I
Premium Economy		04/07/26 - 04/22/26

from

$1,420Fare subject to changes

Updated: 9 hours ago

Chicago (ORD)Paris (CDG)Round trip
I
Premium Economy		02/22/26 - 03/03/26

from

$1,467Fare subject to changes

Updated: 7 hours ago

Chicago (ORD)Athens (ATH)Round trip
I
Premium Economy		03/17/26 - 03/31/26

from

$1,487Fare subject to changes

Updated: 12 hours ago

Chicago (ORD)Tokyo (NRT)Round trip
I
Premium Economy		05/17/26 - 05/25/26

from

$3,524Fare subject to changes

Updated: 14 hours ago

Chicago (ORD)London (LON)Round trip
I
Premium Economy		02/25/26 - 03/02/26

from

$1,659Fare subject to changes

Updated: 8 hours ago

Chicago (ORD)Maui (OGG)Round trip
I
Premium Economy		01/18/26 - 01/24/26

from

$1,640Fare subject to changes

Updated: 8 hours ago

Chicago (ORD)Naples (NAP)Round trip
I
Premium Economy		05/15/26 - 05/22/26

from

$2,007Fare subject to changes

Updated: 6 hours ago

Chicago (ORD)Lisbon (LIS)Round trip
I
Premium Economy		01/15/26 - 01/20/26

from

$1,488Fare subject to changes

Updated: 10 hours ago

Chicago (ORD)Shanghai (PVG)Round trip
I
Premium Economy		03/16/26 - 03/22/26

from

$2,068Fare subject to changes

Updated: 16 hours ago

Chicago (ORD)Sydney (SYD)Round trip
I
Premium Economy		02/08/26 - 02/15/26

from

$7,907Fare subject to changes

Updated: 7 hours ago

Chicago (ORD)Mumbai (BOM)Round trip
I
Premium Economy		02/03/26 - 02/08/26

from

$3,018Fare subject to changes

Updated: 12 hours ago

Chicago (ORD)Kona (KOA)Round trip
I
Premium Economy		03/17/26 - 03/31/26

from

$1,784Fare subject to changes

Updated: 13 hours ago

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Dallas (DFW)to

New York (LGA)
01/23/26 - 01/24/26

Round trip

Economy

from
$213Fare subject to changes
Updated: 1 hour ago

New York (JFK)to

London (LHR)
03/08/26 - 03/16/26

Round trip

Economy

from
$495Fare subject to changes
Updated: 2 hours ago

Phoenix (PHX)to

Miami (MIA)
01/31/26 - 02/07/26

Round trip

Economy

from
$147Fare subject to changes
Updated: 1 hour ago

Dallas (DFW)to

Los Angeles (LAX)
01/10/26 - 01/11/26

Round trip

Economy

from
$409Fare subject to changes
Updated: 45 minutes ago

Dallas (DFW)to

London (LHR)
01/06/26 - 01/09/26

Round trip

Economy

from
$2,520Fare subject to changes
Updated: 1 hour ago

Dallas (DFW)to

Miami (MIA)
02/12/26 - 02/19/26

Round trip

Economy

from
$229Fare subject to changes
Updated: 5 minutes ago

Los Angeles (LAX)to

New York (JFK)
02/09/26 - 02/15/26

Round trip

Economy

from
$272Fare subject to changes
Updated: 10 minutes ago

Phoenix (PHX)to

Flagstaff (FLG)
03/06/26 - 03/10/26

Round trip

Economy

from
$362Fare subject to changes
Updated: 30 minutes ago

Dallas (DFW)to

Las Vegas (LAS)
01/18/26 - 01/25/26

Round trip

Economy

from
$414Fare subject to changes
Updated: 2 hours ago

Los Angeles (LAX)to

Tokyo (TYO)
03/24/26 - 04/08/26

Round trip

Economy

from
$1,361Fare subject to changes
Updated: 20 minutes ago

Dallas (DFW)to

Cancun (CUN)
01/05/26 - 01/08/26

Round trip

Economy

from
$673Fare subject to changes
Updated: 1 hour ago

Chicago (ORD)to

Miami (MIA)
03/15/26 - 03/20/26

Round trip

Economy

from
$383Fare subject to changes
Updated: 2 hours ago

Dallas (DFW)to

Orlando (MCO)
01/02/26 - 01/06/26

Round trip

Economy

from
$402Fare subject to changes
Updated: 23 minutes ago

Los Angeles (LAX)to

Tokyo (HND)
02/16/26 - 02/26/26

Round trip

Economy

from
$620Fare subject to changes
Updated: 2 hours ago

Washington, D.C. (DCA)to

Miami (MIA)
01/15/26 - 01/19/26

Round trip

Economy

from
$348Fare subject to changes
Updated: 2 hours ago

Chicago (ORD)to

Phoenix (PHX)
02/08/26 - 02/11/26

Round trip

Economy

from
$197Fare subject to changes
Updated: 2 hours ago

Philadelphia (PHL)to

Miami (MIA)
01/13/26 - 01/19/26

Round trip

Economy

from
$337Fare subject to changes
Updated: 11 minutes ago

Dallas (DFW)to

Tokyo (TYO)
01/14/26 - 01/23/26

Round trip

Economy

from
$849Fare subject to changes
Updated: 50 minutes ago

New York (LGA)to

Miami (MIA)
12/30/25 - 01/02/26

Round trip

Economy

from
$714Fare subject to changes
Updated: 2 hours ago

Los Angeles (LAX)to

Melbourne (MEL)
02/12/26 - 02/19/26

Round trip

Economy

from
$1,037Fare subject to changes
Updated: 1 minutes ago

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QA FE BUG-2112 Prepro__ London

QA FE BUG-2112 Prepro__ Miami

QA FE BUG-2112 Prepro__ Los Angeles

QA FE BUG-2112 Prepro__ Orlando

QA FE BUG-2112 Prepro__ Flagstaff

QA FE BUG-2112 Prepro__ Las Vegas

QA FE BUG-2112 Prepro__ Tokyo

QA FE BUG-2112 Prepro__ Cancun

QA FE BUG-2112 Prepro__ Fort Lauderdale

QA FE BUG-2112 Prepro__ Phoenix

QA FE BUG-2112 Prepro__ Amarillo

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QA FE BUG-2112 Prepro__ Madrid

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  • Dallas (DFW)to

    London (LHR)
    01/06/26 - 01/09/26
    from
    $2,520Fare subject to changes
    Updated: 1 hour ago
    Round trip
    Economy

    Dallas (DFW)to

    Miami (MIA)
    02/12/26 - 02/19/26
    from
    $229Fare subject to changes
    Updated: 5 minutes ago
    Round trip
    Economy

    Los Angeles (LAX)to

    New York (JFK)
    02/09/26 - 02/15/26
    from
    $272Fare subject to changes
    Updated: 10 minutes ago
    Round trip
    Economy

    Phoenix (PHX)to

    Flagstaff (FLG)
    03/06/26 - 03/10/26
    from
    $362Fare subject to changes
    Updated: 30 minutes ago
    Round trip
    Economy

  • Dallas (DFW)to

    Las Vegas (LAS)
    01/18/26 - 01/25/26
    from
    $414Fare subject to changes
    Updated: 2 hours ago
    Round trip
    Economy

    Los Angeles (LAX)to

    Tokyo (TYO)
    03/24/26 - 04/08/26
    from
    $1,361Fare subject to changes
    Updated: 20 minutes ago
    Round trip
    Economy

    Dallas (DFW)to

    Cancun (CUN)
    01/05/26 - 01/08/26
    from
    $673Fare subject to changes
    Updated: 1 hour ago
    Round trip
    Economy

    Chicago (ORD)to

    Miami (MIA)
    03/15/26 - 03/20/26
    from
    $383Fare subject to changes
    Updated: 2 hours ago
    Round trip
    Economy

  • Dallas (DFW)to

    Orlando (MCO)
    01/02/26 - 01/06/26
    from
    $402Fare subject to changes
    Updated: 23 minutes ago
    Round trip
    Economy

    Los Angeles (LAX)to

    Tokyo (HND)
    02/16/26 - 02/26/26
    from
    $620Fare subject to changes
    Updated: 2 hours ago
    Round trip
    Economy

    Washington, D.C. (DCA)to

    Miami (MIA)
    01/15/26 - 01/19/26
    from
    $348Fare subject to changes
    Updated: 2 hours ago
    Round trip
    Economy

    Chicago (ORD)to

    Phoenix (PHX)
    02/08/26 - 02/11/26
    from
    $197Fare subject to changes
    Updated: 2 hours ago
    Round trip
    Economy

  • Philadelphia (PHL)to

    Miami (MIA)
    01/13/26 - 01/19/26
    from
    $337Fare subject to changes
    Updated: 11 minutes ago
    Round trip
    Economy

    Dallas (DFW)to

    Tokyo (TYO)
    01/14/26 - 01/23/26
    from
    $849Fare subject to changes
    Updated: 50 minutes ago
    Round trip
    Economy

    New York (LGA)to

    Miami (MIA)
    12/30/25 - 01/02/26
    from
    $714Fare subject to changes
    Updated: 2 hours ago
    Round trip
    Economy

    Los Angeles (LAX)to

    Melbourne (MEL)
    02/12/26 - 02/19/26
    from
    $1,037Fare subject to changes
    Updated: 1 minutes ago
    Round trip
    Economy