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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		06/01/26 - 06/12/26

from

$237Fare subject to changes

Updated: 3 hours ago

Chicago (CHI)San Juan (SJU)Round trip
I
Economy		06/02/26 - 06/14/26

from

$237Fare subject to changes

Updated: 23 hours ago

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From
To
Fare type
Travel dates
Price
Booking
Chicago (ORD)Los Angeles (LAX)Round trip
I
Premium Economy		08/26/26 - 09/01/26

from

$1,876Fare subject to changes

Updated: 4 hours ago

Chicago (ORD)San Francisco (SFO)Round trip
I
Premium Economy		08/07/26 - 08/08/26

from

$2,137Fare subject to changes

Updated: 15 hours ago

Chicago (ORD)Tokyo (TYO)Round trip
I
Premium Economy		04/17/26 - 05/07/26

from

$3,390Fare subject to changes

Updated: 1 hour ago

Chicago (ORD)London (LHR)Round trip
I
Premium Economy		04/13/26 - 04/23/26

from

$1,672Fare subject to changes

Updated: 17 hours ago

Chicago (ORD)Rome (FCO)Round trip
I
Premium Economy		02/24/26 - 03/03/26

from

$1,469Fare subject to changes

Updated: 4 hours ago

Chicago (ORD)Athens (ATH)Round trip
I
Premium Economy		03/03/26 - 03/10/26

from

$1,526Fare subject to changes

Updated: 29 minutes ago

Chicago (ORD)Dublin (DUB)Round trip
I
Premium Economy		04/20/26 - 04/28/26

from

$1,397Fare subject to changes

Updated: 16 hours ago

Chicago (ORD)Madrid (MAD)Round trip
I
Premium Economy		03/10/26 - 03/17/26

from

$1,247Fare subject to changes

Updated: 55 minutes ago

Chicago (ORD)Honolulu (HNL)Round trip
I
Premium Economy		02/24/26 - 03/03/26

from

$1,627Fare subject to changes

Updated: 7 minutes ago

Chicago (ORD)Barcelona (BCN)Round trip
I
Premium Economy		04/08/26 - 04/14/26

from

$1,570Fare subject to changes

Updated: 3 hours ago

Chicago (ORD)Paris (CDG)Round trip
I
Premium Economy		04/23/26 - 05/03/26

from

$2,054Fare subject to changes

Updated: 2 hours ago

Chicago (ORD)Tokyo (HND)Round trip
I
Premium Economy		08/12/26 - 08/28/26

from

$3,410Fare subject to changes

Updated: 1 hour ago

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

from

$2,649Fare subject to changes

Updated: 23 minutes ago

Chicago (CHI)Los Angeles (LAX)Round trip
I
Premium Economy		03/14/26 - 03/16/26

from

$2,144Fare subject to changes

Updated: 1 hour ago

Chicago (ORD)Maui (OGG)Round trip
I
Premium Economy		03/08/26 - 03/15/26

from

$2,227Fare subject to changes

Updated: 2 hours ago

Chicago (ORD)Lisbon (LIS)Round trip
I
Premium Economy		04/08/26 - 04/20/26

from

$1,620Fare subject to changes

Updated: 7 hours ago

Chicago (ORD)London (LON)Round trip
I
Premium Economy		08/23/26 - 09/03/26

from

$1,672Fare subject to changes

Updated: 13 hours ago

Chicago (ORD)Venice (VCE)Round trip
I
Premium Economy		04/03/26 - 04/10/26

from

$5,181Fare subject to changes

Updated: 3 hours ago

Chicago (CHI)London (LON)Round trip
I
Premium Economy		04/29/26 - 05/04/26

from

$1,748Fare subject to changes

Updated: 15 hours ago

Chicago (ORD)Delhi (DEL)Round trip
I
Premium Economy		05/28/26 - 06/14/26

from

$2,153Fare subject to changes

Updated: 13 hours ago

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Dallas (DFW)to

London (LHR)
05/13/26 - 05/20/26

Round trip

Economy

from
$830Fare subject to changes
Updated: 1 hour ago

Dallas (DFW)to

New York (LGA)
05/02/26 - 05/06/26

Round trip

Economy

from
$179Fare subject to changes
Updated: 2 hours ago

Los Angeles (LAX)to

Melbourne (MEL)
03/17/26 - 03/22/26

Round trip

Economy

from
$1,053Fare subject to changes
Updated: 2 hours ago

Dallas (DFW)to

Los Angeles (LAX)
05/16/26 - 05/20/26

Round trip

Economy

from
$253Fare subject to changes
Updated: 2 hours ago

Dallas (DFW)to

Miami (MIA)
03/03/26 - 03/04/26

Round trip

Economy

from
$279Fare subject to changes
Updated: 1 hour ago

Los Angeles (LAX)to

New York (JFK)
04/22/26 - 04/25/26

Round trip

Economy

from
$272Fare subject to changes
Updated: 2 hours ago

Philadelphia (PHL)to

Orlando (MCO)
05/06/26 - 05/12/26

Round trip

Economy

from
$209Fare subject to changes
Updated: 2 hours ago

Dallas (DFW)to

Las Vegas (LAS)
04/07/26 - 04/08/26

Round trip

Economy

from
$234Fare subject to changes
Updated: 1 hour ago

New York (JFK)to

London (LHR)
02/23/26 - 02/28/26

Round trip

Economy

from
$507Fare subject to changes
Updated: 14 minutes ago

Dallas (DFW)to

Orlando (MCO)
04/22/26 - 04/29/26

Round trip

Economy

from
$209Fare subject to changes
Updated: 2 hours ago

Los Angeles (LAX)to

Denver (DEN)
04/28/26 - 04/29/26

Round trip

Economy

from
$158Fare subject to changes
Updated: 5 minutes ago

Phoenix (PHX)to

Miami (MIA)
03/03/26 - 03/05/26

Round trip

Economy

from
$207Fare subject to changes
Updated: 2 hours ago

Dallas (DFW)to

Amarillo (AMA)
03/25/26 - 03/26/26

Round trip

Economy

from
$244Fare subject to changes
Updated: 34 minutes ago

Chicago (ORD)to

Las Vegas (LAS)
05/06/26 - 05/08/26

Round trip

Economy

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

Philadelphia (PHL)to

Fort Lauderdale (FLL)
05/02/26 - 05/09/26

Round trip

Economy

from
$107Fare subject to changes
Updated: 8 minutes ago

Philadelphia (PHL)to

Tampa (TPA)
04/08/26 - 04/14/26

Round trip

Economy

from
$213Fare subject to changes
Updated: 14 minutes ago

Miami (MIA)to

Madrid (MAD)
04/22/26 - 04/29/26

Round trip

Economy

from
$424Fare subject to changes
Updated: 2 hours ago

Dallas (DFW)to

Cancun (CUN)
04/05/26 - 04/09/26

Round trip

Economy

from
$457Fare subject to changes
Updated: 1 hour ago

Chicago (ORD)to

Phoenix (PHX)
04/18/26 - 04/21/26

Round trip

Economy

from
$197Fare subject to changes
Updated: 1 hour ago

Philadelphia (PHL)to

Fort Myers (RSW)
05/13/26 - 05/20/26

Round trip

Economy

from
$179Fare subject to changes
Updated: 1 hour ago

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QA FE BUG-2112 Prepro__ Los Angeles

QA FE BUG-2112 Prepro__ Miami

QA FE BUG-2112 Prepro__ Washington, D.C.

QA FE BUG-2112 Prepro__ London

QA FE BUG-2112 Prepro__ New York

QA FE BUG-2112 Prepro__ Melbourne

QA FE BUG-2112 Prepro__ Flagstaff

QA FE BUG-2112 Prepro__ Austin

QA FE BUG-2112 Prepro__ Orlando

QA FE BUG-2112 Prepro__ Las Vegas

QA FE BUG-2112 Prepro__ Denver

QA FE BUG-2112 Prepro__ Amarillo

QA FE BUG-2112 Prepro__ Fort Lauderdale

QA FE BUG-2112 Prepro__ Tampa

QA FE BUG-2112 Prepro__ Madrid

QA FE VGA-2704 Round trip on Economy

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  • Dallas (DFW)to

    Miami (MIA)
    03/03/26 - 03/04/26
    from
    $279Fare subject to changes
    Updated: 1 hour ago
    Round trip
    Economy

    Los Angeles (LAX)to

    New York (JFK)
    04/22/26 - 04/25/26
    from
    $272Fare subject to changes
    Updated: 2 hours ago
    Round trip
    Economy

    Philadelphia (PHL)to

    Orlando (MCO)
    05/06/26 - 05/12/26
    from
    $209Fare subject to changes
    Updated: 2 hours ago
    Round trip
    Economy

    Dallas (DFW)to

    Las Vegas (LAS)
    04/07/26 - 04/08/26
    from
    $234Fare subject to changes
    Updated: 1 hour ago
    Round trip
    Economy

  • New York (JFK)to

    London (LHR)
    02/23/26 - 02/28/26
    from
    $507Fare subject to changes
    Updated: 14 minutes ago
    Round trip
    Economy

    Dallas (DFW)to

    Orlando (MCO)
    03/24/26 - 03/31/26
    from
    $209Fare subject to changes
    Updated: 1 hour ago
    Round trip
    Economy

    Los Angeles (LAX)to

    Denver (DEN)
    04/28/26 - 04/29/26
    from
    $158Fare subject to changes
    Updated: 5 minutes ago
    Round trip
    Economy

    Phoenix (PHX)to

    Miami (MIA)
    03/03/26 - 03/11/26
    from
    $207Fare subject to changes
    Updated: 1 hour ago
    Round trip
    Economy

  • Dallas (DFW)to

    Amarillo (AMA)
    03/25/26 - 03/26/26
    from
    $244Fare subject to changes
    Updated: 34 minutes ago
    Round trip
    Economy

    Chicago (ORD)to

    Las Vegas (LAS)
    04/25/26 - 04/29/26
    from
    $197Fare subject to changes
    Updated: 2 hours ago
    Round trip
    Economy

    Philadelphia (PHL)to

    Fort Lauderdale (FLL)
    05/02/26 - 05/09/26
    from
    $107Fare subject to changes
    Updated: 8 minutes ago
    Round trip
    Economy

    Philadelphia (PHL)to

    Tampa (TPA)
    04/08/26 - 04/14/26
    from
    $213Fare subject to changes
    Updated: 14 minutes ago
    Round trip
    Economy

  • Miami (MIA)to

    Madrid (MAD)
    04/22/26 - 04/29/26
    from
    $424Fare subject to changes
    Updated: 2 hours ago
    Round trip
    Economy

    Dallas (DFW)to

    Cancun (CUN)
    03/17/26 - 03/24/26
    from
    $457Fare subject to changes
    Updated: 2 hours ago
    Round trip
    Economy

    Chicago (ORD)to

    Phoenix (PHX)
    04/18/26 - 04/21/26
    from
    $197Fare subject to changes
    Updated: 1 hour ago
    Round trip
    Economy

    Philadelphia (PHL)to

    Fort Myers (RSW)
    05/13/26 - 05/20/26
    from
    $179Fare subject to changes
    Updated: 1 hour ago
    Round trip
    Economy