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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.

American Airlines flights from Chicago to Cayman Islands

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From
To
Fare type
Travel dates
Price
Chicago (ORD)Grand Cayman (GCM)Round trip
I
Economy		05/05/26 - 05/12/26

from

$499Fare subject to changes

Updated: 21 hours ago

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From
To
Fare type
Travel dates
Price
Booking
Chicago (ORD)Tokyo (TYO)Round trip
I
Premium Economy		08/20/26 - 09/02/26

from

$3,457Fare subject to changes

Updated: 2 hours ago

Chicago (ORD)Los Angeles (LAX)Round trip
I
Premium Economy		03/12/26 - 03/16/26

from

$1,955Fare subject to changes

Updated: 10 hours ago

Chicago (ORD)San Francisco (SFO)Round trip
I
Premium Economy		08/05/26 - 08/09/26

from

$1,256Fare subject to changes

Updated: 14 hours ago

Chicago (ORD)London (LHR)Round trip
I
Premium Economy		03/24/26 - 03/31/26

from

$1,657Fare subject to changes

Updated: 4 hours ago

Chicago (ORD)Tokyo (HND)Round trip
I
Premium Economy		03/04/26 - 03/11/26

from

$3,475Fare subject to changes

Updated: 1 hour ago

Chicago (ORD)Rome (FCO)Round trip
I
Premium Economy		03/23/26 - 04/01/26

from

$1,432Fare subject to changes

Updated: 3 hours ago

Chicago (ORD)Athens (ATH)Round trip
I
Premium Economy		03/04/26 - 03/11/26

from

$1,671Fare subject to changes

Updated: 8 hours ago

Chicago (ORD)Honolulu (HNL)Round trip
I
Premium Economy		03/22/26 - 03/31/26

from

$1,656Fare subject to changes

Updated: 11 hours ago

Chicago (ORD)Madrid (MAD)Round trip
I
Premium Economy		04/21/26 - 04/29/26

from

$1,262Fare subject to changes

Updated: 7 hours ago

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

from

$1,499Fare subject to changes

Updated: 7 hours ago

Chicago (ORD)Dublin (DUB)Round trip
I
Premium Economy		08/23/26 - 09/02/26

from

$1,361Fare subject to changes

Updated: 8 hours ago

Chicago (ORD)Barcelona (BCN)Round trip
I
Premium Economy		08/09/26 - 08/19/26

from

$1,570Fare subject to changes

Updated: 9 hours ago

Chicago (ORD)Tokyo (NRT)Round trip
I
Premium Economy		07/02/26 - 07/09/26

from

$2,546Fare subject to changes

Updated: 6 hours ago

Chicago (CHI)Los Angeles (LAX)Round trip
I
Premium Economy		02/28/26 - 03/01/26

from

$1,384Fare subject to changes

Updated: 13 hours ago

Chicago (ORD)Maui (OGG)Round trip
I
Premium Economy		08/12/26 - 08/20/26

from

$2,055Fare subject to changes

Updated: 8 hours ago

Chicago (ORD)London (LON)Round trip
I
Premium Economy		03/11/26 - 03/17/26

from

$1,631Fare subject to changes

Updated: 6 hours ago

Chicago (ORD)Naples (NAP)Round trip
I
Premium Economy		08/09/26 - 08/24/26

from

$1,581Fare subject to changes

Updated: 13 hours ago

Chicago (ORD)Lisbon (LIS)Round trip
I
Premium Economy		04/20/26 - 05/10/26

from

$1,531Fare subject to changes

Updated: 11 hours ago

Chicago (ORD)Kauai (LIH)Round trip
I
Premium Economy		08/12/26 - 08/19/26

from

$1,901Fare subject to changes

Updated: 10 hours ago

Chicago (CHI)San Francisco (SFO)Round trip
I
Premium Economy		06/20/26 - 06/25/26

from

$1,289Fare subject to changes

Updated: 12 hours ago

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

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Dallas (DFW)to

London (LHR)
05/06/26 - 05/13/26

Round trip

Economy

from
$835Fare subject to changes
Updated: 1 hour ago

Dallas (DFW)to

New York (LGA)
05/16/26 - 05/20/26

Round trip

Economy

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

Dallas (DFW)to

Los Angeles (LAX)
04/21/26 - 04/28/26

Round trip

Economy

from
$249Fare subject to changes
Updated: 2 hours ago

Los Angeles (LAX)to

Melbourne (MEL)
05/20/26 - 06/10/26

Round trip

Economy

from
$1,231Fare subject to changes
Updated: 2 hours ago

Los Angeles (LAX)to

New York (JFK)
05/09/26 - 05/12/26

Round trip

Economy

from
$264Fare subject to changes
Updated: 44 minutes ago

Dallas (DFW)to

Miami (MIA)
04/07/26 - 04/22/26

Round trip

Economy

from
$219Fare subject to changes
Updated: 27 minutes ago

Miami (MIA)to

New York (NYC)
03/12/26 - 03/18/26

Round trip

Economy

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

Phoenix (PHX)to

Flagstaff (FLG)
04/10/26 - 04/12/26

Round trip

Economy

from
$406Fare subject to changes
Updated: 1 hour ago

Philadelphia (PHL)to

Orlando (MCO)
05/02/26 - 05/06/26

Round trip

Economy

from
$244Fare subject to changes
Updated: 1 hour ago

Dallas (DFW)to

Las Vegas (LAS)
04/10/26 - 04/14/26

Round trip

Economy

from
$284Fare subject to changes
Updated: 1 hour ago

New York (JFK)to

London (LHR)
03/29/26 - 04/13/26

Round trip

Economy

from
$512Fare subject to changes
Updated: 2 hours ago

Dallas (DFW)to

Orlando (MCO)
04/05/26 - 04/11/26

Round trip

Economy

from
$299Fare subject to changes
Updated: 2 hours ago

Philadelphia (PHL)to

Tampa (TPA)
04/16/26 - 04/20/26

Round trip

Economy

from
$290Fare subject to changes
Updated: 3 hours ago

Los Angeles (LAX)to

Tokyo (HND)
04/06/26 - 04/22/26

Round trip

Economy

from
$859Fare subject to changes
Updated: 1 hour ago

Chicago (ORD)to

Phoenix (PHX)
04/30/26 - 05/04/26

Round trip

Economy

from
$175Fare subject to changes
Updated: 2 hours ago

Dallas (DFW)to

Chicago (ORD)
05/02/26 - 05/06/26

Round trip

Economy

from
$143Fare subject to changes
Updated: 2 hours ago

Philadelphia (PHL)to

Fort Lauderdale (FLL)
04/11/26 - 04/21/26

Round trip

Economy

from
$99Fare subject to changes
Updated: 2 hours ago

Miami (MIA)to

New York (LGA)
03/17/26 - 03/18/26

Round trip

Economy

from
$147Fare subject to changes
Updated: 2 hours ago

Phoenix (PHX)to

Miami (MIA)
04/27/26 - 05/13/26

Round trip

Economy

from
$237Fare subject to changes
Updated: 25 minutes ago

Los Angeles (LAX)to

Tokyo (TYO)
03/04/26 - 03/11/26

Round trip

Economy

from
$860Fare subject to changes
Updated: 2 hours ago

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QA FE BUG-2112 Prepro__ Miami

QA FE BUG-2112 Prepro__ Los Angeles

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__ Austin

QA FE BUG-2112 Prepro__ Melbourne

QA FE BUG-2112 Prepro__ Flagstaff

QA FE BUG-2112 Prepro__ Orlando

QA FE BUG-2112 Prepro__ Las Vegas

QA FE BUG-2112 Prepro__ Tampa

QA FE BUG-2112 Prepro__ Tokyo

QA FE BUG-2112 Prepro__ Phoenix

QA FE BUG-2112 Prepro__ Chicago

QA FE BUG-2112 Prepro__ Fort Lauderdale

QA FE VGA-2704 Round trip on Economy

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  • Los Angeles (LAX)to

    New York (JFK)
    05/09/26 - 05/12/26
    from
    $264Fare subject to changes
    Updated: 44 minutes ago
    Round trip
    Economy

    Dallas (DFW)to

    Miami (MIA)
    04/07/26 - 04/22/26
    from
    $219Fare subject to changes
    Updated: 27 minutes ago
    Round trip
    Economy

    Miami (MIA)to

    New York (NYC)
    04/24/26 - 04/26/26
    from
    $147Fare subject to changes
    Updated: 2 hours ago
    Round trip
    Economy

    Phoenix (PHX)to

    Flagstaff (FLG)
    04/10/26 - 04/12/26
    from
    $406Fare subject to changes
    Updated: 1 hour ago
    Round trip
    Economy

  • Philadelphia (PHL)to

    Orlando (MCO)
    04/30/26 - 05/05/26
    from
    $244Fare subject to changes
    Updated: 2 hours ago
    Round trip
    Economy

    Dallas (DFW)to

    Las Vegas (LAS)
    04/10/26 - 04/14/26
    from
    $284Fare subject to changes
    Updated: 1 hour ago
    Round trip
    Economy

    New York (JFK)to

    London (LHR)
    05/13/26 - 05/20/26
    from
    $512Fare subject to changes
    Updated: 1 hour ago
    Round trip
    Economy

    Dallas (DFW)to

    Orlando (MCO)
    04/05/26 - 04/11/26
    from
    $299Fare subject to changes
    Updated: 2 hours ago
    Round trip
    Economy

  • Philadelphia (PHL)to

    Tampa (TPA)
    04/16/26 - 04/20/26
    from
    $290Fare subject to changes
    Updated: 3 hours ago
    Round trip
    Economy

    Los Angeles (LAX)to

    Tokyo (HND)
    04/06/26 - 04/22/26
    from
    $859Fare subject to changes
    Updated: 1 hour ago
    Round trip
    Economy

    Chicago (ORD)to

    Phoenix (PHX)
    05/01/26 - 05/04/26
    from
    $175Fare subject to changes
    Updated: 2 hours ago
    Round trip
    Economy

    Dallas (DFW)to

    Chicago (ORD)
    05/02/26 - 05/06/26
    from
    $143Fare subject to changes
    Updated: 2 hours ago
    Round trip
    Economy

  • Philadelphia (PHL)to

    Fort Lauderdale (FLL)
    04/11/26 - 04/21/26
    from
    $99Fare subject to changes
    Updated: 2 hours ago
    Round trip
    Economy

    Miami (MIA)to

    New York (LGA)
    03/17/26 - 03/18/26
    from
    $147Fare subject to changes
    Updated: 2 hours ago
    Round trip
    Economy

    Phoenix (PHX)to

    Miami (MIA)
    04/27/26 - 05/13/26
    from
    $237Fare subject to changes
    Updated: 25 minutes ago
    Round trip
    Economy

    Los Angeles (LAX)to

    Tokyo (TYO)
    03/04/26 - 03/11/26
    from
    $860Fare subject to changes
    Updated: 2 hours ago
    Round trip
    Economy