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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
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Economy		08/05/25 - 08/12/25

from

$610Fare subject to changes

Updated: 43 minutes ago

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From
To
Fare type
Travel dates
Price
Booking
Chicago (ORD)London (LHR)Round trip
I
Premium Economy		10/18/25 - 10/28/25

from

$1,544Fare subject to changes

Updated: 2 hours ago

Chicago (ORD)Rome (FCO)Round trip
I
Premium Economy		08/18/25 - 08/28/25

from

$1,876Fare subject to changes

Updated: 6 hours ago

Chicago (ORD)Athens (ATH)Round trip
I
Premium Economy		05/06/25 - 05/13/25

from

$1,923Fare subject to changes

Updated: 6 hours ago

Chicago (ORD)Madrid (MAD)Round trip
I
Premium Economy		09/17/25 - 09/24/25

from

$1,207Fare subject to changes

Updated: 13 minutes ago

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

from

$1,801Fare subject to changes

Updated: 6 hours ago

Chicago (ORD)Tokyo (TYO)Round trip
I
Premium Economy		06/14/25 - 07/02/25

from

$4,267Fare subject to changes

Updated: 5 hours ago

Chicago (ORD)Paris (CDG)Round trip
I
Premium Economy		10/12/25 - 10/21/25

from

$1,566Fare subject to changes

Updated: 3 hours ago

Chicago (ORD)Dublin (DUB)Round trip
I
Premium Economy		08/24/25 - 09/04/25

from

$1,720Fare subject to changes

Updated: 11 hours ago

Chicago (ORD)Tokyo (HND)Round trip
I
Premium Economy		09/09/25 - 09/20/25

from

$3,412Fare subject to changes

Updated: 3 hours ago

Chicago (ORD)Honolulu (HNL)Round trip
I
Premium Economy		04/20/25 - 05/03/25

from

$1,478Fare subject to changes

Updated: 4 hours ago

Chicago (ORD)Maui (OGG)Round trip
I
Premium Economy		09/11/25 - 09/15/25

from

$1,991Fare subject to changes

Updated: 7 hours ago

Chicago (ORD)Naples (NAP)Round trip
I
Premium Economy		10/16/25 - 10/30/25

from

$1,750Fare subject to changes

Updated: 7 minutes ago

Chicago (ORD)London (LON)Round trip
I
Premium Economy		10/18/25 - 10/28/25

from

$1,570Fare subject to changes

Updated: 9 hours ago

Chicago (ORD)Lisbon (LIS)Round trip
I
Premium Economy		10/02/25 - 10/16/25

from

$1,798Fare subject to changes

Updated: 4 hours ago

Chicago (ORD)Sydney (SYD)Round trip
I
Premium Economy		10/14/25 - 11/08/25

from

$3,862Fare subject to changes

Updated: 12 hours ago

Chicago (CHI)London (LON)Round trip
I
Premium Economy		08/06/25 - 08/31/25

from

$1,663Fare subject to changes

Updated: 29 minutes ago

Chicago (ORD)Kuala Lumpur (KUL)Round trip
I
Premium Economy		07/22/25 - 08/13/25

from

$4,009Fare subject to changes

Updated: 8 hours ago

Chicago (ORD)Kauai (LIH)Round trip
I
Premium Economy		10/11/25 - 10/17/25

from

$3,106Fare subject to changes

Updated: 3 hours ago

Chicago (ORD)Amsterdam (AMS)Round trip
I
Premium Economy		05/13/25 - 05/20/25

from

$1,793Fare subject to changes

Updated: 5 hours ago

Chicago (ORD)Kona (KOA)Round trip
I
Premium Economy		06/01/25 - 06/06/25

from

$2,245Fare subject to changes

Updated: 8 hours ago

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  • Dallas (DFW)to

    Miami (MIA)
    05/27/25 - 05/28/25
    from
    $218Fare subject to changes
    Updated: 2 hours ago
    Round trip
    I
    Economy

    Los Angeles (LAX)to

    New York (JFK)
    07/10/25 - 07/16/25
    from
    $294Fare subject to changes
    Updated: 1 hour ago
    Round trip
    I
    Economy

    Phoenix (PHX)to

    Flagstaff (FLG)
    07/01/25 - 07/08/25
    from
    $192Fare subject to changes
    Updated: 56 minutes ago
    Round trip
    I
    Economy

    Los Angeles (LAX)to

    Denver (DEN)
    05/09/25 - 05/16/25
    from
    $157Fare subject to changes
    Updated: 1 hour ago
    Round trip
    I
    Economy

  • Philadelphia (PHL)to

    Orlando (MCO)
    05/10/25 - 05/13/25
    from
    $169Fare subject to changes
    Updated: 40 minutes ago
    Round trip
    I
    Economy

    Phoenix (PHX)to

    Miami (MIA)
    04/29/25 - 04/30/25
    from
    $259Fare subject to changes
    Updated: 2 hours ago
    Round trip
    I
    Economy

    Dallas (DFW)to

    Las Vegas (LAS)
    06/07/25 - 06/14/25
    from
    $159Fare subject to changes
    Updated: 1 hour ago
    Round trip
    I
    Economy

    Los Angeles (LAX)to

    Melbourne (MEL)
    05/20/25 - 06/03/25
    from
    $1,410Fare subject to changes
    Updated: 58 minutes ago
    Round trip
    I
    Economy

  • Dallas (DFW)to

    Orlando (MCO)
    07/09/25 - 07/16/25
    from
    $183Fare subject to changes
    Updated: 6 minutes ago
    Round trip
    I
    Economy

    Miami (MIA)to

    Madrid (MAD)
    04/28/25 - 05/20/25
    from
    $547Fare subject to changes
    Updated: 2 hours ago
    Round trip
    I
    Economy

    Dallas (DFW)to

    Cancun (CUN)
    07/15/25 - 07/22/25
    from
    $276Fare subject to changes
    Updated: 48 minutes ago
    Round trip
    I
    Economy

    Dallas (DFW)to

    Boston (BOS)
    05/24/25 - 05/31/25
    from
    $217Fare subject to changes
    Updated: 39 minutes ago
    Round trip
    I
    Economy

  • Dallas (DFW)to

    Chicago (ORD)
    05/06/25 - 05/13/25
    from
    $147Fare subject to changes
    Updated: 1 hour ago
    Round trip
    I
    Economy

    Dallas (DFW)to

    Seattle (SEA)
    05/06/25 - 05/20/25
    from
    $189Fare subject to changes
    Updated: 2 hours ago
    Round trip
    I
    Economy

    Los Angeles (LAX)to

    Tokyo (TYO)
    04/30/25 - 05/07/25
    from
    $882Fare subject to changes
    Updated: 35 minutes ago
    Round trip
    I
    Economy

    Los Angeles (LAX)to

    London (LHR)
    05/10/25 - 05/17/25
    from
    $594Fare subject to changes
    Updated: 1 hour ago
    Round trip
    I
    Economy