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Popular Chicago to Cayman Islands flight itineraries

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Budget

Journey type

Chicago (ORD)to
Grand Cayman (GCM)
10/07/25 - 10/14/25
from
$446Fare subject to changes
Updated: 59 minutes ago
Round trip
Economy

*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.

Popular Flights

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	02/04/26 - 02/11/26	from $437Fare subject to changes Updated: 17 hours ago

From
To
Fare type
Travel dates
Price

Chicago (ORD)

Grand Cayman (GCM)

Round trip

Economy

02/04/26 - 02/11/26

from

$437

Updated: 17 hours ago

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From	To	Fare type	Travel dates	Price
Chicago (ORD)	Tokyo (TYO)	Round trip I Premium Economy	03/20/26 - 03/29/26	from $3,747Fare subject to changes Updated: 7 hours ago
Chicago (ORD)	Los Angeles (LAX)	Round trip I Premium Economy	10/11/25 - 10/18/25	from $906Fare subject to changes Updated: 16 hours ago
Chicago (ORD)	London (LHR)	Round trip I Premium Economy	11/19/25 - 12/16/25	from $1,450Fare subject to changes Updated: 8 hours ago
Chicago (ORD)	Tokyo (HND)	Round trip I Premium Economy	11/20/25 - 11/30/25	from $9,391Fare subject to changes Updated: 14 hours ago
Chicago (ORD)	Tokyo (NRT)	Round trip I Premium Economy	03/16/26 - 03/25/26	from $4,160Fare subject to changes Updated: 17 hours ago
Chicago (ORD)	Rome (FCO)	Round trip I Premium Economy	03/14/26 - 03/19/26	from $1,610Fare subject to changes Updated: 1 hour ago
Chicago (ORD)	Madrid (MAD)	Round trip I Premium Economy	01/06/26 - 01/15/26	from $1,269Fare subject to changes Updated: 1 hour ago
Chicago (ORD)	Athens (ATH)	Round trip I Premium Economy	02/02/26 - 02/23/26	from $1,444Fare subject to changes Updated: 10 hours ago
Chicago (ORD)	Barcelona (BCN)	Round trip I Premium Economy	01/06/26 - 04/25/26	from $1,610Fare subject to changes Updated: 17 hours ago
Chicago (ORD)	Honolulu (HNL)	Round trip I Premium Economy	01/15/26 - 01/19/26	from $1,482Fare subject to changes Updated: 12 hours ago
Chicago (ORD)	Paris (CDG)	Round trip I Premium Economy	10/28/25 - 11/04/25	from $1,408Fare subject to changes Updated: 17 hours ago
Chicago (ORD)	Dublin (DUB)	Round trip I Premium Economy	01/12/26 - 01/26/26	from $1,413Fare subject to changes Updated: 7 hours ago
Chicago (ORD)	London (LON)	Round trip I Premium Economy	11/04/25 - 11/11/25	from $1,450Fare subject to changes Updated: 2 hours ago
Chicago (ORD)	Delhi (DEL)	Round trip I Premium Economy	12/14/25 - 12/22/25	from $3,369Fare subject to changes Updated: 9 hours ago
Chicago (ORD)	Maui (OGG)	Round trip I Premium Economy	03/18/26 - 03/24/26	from $2,180Fare subject to changes Updated: 1 hour ago
Chicago (ORD)	Kona (KOA)	Round trip I Premium Economy	10/19/25 - 10/26/25	from $2,415Fare subject to changes Updated: 17 hours ago
Chicago (ORD)	Lisbon (LIS)	Round trip I Premium Economy	12/17/25 - 12/23/25	from $1,806Fare subject to changes Updated: 16 hours ago
Chicago (ORD)	Hong Kong (HKG)	Round trip I Premium Economy	11/01/25 - 11/30/25	from $4,809Fare subject to changes Updated: 12 hours ago
Chicago (ORD)	Amsterdam (AMS)	Round trip I Premium Economy	11/29/25 - 12/06/25	from $1,919Fare subject to changes Updated: 17 hours ago
Chicago (CHI)	London (LON)	Round trip I Premium Economy	11/14/25 - 11/24/25	from $1,570Fare subject to changes Updated: 15 hours ago

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

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From

Dates

Budget

Dallas (DFW)to
New York (LGA)
11/11/25 - 11/18/25
from
$179Fare subject to changes
Updated: 1 hour ago
Round trip
Economy
New York (JFK)to
London (LHR)
10/19/25 - 10/29/25
from
$488Fare subject to changes
Updated: 1 hour ago
Round trip
Economy
Dallas (DFW)to
London (LHR)
09/30/25 - 10/07/25
from
$487Fare subject to changes
Updated: 49 minutes ago
Round trip
Economy
Phoenix (PHX)to
Miami (MIA)
10/29/25 - 11/05/25
from
$159Fare subject to changes
Updated: 59 minutes ago
Round trip
Economy
Dallas (DFW)to
Los Angeles (LAX)
11/05/25 - 11/12/25
from
$199Fare subject to changes
Updated: 1 hour ago
Round trip
Economy
Rome (FCO)to
Dallas (DFW)
10/19/25 - 11/02/25
from
$1,190Fare subject to changes
Updated: 1 hour ago
Round trip
Economy
Los Angeles (LAX)to
New York (JFK)
11/05/25 - 11/12/25
from
$227Fare subject to changes
Updated: 2 hours ago
Round trip
Economy
Dallas (DFW)to
Miami (MIA)
10/19/25 - 10/22/25
from
$159Fare subject to changes
Updated: 1 hour ago
Round trip
Economy
Dallas (DFW)to
Las Vegas (LAS)
10/19/25 - 10/21/25
from
$151Fare subject to changes
Updated: 46 minutes ago
Round trip
Economy
Philadelphia (PHL)to
Orlando (MCO)
12/06/25 - 12/13/25
from
$159Fare subject to changes
Updated: 2 hours ago
Round trip
Economy
Chicago (ORD)to
Tokyo (TYO)
12/02/25 - 12/09/25
from
$1,263Fare subject to changes
Updated: 45 minutes ago
Round trip
Economy
Dallas (DFW)to
Orlando (MCO)
12/10/25 - 12/17/25
from
$159Fare subject to changes
Updated: 1 hour ago
Round trip
Economy
Dallas (DFW)to
Cancun (CUN)
12/15/25 - 12/17/25
from
$261Fare subject to changes
Updated: 2 hours ago
Round trip
Economy
Dallas (DFW)to
Chicago (ORD)
10/11/25 - 10/18/25
from
$157Fare subject to changes
Updated: 1 hour ago
Round trip
Economy
Los Angeles (LAX)to
Tokyo (TYO)
10/21/25 - 10/28/25
from
$677Fare subject to changes
Updated: 2 hours ago
Round trip
Economy
Chicago (ORD)to
Phoenix (PHX)
10/21/25 - 11/04/25
from
$199Fare subject to changes
Updated: 54 minutes ago
Round trip
Economy
Los Angeles (LAX)to
Denver (DEN)
12/09/25 - 12/16/25
from
$137Fare subject to changes
Updated: 1 hour ago
Round trip
Economy
Chicago (ORD)to
Miami (MIA)
12/08/25 - 12/15/25
from
$157Fare subject to changes
Updated: 2 hours ago
Round trip
Economy
New York (NYC)to
Tokyo (TYO)
11/05/25 - 11/12/25
from
$801Fare subject to changes
Updated: 54 minutes ago
Round trip
Economy
Philadelphia (PHL)to
Las Vegas (LAS)
10/25/25 - 11/01/25
from
$277Fare subject to changes
Updated: 58 minutes ago
Round trip
Economy

QA FE Asset in CP VGA-2437

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QA FE BUG-2112 Prepro__ Miami

QA FE BUG-2112 Prepro__ Los Angeles

QA FE BUG-2112 Prepro__ New York

QA FE BUG-2112 Prepro__ Las Vegas

QA FE BUG-2112 Prepro__ Orlando

QA FE BUG-2112 Prepro__ Denver

QA FE BUG-2112 Prepro__ Cancun

QA FE BUG-2112 Prepro__ Chicago

QA FE BUG-2112 Prepro__ Madrid

QA FE BUG-2112 Prepro__ Phoenix

QA FE BUG-2112 Prepro__ Boston

QA FE BUG-2112 Prepro__ Amarillo

QA FE BUG-2112 Prepro__ Tokyo

QA FE BUG-2112 Prepro__ Havana

QA FE BUG-2112 Prepro__ Dallas

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From

Budget

Dallas (DFW)to
New York (LGA)
12/03/25 - 12/10/25
from
$179Fare subject to changes
Updated: 1 hour ago
Round trip
Economy
New York (JFK)to
London (LHR)
10/19/25 - 10/29/25
from
$488Fare subject to changes
Updated: 1 hour ago
Round trip
Economy
Dallas (DFW)to
London (LHR)
10/01/25 - 10/08/25
from
$487Fare subject to changes
Updated: 49 minutes ago
Round trip
Economy
Phoenix (PHX)to
Miami (MIA)
10/29/25 - 11/05/25
from
$159Fare subject to changes
Updated: 59 minutes ago
Round trip
Economy
Dallas (DFW)to
Los Angeles (LAX)
11/08/25 - 11/15/25
from
$199Fare subject to changes
Updated: 1 hour ago
Round trip
Economy
Rome (FCO)to
Dallas (DFW)
10/19/25 - 11/02/25
from
$1,190Fare subject to changes
Updated: 1 hour ago
Round trip
Economy
Los Angeles (LAX)to
New York (JFK)
11/05/25 - 11/12/25
from
$227Fare subject to changes
Updated: 2 hours ago
Round trip
Economy
Dallas (DFW)to
Miami (MIA)
10/19/25 - 10/22/25
from
$159Fare subject to changes
Updated: 1 hour ago
Round trip
Economy
Dallas (DFW)to
Las Vegas (LAS)
10/19/25 - 10/21/25
from
$151Fare subject to changes
Updated: 46 minutes ago
Round trip
Economy
Philadelphia (PHL)to
Orlando (MCO)
12/09/25 - 12/16/25
from
$159Fare subject to changes
Updated: 2 hours ago
Round trip
Economy
Chicago (ORD)to
Tokyo (TYO)
11/18/25 - 11/25/25
from
$1,263Fare subject to changes
Updated: 45 minutes ago
Round trip
Economy
Dallas (DFW)to
Orlando (MCO)
12/09/25 - 12/16/25
from
$159Fare subject to changes
Updated: 1 hour ago
Round trip
Economy
Dallas (DFW)to
Cancun (CUN)
12/15/25 - 12/17/25
from
$261Fare subject to changes
Updated: 2 hours ago
Round trip
Economy
Dallas (DFW)to
Chicago (ORD)
11/20/25 - 11/27/25
from
$157Fare subject to changes
Updated: 1 hour ago
Round trip
Economy
Los Angeles (LAX)to
Tokyo (TYO)
12/03/25 - 12/10/25
from
$677Fare subject to changes
Updated: 2 hours ago
Round trip
Economy
Chicago (ORD)to
Phoenix (PHX)
10/21/25 - 11/04/25
from
$199Fare subject to changes
Updated: 54 minutes ago
Round trip
Economy
Los Angeles (LAX)to
Denver (DEN)
10/28/25 - 11/04/25
from
$137Fare subject to changes
Updated: 1 hour ago
Round trip
Economy
Chicago (ORD)to
Miami (MIA)
12/08/25 - 12/15/25
from
$157Fare subject to changes
Updated: 2 hours ago
Round trip
Economy
New York (NYC)to
Tokyo (TYO)
11/05/25 - 11/12/25
from
$801Fare subject to changes
Updated: 54 minutes ago
Round trip
Economy
Philadelphia (PHL)to
Las Vegas (LAS)
11/04/25 - 11/11/25
from
$277Fare subject to changes
Updated: 58 minutes ago
Round trip
Economy

Testing VGA-2198 Headline Subtitle Ania Liz 12,000Miles*+taxes and fees

Popular Chicago to Cayman Islands flight itineraries

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