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Cayman Islands

$101+ Cheap flights from O'Hare Intl (ORD) to the Cayman Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Cayman Islands

Keep the following information in mind while searching for O'Hare Intl to Cayman Islands flight deals. Data was last updated October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$305
(Priceline)

One-way from

$101
(Expedia)

Popular in

December

Cheapest in

October

Average price

$539

Good round-trip deal

$454 or less

Good one-way deal

$582 or less
Provider with most accurate pricing for Chicago (CHI)-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-George Town Owen Roberts Intl flights.
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From Chicago O'Hare Intl to Cayman Islands
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One-way flight from Chicago O'Hare Intl to Cayman Islands
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Highest demand for flights based on searches. 10% potential increase in price ($78 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Chicago O'Hare Intl to Cayman Islands.
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Price to beat on a one-way flight from Chicago O'Hare Intl to Cayman Islands.
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Find flight deals from O'Hare Intl to Cayman Islands

Cheapest flights from O'Hare Intl to Cayman Islands
Explore the most affordable flight options available from O'Hare Intl to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 28, 2025.

This Priceline deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/115:00 amORD - GCM
1 stop7h 45mSpirit Airlines
Thu 12/182:40 pmGCM - ORD
1 stop10h 50mSpirit Airlines
Deal found 10/26$305
This Priceline deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/67:10 amORD - GCM
1 stop8h 45mSpirit Airlines
Sat 12/135:56 pmGCM - ORD
1 stop7h 13mSpirit Airlines
Deal found 10/27$325
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/298:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Sat 12/62:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 10/28$338
This American Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/125:00 amORD - GCM
1 stop8h 06mAmerican Airlines
Fri 12/193:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 10/26$342
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/145:00 amORD - GCM
1 stop6h 00mAmerican Airlines
Sun 12/213:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 10/27$347
This American Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/67:10 amORD - GCM
1 stop6h 12mAmerican Airlines
Sat 12/138:45 amGCM - ORD
1 stop16h 52mAmerican Airlines
Deal found 10/25$352
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/167:10 amORD - GCM
1 stop8h 20mUnited Airlines
Wed 11/195:45 pmGCM - ORD
1 stop16h 26mUnited Airlines
Deal found 10/26$353
This American Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/175:00 amORD - GCM
1 stop14h 28mAmerican Airlines
Thu 11/203:36 pmGCM - ORD
2 stops9h 04mAmerican Airlines
Deal found 10/26$357
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/249:24 amORD - GCM
Nonstop4h 11mAmerican Airlines
Wed 12/313:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 10/27$363
This FlightHub deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/188:15 pmORD - CYB
2 stops17h 55mMultiple Airlines
Sun 12/2110:55 amCYB - ORD
2 stops23h 18mMultiple Airlines
Deal found 10/26$1,292
This Mytrip deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/18:00 amORD - CYB
2 stops48h 05mMultiple Airlines
Sat 11/293:40 pmCYB - ORD
3 stops24h 15mMultiple Airlines
Deal found 10/27$2,250

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Cayman Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 28, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to the Cayman Islands that are best for you.

Fly from

O'Hare Intl

Fly to

Cayman Islands

Route

Depart

Return

Price

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 11/29

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Sat 12/6

2:50 pm-6:04 pm

Nonstop4h 14m

$338

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 2/6

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Fri 2/13

2:50 pm-6:04 pm

Nonstop4h 14m

$342

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 1/12

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Sun 1/18

2:50 pm-6:04 pm

Nonstop4h 14m

$342

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/24

5:30 am-12:36 pm

1 stop6h 06m

George Town Owen Roberts Intl

Wed 12/31

1:52 pm-7:38 pm

1 stop6h 46m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/10

8:49 am-4:30 pm

1 stop6h 41m

George Town Owen Roberts Intl

Sun 12/14

5:45 pm-10:02 am

1 stop17h 17m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 1/7

5:33 am-12:40 pm

1 stop6h 07m

George Town Owen Roberts Intl

Mon 1/12

2:05 pm-7:35 pm

1 stop6h 30m

$356

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 1/6

5:33 am-12:40 pm

1 stop6h 07m

George Town Owen Roberts Intl

Tue 1/13

2:05 pm-7:35 pm

1 stop6h 30m

$356

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 2/3

5:33 am-12:40 pm

1 stop6h 07m

George Town Owen Roberts Intl

Sat 2/7

3:25 pm-11:57 pm

1 stop9h 32m

$356

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 1/11

5:33 am-12:40 pm

1 stop6h 07m

George Town Owen Roberts Intl

Tue 1/13

2:05 pm-7:35 pm

1 stop6h 30m

$356

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 1/18

5:33 am-12:40 pm

1 stop6h 07m

George Town Owen Roberts Intl

Sat 1/24

3:25 pm-11:57 pm

1 stop9h 32m

$356

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 23 results
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Best time to book a flight from O'Hare Intl to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to the Cayman Islands

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Cayman Islands?

Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Cayman Islands (average of $381). Flying from Chicago O'Hare Intl Airport to Cayman Islands in September is currently the most expensive (average of $650). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ORD to KY?

Find hourly flight availability from O'Hare Intl to Cayman Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 28, 2025.

It’s optimal to fly from Chicago O'Hare Intl Airport to Cayman Islands at noon. By choosing this option you can save up to 47% on the cost of your flight, compared to a flight in the morning.

Reviews of airlines servicing Cayman Islands

Get insights into the airlines that provide service to Cayman Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Cayman Islands. Reviews last updated October 28, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Chicago O'Hare Intl Airport to the Cayman Islands by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,994 reviews

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,994 reviews
Delta
7.9
Good
7,994 reviews

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
9,001 reviews
Delta
7.9
Good
7,994 reviews

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,994 reviews

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago O'Hare Intl Airport to Cayman Islands?

    Departing from Chicago O'Hare Intl Airport to Cayman Islands will take you 4h. Airlines will cover a distance of 1613 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Cayman Islands one-way?

    The cheapest airlines for a one-way flight from Chicago O'Hare Intl Airport to Cayman Islands are Spirit Airlines ($101), Air Canada ($136), and Southwest ($163).

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Cayman Islands?

    On average you can expect to pay $644 for a flight from Chicago O'Hare Intl Airport to Cayman Islands. The cheapest flight overall is $341 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $305.

  • Can I find deals for flights from O'Hare Intl to Cayman Islands that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Cayman Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Cayman Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Cayman Islands.

  • Can I find deals for business class flights from O'Hare Intl to Cayman Islands?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Cayman Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Cayman Islands?

    Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Cayman Islands (average of $381). Flying from Chicago O'Hare Intl Airport to Cayman Islands in September is currently the most expensive (average of $650). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for O'Hare Intl to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from O'Hare Intl to Cayman Islands

Discover the top 3 airlines that operate flights from O'Hare Intl to Cayman Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$434Average$722FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$504Average$711FlexibilityNo cancel feeOn-time71%
DeltaCheapest$564Average$798FlexibilityNo cancel feeOn-timeN/A

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