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Cayman Islands

$72+ 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
ene. 11 — ene. 181
dom. 1/11
dom. 1/18
1 adult, Economy
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Cheap 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 diciembre 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/313:26 pmORD - GCM
1 stop21h 19mMultiple Airlines
mié. 1/711:30 amGCM - ORD
1 stop21h 48mMultiple Airlines
Deal found 12/9$371
This United Airlines deal was found by Cheapflights users on 12/10. 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.
lun. 12/228:45 amORD - GCM
Nonstop4h 00mUnited Airlines
jue. 12/252:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 12/10$438
This Kiwi.com deal was found by Cheapflights users on 12/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/226:05 pmORD - GCM
1 stop16h 30mMultiple Airlines
jue. 12/252:40 pmGCM - ORD
1 stop10h 50mMultiple Airlines
Deal found 12/9$448
This Kiwi.com deal was found by Cheapflights users on 12/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/226:05 pmORD - GCM
1 stop16h 30mMultiple Airlines
sáb. 12/275:56 pmGCM - ORD
1 stop7h 34mMultiple Airlines
Deal found 12/9$449
This Delta deal was found by Cheapflights users on 12/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/245:30 amORD - GCM
1 stop6h 06mDelta
jue. 12/251:52 pmGCM - ORD
1 stop11h 10mDelta
Deal found 12/9$452
This Delta deal was found by Cheapflights users on 12/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/237:00 amORD - GCM
2 stops28h 36mDelta
jue. 12/251:52 pmGCM - ORD
1 stop11h 10mDelta
Deal found 12/9$457
This American Airlines deal was found by Cheapflights users on 12/11. 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.
mié. 12/249:24 amORD - GCM
Nonstop4h 11mAmerican Airlines
mié. 12/313:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 12/11$463
This United Airlines deal was found by Cheapflights users on 12/9. 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.
sáb. 12/208:45 amORD - GCM
Nonstop4h 00mUnited Airlines
jue. 12/252:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 12/9$468
This Expedia deal was found by Cheapflights users on 12/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/228:30 pmORD - GCM
1 stop14h 55mAir Canada
jue. 12/251:30 pmGCM - ORD
2 stops30h 23mAir Canada
Deal found 12/10$470
This American Airlines deal was found by Cheapflights users on 12/11. 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.
vie. 12/127:00 amORD - GCM
1 stop6h 44mAmerican Airlines
vie. 12/193:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 12/11$472

Find 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 diciembre 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$247
(FlightHub)

One-way from

$72
(Expedia)

Popular in

December

Cheapest in

October

Average price

$827

Good round-trip deal

$449 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. 6% potential increase in price ($45 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 December 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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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 diciembre 12, 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

mié. 2/25

7:59 pm-1:43 pm

1 stop16h 44m

George Town Owen Roberts Intl

dom. 3/1

2:49 pm-8:54 pm

1 stop7h 05m

$310

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

vie. 1/16

8:43 pm-1:38 pm

1 stop15h 55m

George Town Owen Roberts Intl

lun. 1/19

1:30 pm-8:05 am

2 stops19h 35m

$357

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

lun. 1/26

4:50 pm-12:25 pm

1 stop18h 35m

George Town Owen Roberts Intl

vie. 1/30

1:30 pm-10:05 pm

1 stop9h 35m

$391

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 2/18

7:05 am-1:43 pm

1 stop29h 38m

George Town Owen Roberts Intl

sáb. 2/28

8:50 am-9:39 am

1 stop25h 49m

$411

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 12/24

5:30 am-2:27 pm

1 stop7h 57m

George Town Owen Roberts Intl

mié. 12/31

3:42 pm-12:02 am

1 stop9h 20m

$452

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mar. 3/31

5:45 am-12:30 pm

1 stop6h 45m

George Town Owen Roberts Intl

mar. 4/7

1:35 pm-9:36 pm

1 stop8h 01m

$452

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

dom. 4/26

6:00 am-11:24 am

1 stop5h 24m

George Town Owen Roberts Intl

mié. 4/29

12:45 pm-9:16 pm

1 stop8h 31m

$452

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mar. 1/27

6:00 pm-12:40 pm

2 stops17h 40m

George Town Owen Roberts Intl

jue. 1/29

2:05 pm-9:41 am

2 stops20h 36m

$457

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

dom. 1/25

6:50 am-12:40 pm

2 stops28h 50m

George Town Owen Roberts Intl

mar. 2/3

2:05 pm-9:41 am

2 stops20h 36m

$457

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

jue. 2/12

5:15 am-1:43 pm

1 stop7h 28m

George Town Owen Roberts Intl

dom. 2/15

2:49 pm-8:56 pm

1 stop7h 07m

$472

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 19 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, December is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Cayman Islands (average of $339). 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 diciembre 12, 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 45% 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 diciembre 12, 2025.
Get a feel of what it's like to fly with 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.
United Airlines
7.4
Good
9,095 reviews

Entertainment

7.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
United Airlines
7.4
Good
9,095 reviews
United Airlines
7.4
Good
9,095 reviews

Entertainment

7.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
American Airlines
7.2
Good
11,050 reviews
United Airlines
7.4
Good
9,095 reviews

Entertainment

7.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.

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 16h 44m. Airlines will cover a distance of 1613 mi. This flight may include one or multiple stops.

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

    On average you can expect to pay $590 for a flight from Chicago O'Hare Intl Airport to Cayman Islands. The cheapest flight overall is $339 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $247.

  • 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, December is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Cayman Islands (average of $339). 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 2 airlines flying from O'Hare Intl to Cayman Islands

Discover the top 2 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 diciembre 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$341Average$688FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$459Average$720FlexibilityNo cancel feeOn-time71%

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