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Cayman Islands

$66+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
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 January 26, 2026.

This FlightHub deal was found by Cheapflights users on 1/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/265:15 am
ORD
-
GCM
1 stop7h 28m
Spirit Airlines
Sat 5/21:40 pm
GCM
-
ORD
1 stop10h 01m
Spirit Airlines
Deal found 1/25$344
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/85:15 am
ORD
-
GCM
1 stop7h 38m
Spirit Airlines
Thu 2/122:49 pm
GCM
-
ORD
2 stops18h 05m
Spirit Airlines
Deal found 1/26$345
This Mytrip deal was found by Cheapflights users on 1/24. 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 2/75:15 am
ORD
-
GCM
1 stop7h 23m
Multiple Airlines
Tue 2/101:30 pm
GCM
-
ORD
1 stop21h 36m
Multiple Airlines
Deal found 1/24$346
This Mytrip deal was found by Cheapflights users on 1/24. 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.
Wed 4/18:41 pm
ORD
-
GCM
1 stop16h 16m
Multiple Airlines
Wed 4/811:30 am
GCM
-
ORD
1 stop7h 05m
Multiple Airlines
Deal found 1/24$347
This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Thu 2/195:15 am
ORD
-
GCM
1 stop7h 28m
Spirit Airlines
Sun 2/222:49 pm
GCM
-
ORD
1 stop29h 22m
Spirit Airlines
Deal found 1/24$348
This Mytrip deal was found by Cheapflights users on 1/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/125:05 am
ORD
-
GCM
1 stop7h 52m
Spirit Airlines
Thu 3/191:52 pm
GCM
-
ORD
2 stops21h 55m
Spirit Airlines
Deal found 1/26$349
This Travelocity deal was found by Cheapflights users on 1/26. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/55:15 am
ORD
-
GCM
1 stop7h 38m
Multiple Airlines
Tue 2/101:30 pm
GCM
-
ORD
2 stops30h 25m
Multiple Airlines
Deal found 1/26$351
This Orbitz deal was found by Cheapflights users on 1/25. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:05 am
ORD
-
GCM
1 stop5h 38m
Multiple Airlines
Sat 6/612:25 pm
GCM
-
ORD
1 stop19h 35m
Multiple Airlines
Deal found 1/25$352
This FlightHub deal was found by Cheapflights users on 1/23. 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.
Sat 3/148:41 pm
ORD
-
GCM
1 stop16h 16m
Spirit Airlines
Thu 3/191:52 pm
GCM
-
ORD
1 stop9h 25m
Spirit Airlines
Deal found 1/23$355
This Travelocity deal was found by Cheapflights users on 1/25. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:21 pm
ORD
-
GCM
2 stops41h 09m
Multiple Airlines
Sat 5/91:40 pm
GCM
-
ORD
1 stop10h 01m
Multiple Airlines
Deal found 1/25$357
This Priceline deal was found by Cheapflights users on 1/23. 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 2/125:15 am
ORD
-
GCM
1 stop7h 28m
Spirit Airlines
Sun 2/152:49 pm
GCM
-
ORD
1 stop9h 58m
Spirit Airlines
Deal found 1/23$358
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/179:18 am
ORD
-
GCM
1 stop29h 47m
Multiple Airlines
Sun 2/222:49 pm
GCM
-
ORD
2 stops21h 02m
Multiple Airlines
Deal found 1/25$359

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 January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$344
(FlightHub)

One-way from

$66
(Expedia)

Popular in

December

Cheapest in

October

Average price

$560

Good round-trip deal

$498 or less

Good one-way deal

$288 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
Search Deals
One-way flight from Chicago O'Hare Intl to Cayman Islands
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago O'Hare Intl to Cayman Islands.
Search Deals
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 January 26, 2026.
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 5/2

5:15 am-12:43 pm

1 stop7h 28m

George Town Owen Roberts Intl

Sat 5/9

1:40 pm-11:41 pm

1 stop10h 01m

$344

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 3/16

9:50 am-9:15 pm

1 stop11h 25m

George Town Owen Roberts Intl

Sat 3/21

1:15 pm-11:21 am

1 stop22h 06m

$412

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 2/7

12:50 pm-12:25 pm

2 stops22h 35m

George Town Owen Roberts Intl

Thu 2/12

1:30 pm-12:48 pm

2 stops24h 18m

$420

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 2/20

6:04 am-2:34 pm

1 stop7h 30m

George Town Owen Roberts Intl

Mon 2/23

1:30 pm-12:48 pm

2 stops24h 18m

$454

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 2/8

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Thu 2/12

2:50 pm-6:04 pm

Nonstop4h 14m

$455

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 3/16

8:45 am-12:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Wed 4/1

1:50 pm-6:13 pm

Nonstop4h 23m

$491

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 3/1

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Fri 3/6

2:50 pm-6:04 pm

Nonstop4h 14m

$491

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 3/10

8:41 am-7:15 pm

1 stop10h 34m

George Town Owen Roberts Intl

Wed 3/18

2:44 pm-6:54 pm

Nonstop4h 10m

$495

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 2/24

5:25 am-12:29 pm

1 stop6h 04m

George Town Owen Roberts Intl

Sat 2/28

12:25 pm-7:19 pm

1 stop7h 54m

$499

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 3/22

8:00 am-10:25 am

1 stop26h 25m

George Town Owen Roberts Intl

Sat 3/28

1:15 pm-11:17 pm

1 stop10h 02m

$500

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

Showing 1-10 of 22 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 $322). 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 January 26, 2026.

When flying from Chicago O'Hare Intl Airport to Cayman Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 January 26, 2026.
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
9,199 reviews

Boarding

7.7

Food

6.6

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,199 reviews
United Airlines
7.4
Good
9,199 reviews

Boarding

7.7

Food

6.6

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.2
Good
11,189 reviews
United Airlines
7.4
Good
9,199 reviews

Boarding

7.7

Food

6.6

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 Air Canada ($137), American Airlines ($288), and United Airlines ($288).

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

    On average you can expect to pay $510 for a flight from Chicago O'Hare Intl Airport to Cayman Islands. The cheapest flight overall is $288 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $223.

  • 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 $322). 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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Midway to Castries flights
Midway to Georgetown flights
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Midway to St. John's flights
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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 January 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$341Average$624FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$438Average$707FlexibilityNo cancel feeOn-time71%

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