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Cayman Islands

$180+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Cayman Islands

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Cayman Islands (KY0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2024.

Round-trip from

$575
(Kiwi.com)

One-way from

$180
(Kiwi.com)
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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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 December 18, 2024.

This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/319:35 pmORD - GCM
2 stops17h 35mMultiple Airlines
Sat 2/1511:30 amGCM - ORD
1 stop11h 55mMultiple Airlines
Deal found 12/17$586
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/318:48 amORD - GCM
Nonstop3h 57mUnited Airlines
Sat 2/152:40 pmGCM - ORD
Nonstop4h 16mUnited Airlines
Deal found 12/17$699
This Southwest deal was found by Cheapflights users on 12/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/225:45 amORD - GCM
1 stop6h 10mSouthwest
Mon 12/301:50 pmGCM - ORD
1 stop9h 10mSouthwest
Deal found 12/17$724
This Air Canada deal was found by Cheapflights users on 12/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/228:25 pmORD - GCM
1 stop16h 15mAir Canada
Mon 12/302:40 pmGCM - ORD
2 stops21h 14mAir Canada
Deal found 12/17$775
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/316:55 pmORD - GCM
1 stop16h 05mAmerican Airlines
Tue 1/73:15 pmGCM - ORD
2 stops9h 54mAmerican Airlines
Deal found 12/17$783
This Delta deal was found by Cheapflights users on 12/16. 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.
Tue 12/245:40 amORD - GCM
1 stop5h 47mDelta
Wed 1/13:47 pmGCM - ORD
1 stop9h 09mDelta
Deal found 12/16$818
This Justfly.com deal was found by Cheapflights users on 12/17. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/3010:00 pmORD - GCM
2 stops41h 55mBritish Airways
Fri 1/36:50 pmGCM - ORD
2 stops20h 55mBritish Airways
Deal found 12/17$7,264

Find flights from O'Hare Intl to Cayman Islands within your budget

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 December 18, 2024.

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Depart

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Price

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 2/6

10:29 am-6:40 pm

1 stop7h 11m

George Town Owen Roberts Intl

Sun 2/9

12:40 pm-10:27 pm

2 stops34h 47m

$575

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 1/16

3:35 pm-1:40 pm

2 stops21h 05m

George Town Owen Roberts Intl

Thu 1/23

2:40 pm-8:57 am

1 stop19h 17m

$580

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 1/2

5:45 am-12:55 pm

1 stop6h 10m

George Town Owen Roberts Intl

Thu 1/9

1:50 pm-10:20 pm

2 stops9h 30m

$589

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 4/6

8:45 am-12:40 pm

Nonstop3h 55m

George Town Owen Roberts Intl

Wed 4/9

1:35 pm-11:13 pm

1 stop9h 38m

$594

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 2/26

5:45 am-12:38 pm

1 stop5h 53m

George Town Owen Roberts Intl

Tue 3/11

12:50 pm-9:15 pm

1 stop8h 25m

$598

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 2/26

5:10 am-4:20 pm

2 stops10h 10m

George Town Owen Roberts Intl

Wed 3/5

1:00 pm-10:12 pm

1 stop10h 12m

$603

ChicagoCayman Brac

ORD - CYB

ORDCYB

Chicago O'Hare Intl

Wed 2/26

8:30 pm-8:05 am

2 stops34h 35m

Cayman Brac Gerrard-Smith

Mon 3/3

8:30 am-9:01 am

2 stops25h 31m

$880

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 1/21

2:02 pm-4:10 pm

1 stop25h 08m

$180

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 3/15

8:30 pm-1:40 pm

1 stop17h 10m

$214

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 3/18

5:45 pm-11:50 am

2 stops18h 05m

$261

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 14 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.

Travel insights for flights from O'Hare Intl to Cayman Islands

Get recent, data-driven insights about flights from O'Hare Intl to Cayman Islands including ideal travel times, pricing trends, and more.

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 $467). Flying from Chicago O'Hare Intl Airport to Cayman Islands in June is currently the most expensive (average of $558). 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 December 18, 2024.

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 December 18, 2024.
Read reviews from past customers who have flown Air Canada, Delta and American Airlines from Chicago to Cayman Islands. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,059 reviews
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Air Canada
7.0
Good
8,382 reviews
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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.

  • 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 ($214), Southwest ($261), and Delta ($292).

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

    On average you can expect to pay $528 for a flight from Chicago O'Hare Intl Airport to Cayman Islands. The cheapest flight overall is $314 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $482.

  • 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 $467). Flying from Chicago O'Hare Intl Airport to Cayman Islands in June is currently the most expensive (average of $558). 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.

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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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$351Average$501FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$367Average$613FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$429Average$683FlexibilityNo cancel feeOn-time69%
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