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Cayman Islands

$167+ 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
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 November 20, 2024.

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 November 20, 2024.

This Mytrip deal was found by Cheapflights users on 11/20. 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 12/116:37 pmORD - GCM
1 stop17h 23mMultiple Airlines
Sun 12/154:00 pmGCM - ORD
2 stops17h 02mMultiple Airlines
Deal found 11/20$562
This United Airlines deal was found by Cheapflights users on 11/19. 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.
Wed 12/187:35 amORD - GCM
1 stop7h 50mUnited Airlines
Wed 12/252:50 pmGCM - ORD
Nonstop4h 16mUnited Airlines
Deal found 11/19$608
This Priceline deal was found by Cheapflights users on 11/19. 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 12/59:50 amORD - GCM
1 stop26h 50mAir Canada
Sun 12/84:00 pmGCM - ORD
1 stop28h 32mAir Canada
Deal found 11/19$617
This Delta deal was found by Cheapflights users on 11/19. 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 12/317:05 amORD - GCM
1 stop6h 16mDelta
Thu 1/92:09 pmGCM - ORD
1 stop10h 50mDelta
Deal found 11/19$618
This American Airlines deal was found by Cheapflights users on 11/19. 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 1/71:00 pmGCM - ORD
2 stops10h 04mAmerican Airlines
Deal found 11/19$623
This Southwest deal was found by Cheapflights users on 11/19. 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.
Tue 11/265:45 amORD - GCM
1 stop6h 10mSouthwest
Tue 12/31:50 pmGCM - ORD
2 stops9h 10mSouthwest
Deal found 11/19$659
This CheapOair deal was found by Cheapflights users on 11/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/228:25 pmORD - CYB
2 stops34h 40mMultiple Airlines
Sat 12/286:00 pmCYB - ORD
2 stops45h 51mMultiple Airlines
Deal found 11/20$1,006

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 2,629,791 searches. Data last updated November 20, 2024.

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Price

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 1/22

5:06 pm-1:00 pm

1 stop18h 54m

George Town Owen Roberts Intl

Tue 1/28

11:30 am-12:45 pm

2 stops26h 15m

$462

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

$531

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 3/18

8:48 am-12:45 pm

Nonstop3h 57m

George Town Owen Roberts Intl

Tue 3/25

1:50 pm-6:06 pm

Nonstop4h 16m

$574

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 2/1

6:30 pm-12:35 pm

1 stop17h 05m

George Town Owen Roberts Intl

Wed 2/5

1:40 pm-12:09 am

1 stop11h 29m

$588

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/11

3:35 pm-3:00 pm

2 stops22h 25m

George Town Owen Roberts Intl

Sun 1/19

4:00 pm-10:54 am

2 stops19h 54m

$594

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 2/21

6:15 am-2:35 pm

1 stop7h 20m

George Town Owen Roberts Intl

Wed 2/26

2:09 pm-11:59 pm

1 stop10h 50m

$613

ChicagoCayman Brac

ORD - CYB

ORDCYB

Chicago O'Hare Intl

Sun 12/22

8:25 pm-8:05 am

2 stops34h 40m

Cayman Brac Gerrard-Smith

Sat 12/28

6:00 pm-2:51 pm

2 stops45h 51m

$1,006

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 1/22

5:06 pm-1:00 pm

1 stop18h 54m

$167

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 5/19

6:00 am-11:50 am

1 stop5h 50m

$211

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 5/17

4:00 pm-11:30 am

1 stop19h 30m

$228

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 16 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 $560). 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 November 20, 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 November 20, 2024.
Read reviews from past customers who have flown Air Canada, Delta and Southwest 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
5,014 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,811 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 ($261), Sun Country Air ($272), 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 $570 for a flight from Chicago O'Hare Intl Airport to Cayman Islands. The cheapest flight overall is $296 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $462.

  • 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 $560). 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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$348Average$476FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$368Average$606FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$420Average$671FlexibilityNo cancel feeOn-time69%
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