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Cayman Islands

$203+ 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Apr 1 — Apr 81
Tue 4/1
Tue 4/8
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 March 27, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$534
(Booking.com)

One-way from

$203
(Mytrip)

Popular in

March

Cheapest in

September

Average price

$868

Good round-trip deal

$745 or less

Good one-way deal

$358 or less
Provider with most accurate pricing for Chicago (CHI)-George Town Owen Roberts Intl flight deals.
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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. 8% potential increase in price ($62 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 27, 2025.

This Booking.com deal was found by Cheapflights users on 3/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/146:15 pmORD - GCM
2 stops41h 40mAir Canada
Thu 6/1912:50 pmGCM - ORD
1 stop22h 03mAir Canada
Deal found 3/26$534
This Trip.com deal was found by Cheapflights users on 3/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/88:17 amORD - GCM
1 stop13h 03mMultiple Airlines
Thu 5/1512:50 pmGCM - ORD
1 stop20h 00mMultiple Airlines
Deal found 3/26$545
This Delta deal was found by Cheapflights users on 3/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/96:00 amORD - GCM
1 stop5h 37mDelta
Tue 11/182:02 pmGCM - ORD
1 stop10h 53mDelta
Deal found 3/26$602
This Southwest deal was found by Cheapflights users on 3/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/166:00 amORD - GCM
1 stop5h 50mSouthwest
Fri 6/2012:45 pmGCM - ORD
2 stops20h 40mSouthwest
Deal found 3/26$606
This American Airlines deal was found by Cheapflights users on 3/26. 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.
Sat 4/267:17 pmORD - GCM
1 stop15h 52mAmerican Airlines
Wed 4/302:00 pmGCM - ORD
1 stop6h 58mAmerican Airlines
Deal found 3/26$610
This United Airlines deal was found by Cheapflights users on 3/26. 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.
Thu 4/245:15 amORD - GCM
1 stop7h 15mUnited Airlines
Sun 4/271:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
Deal found 3/26$625

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 March 27, 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 6/14

6:15 pm-11:55 am

2 stops41h 40m

George Town Owen Roberts Intl

Thu 6/19

12:50 pm-10:53 am

1 stop22h 03m

$534

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 5/8

8:17 am-9:20 pm

1 stop13h 03m

George Town Owen Roberts Intl

Thu 5/15

12:50 pm-8:50 am

1 stop20h 00m

$545

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 6/16

5:25 pm-11:50 am

2 stops18h 25m

George Town Owen Roberts Intl

Fri 6/20

12:45 pm-9:25 am

2 stops20h 40m

$606

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 4/26

7:17 pm-11:09 am

1 stop15h 52m

George Town Owen Roberts Intl

Wed 4/30

2:00 pm-8:58 pm

1 stop6h 58m

$610

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 4/24

5:15 am-12:30 pm

1 stop7h 15m

George Town Owen Roberts Intl

Sun 4/27

1:45 pm-6:07 pm

Nonstop4h 22m

$625

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 4/6

5:45 am-11:25 am

1 stop5h 40m

George Town Owen Roberts Intl

Sat 4/12

2:45 pm-11:59 pm

1 stop9h 14m

$3,375

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 6/14

6:15 pm-11:55 am

2 stops41h 40m

$218

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 7/7

7:00 am-9:20 pm

1 stop14h 20m

$227

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 4/27

8:45 am-12:40 pm

Nonstop3h 55m

$288

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 5/10

6:35 pm-11:20 am

1 stop16h 45m

$293

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

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 $467). Flying from Chicago O'Hare Intl Airport to Cayman Islands in March is currently the most expensive (average of $594). 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 March 27, 2025.

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 March 27, 2025.
Southwest
8.1
Very good
4,273 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,273 reviews
Southwest
8.1
Very good
4,273 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,895 reviews
Southwest
8.1
Very good
4,273 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,603 reviews
Southwest
8.1
Very good
4,273 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,273 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Air Canada
7.0
Good
8,973 reviews
Southwest
8.1
Very good
4,273 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 ($218), United Airlines ($288), and American Airlines ($293).

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

    On average you can expect to pay $675 for a flight from Chicago O'Hare Intl Airport to Cayman Islands. The cheapest flight overall is $313 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $503.

  • 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 March is currently the most expensive (average of $594). 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 March 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$463Average$628FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$468Average$662FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$506Average$703FlexibilityNo cancel feeOn-time69%
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