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Cayman Islands

$169+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
may. 5 — may. 121
lun. 5/5
lun. 5/12
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 abril 30, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$473
(Kiwi.com)

One-way from

$195
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$648

Good round-trip deal

$735 or less

Good one-way deal

$313 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. 8% potential increase in price ($62 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in April 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 abril 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
sáb. 10/43:11 pmORD - GCM
1 stop20h 29mMultiple Airlines
mié. 10/811:30 amGCM - ORD
1 stop11h 17mMultiple Airlines
Deal found 4/29$464
This Air Canada deal was found by Cheapflights users on 4/29. 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.
dom. 6/18:25 pmORD - GCM
1 stop15h 30mAir Canada
jue. 6/512:50 pmGCM - ORD
1 stop9h 15mAir Canada
Deal found 4/29$511
This Southwest deal was found by Cheapflights users on 4/29. 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.
sáb. 9/66:00 amORD - GCM
1 stop6h 10mSouthwest
sáb. 9/131:10 pmGCM - ORD
1 stop8h 20mSouthwest
Deal found 4/29$576
This Delta deal was found by Cheapflights users on 4/29. 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.
lun. 7/145:35 amORD - GCM
1 stop5h 50mDelta
mar. 7/2212:40 pmGCM - ORD
1 stop8h 50mDelta
Deal found 4/29$610
This American Airlines deal was found by Cheapflights users on 4/29. 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. 5/285:00 amORD - GCM
1 stop6h 10mAmerican Airlines
mar. 6/312:10 pmGCM - ORD
2 stops11h 46mAmerican Airlines
Deal found 4/29$614
This United Airlines deal was found by Cheapflights users on 4/29. 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. 7/269:26 amORD - GCM
Nonstop4h 04mUnited Airlines
sáb. 8/21:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
Deal found 4/29$645
This WestJet deal was found by Cheapflights users on 4/29. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 7/131:40 pmORD - GCM
2 stops47h 05mWestJet
mar. 7/221:45 pmGCM - ORD
2 stops26h 59mWestJet
Deal found 4/29$792

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 abril 30, 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

sáb. 10/4

3:11 pm-11:40 am

1 stop20h 29m

George Town Owen Roberts Intl

mié. 10/8

11:30 am-10:47 pm

1 stop11h 17m

$464

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

dom. 6/1

8:25 pm-11:55 am

1 stop15h 30m

George Town Owen Roberts Intl

jue. 6/5

12:50 pm-10:05 pm

1 stop9h 15m

$511

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

sáb. 9/6

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

sáb. 9/13

1:10 pm-9:30 pm

1 stop8h 20m

$576

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

lun. 7/14

5:35 am-11:25 am

1 stop5h 50m

George Town Owen Roberts Intl

mié. 7/23

12:40 pm-9:30 pm

1 stop8h 50m

$610

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 5/28

5:00 am-11:10 am

1 stop6h 10m

George Town Owen Roberts Intl

mar. 6/3

12:10 pm-11:56 pm

2 stops11h 46m

$614

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

sáb. 7/26

9:26 am-1:30 pm

Nonstop4h 04m

George Town Owen Roberts Intl

sáb. 8/2

1:45 pm-6:07 pm

Nonstop4h 22m

$645

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

dom. 7/13

1:40 pm-12:45 pm

2 stops47h 05m

George Town Owen Roberts Intl

mar. 7/22

1:45 pm-4:44 pm

2 stops26h 59m

$792

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 5/21

3:45 pm-4:10 pm

3 stops48h 25m

George Town Owen Roberts Intl

lun. 5/26

6:05 pm-7:00 pm

3 stops24h 55m

$8,842

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

dom. 6/1

8:17 am-11:40 am

1 stop27h 23m

$169

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 5/28

9:14 pm-11:55 am

1 stop14h 41m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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.

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 abril 30, 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 abril 30, 2025.
Southwest
8.0
Very good
4,295 reviews

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,936 reviews
Southwest
8.0
Very good
4,295 reviews

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,295 reviews

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,295 reviews

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
WestJet
7.2
Good
2,823 reviews
Southwest
8.0
Very good
4,295 reviews

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 ($197), Southwest ($291), and Delta ($293).

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

    On average you can expect to pay $605 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 $537.

  • 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 abril 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$463Average$668FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$467Average$662FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$501Average$705FlexibilityNo cancel feeOn-time69%

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