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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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
feb. 4 — feb. 111
mar. 2/4
mar. 2/11
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 enero 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$595
(United Airlines)

One-way from

$169
(Southwest)

Popular in

March

Cheapest in

September

Average price

$613

Good round-trip deal

$686 or less

Good one-way deal

$332 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. 7% potential increase in price ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in January 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 enero 30, 2025.

This Mytrip deal was found by Cheapflights users on 1/30. 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.
mié. 4/25:55 amORD - GCM
3 stops30h 30mMultiple Airlines
mié. 4/911:30 amGCM - ORD
2 stops20h 10mMultiple Airlines
Deal found 1/30$593
This United Airlines deal was found by Cheapflights users on 1/29. 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.
mar. 3/118:48 amORD - GCM
Nonstop3h 57mUnited Airlines
mar. 3/181:50 pmGCM - ORD
Nonstop4h 16mUnited Airlines
Deal found 1/29$595
This Priceline deal was found by Cheapflights users on 1/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/276:13 pmORD - GCM
2 stops18h 27mAir Canada
dom. 3/24:00 pmGCM - ORD
1 stop19h 04mAir Canada
Deal found 1/29$597
This American Airlines deal was found by Cheapflights users on 1/29. 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.
dom. 3/236:58 pmORD - GCM
1 stop16h 02mAmerican Airlines
jue. 4/312:00 pmGCM - ORD
1 stop12h 20mAmerican Airlines
Deal found 1/29$600
This Delta deal was found by Cheapflights users on 1/28. 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.
mié. 2/265:45 amORD - GCM
1 stop5h 53mDelta
mié. 3/52:04 pmGCM - ORD
1 stop10h 45mDelta
Deal found 1/28$610

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 enero 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 4/2

5:55 am-12:25 pm

3 stops30h 30m

George Town Owen Roberts Intl

mié. 4/9

11:30 am-7:40 am

2 stops20h 10m

$593

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mar. 3/11

8:48 am-12:45 pm

Nonstop3h 57m

George Town Owen Roberts Intl

mar. 3/18

1:50 pm-6:06 pm

Nonstop4h 16m

$595

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

jue. 2/27

6:13 pm-1:40 pm

2 stops18h 27m

George Town Owen Roberts Intl

dom. 3/2

4:00 pm-10:04 am

1 stop19h 04m

$597

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

dom. 3/23

6:58 pm-11:00 am

1 stop16h 02m

George Town Owen Roberts Intl

jue. 4/3

3:34 pm-7:22 am

1 stop15h 48m

$600

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 2/26

5:45 am-12:38 pm

1 stop5h 53m

George Town Owen Roberts Intl

mar. 3/11

1:03 pm-11:56 pm

1 stop10h 53m

$610

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mar. 4/29

6:00 am-11:50 am

1 stop5h 50m

$169

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

jue. 2/27

11:46 am-9:20 pm

1 stop8h 34m

$175

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

vie. 2/28

6:45 pm-7:03 pm

1 stop23h 18m

$189

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

lun. 4/28

2:05 pm-12:25 pm

1 stop22h 20m

$211

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

jue. 5/22

5:30 pm-12:45 pm

2 stops43h 15m

$286

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 13 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 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 enero 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 enero 30, 2025.
Read reviews from past customers who have flown Southwest, Delta and United 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
4,585 reviews

Boarding

8.2

Entertainment

7.7

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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
4,585 reviews
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Entertainment

7.7

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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
8,454 reviews
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Entertainment

7.7

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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
8,913 reviews
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Entertainment

7.7

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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
4,585 reviews

Boarding

8.2

Entertainment

7.7

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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
8,640 reviews
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Entertainment

7.7

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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 Southwest ($169), Sun Country Air ($189), and Air Canada ($211).

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

    On average you can expect to pay $575 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 $453.

  • 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 enero 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$351Average$494FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$453Average$647FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$469Average$701FlexibilityNo cancel feeOn-time69%
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