HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Cayman Islands

$181+ 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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from O'Hare Intl to Cayman Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 April 17, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$474
(Kiwi.com)

One-way from

$181
(Kiwi.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.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-George Town Owen Roberts Intl flights.
Search Deals
From Chicago O'Hare Intl to Cayman Islands
Search Deals
One-way flight from Chicago O'Hare Intl to Cayman Islands
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Chicago O'Hare Intl to Cayman Islands.
Search Deals
Price to beat on a one-way flight from Chicago O'Hare Intl to Cayman Islands.
Search Deals

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 April 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Sat 9/273:11 pmORD - GCM
1 stop20h 29mMultiple Airlines
Sat 10/48:50 amGCM - ORD
1 stop13h 57mMultiple Airlines
Deal found 4/17$464
This Justfly.com deal was found by Cheapflights users on 4/17. 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.
Sun 6/18:25 pmORD - GCM
1 stop15h 30mAir Canada
Thu 6/512:50 pmGCM - ORD
2 stops21h 02mAir Canada
Deal found 4/17$497
This United Airlines deal was found by Cheapflights users on 4/17. 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.
Wed 7/27:35 pmORD - GCM
1 stop16h 55mUnited Airlines
Wed 7/91:35 pmGCM - ORD
1 stop10h 40mUnited Airlines
Deal found 4/17$610
This American Airlines deal was found by Cheapflights users on 4/17. 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.
Wed 5/285:00 amORD - GCM
2 stops8h 10mAmerican Airlines
Tue 6/312:10 pmGCM - ORD
1 stop10h 38mAmerican Airlines
Deal found 4/17$614
This Delta deal was found by Cheapflights users on 4/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/255:35 amORD - GCM
1 stop5h 50mDelta
Tue 7/812:50 pmGCM - ORD
1 stop8h 31mDelta
Deal found 4/17$620
This Trip.com deal was found by Cheapflights users on 4/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/18:17 amORD - CYB
2 stops23h 48mMultiple Airlines
Sun 6/88:30 amCYB - ORD
2 stops33h 11mMultiple Airlines
Deal found 4/17$733

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 April 17, 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 9/27

3:11 pm-11:40 am

1 stop20h 29m

George Town Owen Roberts Intl

Sat 10/4

8:50 am-10:47 pm

1 stop13h 57m

$464

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 6/1

8:25 pm-11:55 am

1 stop15h 30m

George Town Owen Roberts Intl

Thu 6/5

12:50 pm-9:52 am

2 stops21h 02m

$497

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 7/2

7:35 pm-12:30 pm

1 stop16h 55m

George Town Owen Roberts Intl

Wed 7/9

1:35 pm-12:15 am

1 stop10h 40m

$610

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 5/28

5:00 am-1:10 pm

2 stops8h 10m

George Town Owen Roberts Intl

Tue 6/3

12:10 pm-10:48 pm

1 stop10h 38m

$614

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 6/25

5:35 am-11:25 am

1 stop5h 50m

George Town Owen Roberts Intl

Tue 7/8

12:50 pm-9:21 pm

1 stop8h 31m

$620

ChicagoCayman Brac

ORD - CYB

ORDCYB

Chicago O'Hare Intl

Sun 6/1

8:17 am-8:05 am

2 stops23h 48m

Cayman Brac Gerrard-Smith

Sun 6/8

8:30 am-5:41 pm

2 stops33h 11m

$733

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 6/17

1:43 pm-4:10 pm

1 stop26h 27m

$181

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 6/1

12:00 pm-11:55 am

1 stop23h 55m

$197

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 6/1

8:17 pm-11:10 am

2 stops14h 53m

$295

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 5/14

5:30 am-11:20 am

1 stop5h 50m

$298

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Showing 1-10 of 12 results
1
2

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 April 17, 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 April 17, 2025.
Read reviews from past customers who have flown Delta, United Airlines 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.
Delta
8.0
Very good
7,917 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,917 reviews
Delta
8.0
Very good
7,917 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,667 reviews
Delta
8.0
Very good
7,917 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,917 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Air Canada
7.0
Good
9,142 reviews
Delta
8.0
Very good
7,917 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
British Airways
6.6
Okay
6,767 reviews
Delta
8.0
Very good
7,917 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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), American Airlines ($295), and Delta ($298).

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

    On average you can expect to pay $685 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 $464.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for O'Hare Intl to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Oranjestad flights
Midway to Montego Bay flights
Midway to Punta Cana flights
O'Hare Intl to Nassau flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to George Town flights
O'Hare Intl to Castries flights
O'Hare Intl to Willemstad flights
Midway to Oranjestad flights
O'Hare Intl to Christiansted flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Puerto Plata flights
Midway to Nassau flights
O'Hare Intl to Providenciales flights
Midway to Saint Thomas Island flights
O'Hare Intl to Kingston flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Bridgetown flights
Midway to Providenciales flights
Midway to Santo Domingo flights
Midway to Santiago de los Caballeros flights
O'Hare Intl to St. John's flights
O'Hare Intl to Road Town flights
O'Hare Intl to Ponce flights
Midway to George Town flights
O'Hare Intl to Port of Spain flights
Midway to Simpson Bay flights
O'Hare Intl to Havana flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to Gregory Town flights
Midway to Kingston flights
O'Hare Intl to Freeport flights
O'Hare Intl to Culebra flights
O'Hare Intl to Basseterre flights
O'Hare Intl to The Valley flights
O'Hare Intl to Castries flights
O'Hare Intl to St. George's flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Kingstown flights
O'Hare Intl to Gustavia flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Georgetown flights
Midway to Castries flights
O'Hare Intl to Pointe-à-Pitre flights
O'Hare Intl to Port Royal flights

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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$463Average$668FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$468Average$662FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$503Average$705FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.