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Grand Cayman

$59+ Cheap flights from O'Hare Intl (ORD) to Grand Cayman

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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Mar 4 — Mar 111
Wed 3/4
Wed 3/11
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Grand Cayman

Cheapest flights from O'Hare Intl to Grand Cayman
Explore the most affordable flight options available from O'Hare Intl to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 2, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Thu 2/265:15 am
ORD
-
GCM
1 stop7h 28m
Multiple Airlines
Sun 3/12:49 pm
GCM
-
ORD
2 stops27h 34m
Multiple Airlines
Deal found 2/1$357
This FlightHub deal was found by Cheapflights users on 1/31. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:05 am
ORD
-
GCM
1 stop5h 38m
Spirit Airlines
Sat 5/91:40 pm
GCM
-
ORD
1 stop10h 01m
Spirit Airlines
Deal found 1/31$362
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/225:15 am
ORD
-
GCM
1 stop7h 28m
Multiple Airlines
Fri 2/274:45 pm
GCM
-
ORD
2 stops19h 06m
Multiple Airlines
Deal found 1/30$363
This FlightHub deal was found by Cheapflights users on 2/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/75:15 am
ORD
-
GCM
1 stop7h 23m
Spirit Airlines
Thu 2/122:49 pm
GCM
-
ORD
1 stop9h 58m
Spirit Airlines
Deal found 2/2$364
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Mon 3/211:33 am
ORD
-
GCM
1 stop27h 32m
Multiple Airlines
Fri 3/67:00 am
GCM
-
ORD
1 stop9h 38m
Multiple Airlines
Deal found 2/1$365
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 3/148:58 pm
ORD
-
GCM
2 stops15h 59m
Multiple Airlines
Tue 3/1711:30 am
GCM
-
ORD
1 stop7h 01m
Multiple Airlines
Deal found 1/31$366
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Wed 2/258:16 pm
ORD
-
GCM
1 stop16h 27m
Multiple Airlines
Sun 3/12:49 pm
GCM
-
ORD
2 stops21h 02m
Multiple Airlines
Deal found 2/1$370
This Mytrip deal was found by Cheapflights users on 1/31. 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 3/412:44 pm
ORD
-
GCM
3 stops23h 59m
Spirit Airlines
Sun 3/81:49 pm
GCM
-
ORD
1 stop9h 58m
Spirit Airlines
Deal found 1/31$371
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Thu 2/265:15 am
ORD
-
GCM
1 stop7h 28m
Multiple Airlines
Mon 3/24:45 pm
GCM
-
ORD
2 stops25h 07m
Multiple Airlines
Deal found 2/1$372
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Wed 5/61:27 pm
ORD
-
GCM
1 stop23h 16m
Multiple Airlines
Tue 5/1211:30 am
GCM
-
ORD
1 stop6h 45m
Multiple Airlines
Deal found 2/1$373
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Thu 2/265:15 am
ORD
-
GCM
1 stop7h 28m
Multiple Airlines
Tue 3/311:30 am
GCM
-
ORD
2 stops30h 22m
Multiple Airlines
Deal found 1/31$374
This Air Canada deal was found by Cheapflights users on 2/1. 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.
Wed 6/172:15 pm
ORD
-
GCM
1 stop21h 15m
Air Canada
Sat 6/2712:25 pm
GCM
-
ORD
1 stop26h 30m
Air Canada
Deal found 2/1$375

Find flight deals from O'Hare Intl to Grand Cayman

Keep the following information in mind while searching for O'Hare Intl to Grand Cayman flight deals. Data was last updated February 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$357
(Kiwi.com)

One-way from

$59
(Expedia)

Popular in

December

Cheapest in

October

Average price

$570
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 Grand Cayman
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One-way flight from Chicago O'Hare Intl to Grand Cayman
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in February 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Grand Cayman 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 February 2, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Grand Cayman that are best for you.

Fly from

O'Hare Intl

Fly to

Grand Cayman

Route

Depart

Return

Price

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 3/1

6:04 pm-12:25 pm

2 stops17h 21m

George Town Owen Roberts Intl

Sun 3/8

1:49 pm-9:13 pm

1 stop7h 24m

$377

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 3/18

7:18 pm-12:57 pm

2 stops17h 39m

George Town Owen Roberts Intl

Sun 3/22

5:05 pm-8:25 am

1 stop15h 20m

$379

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 3/20

7:31 pm-12:20 pm

2 stops16h 49m

George Town Owen Roberts Intl

Tue 3/31

11:30 am-9:50 am

1 stop22h 20m

$444

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 2/12

5:15 am-1:43 pm

1 stop7h 28m

George Town Owen Roberts Intl

Sun 2/15

2:49 pm-11:47 pm

1 stop9h 58m

$445

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 2/16

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Fri 2/20

2:50 pm-6:04 pm

Nonstop4h 14m

$455

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 2/22

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Fri 2/27

2:50 pm-6:04 pm

Nonstop4h 14m

$455

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 2/16

9:18 am-9:15 pm

1 stop10h 57m

George Town Owen Roberts Intl

Fri 2/20

7:00 am-11:47 pm

3 stops17h 47m

$484

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 3/26

8:40 pm-11:25 am

1 stop14h 45m

George Town Owen Roberts Intl

Thu 4/2

11:55 am-9:10 am

1 stop21h 15m

$486

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 2/26

8:40 pm-12:25 pm

1 stop14h 45m

George Town Owen Roberts Intl

Tue 3/3

1:30 pm-9:13 am

1 stop20h 43m

$491

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 4/1

6:21 pm-10:55 am

2 stops16h 34m

George Town Owen Roberts Intl

Sun 4/5

11:55 am-9:10 am

1 stop21h 15m

$491

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

Showing 1-10 of 21 results
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Best time to book a flight from O'Hare Intl to Grand Cayman

Have a flexible travel schedule? Discover the best time to fly to Grand Cayman 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 Grand Cayman

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Grand Cayman?

Currently, December is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Grand Cayman (average of $322). Flying from Chicago O'Hare Intl Airport to Grand Cayman in September is currently the most expensive (average of $650). 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 LAW?

Find hourly flight availability from O'Hare Intl to Grand Cayman. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 2, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago O'Hare Intl Airport to Grand Cayman as you normally would.

Reviews of airlines servicing Grand Cayman

Get insights into the airlines that provide service to Grand Cayman. 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 Grand Cayman. Reviews last updated February 2, 2026.
Get a feel of what it's like to fly with United Airlines and American Airlines from Chicago O'Hare Intl Airport to Grand Cayman by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,229 reviews

Food

6.6

Overall

7.4

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,229 reviews
United Airlines
7.4
Good
9,229 reviews

Food

6.6

Overall

7.4

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.2
Good
11,212 reviews
United Airlines
7.4
Good
9,229 reviews

Food

6.6

Overall

7.4

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Grand Cayman. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago O'Hare Intl Airport to Grand Cayman?

    For as low as $455, Spirit Airlines can have you in Grand Cayman from Chicago O'Hare Intl Airport in 4h. Chicago O'Hare Intl Airport and Grand Cayman are separated by a distance of 1613 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Grand Cayman one-way?

    The cheapest airline one-way is Air Canada, with whom users have recently found tickets for as low as $137. However, be on the lookout for offers from American Airlines and United Airlines, as they are both options that can get you from Chicago O'Hare Intl Airport to Grand Cayman for a low price.

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

    Looking for the cheapest flight from Chicago O'Hare Intl Airport to Grand Cayman? While on average our users pay $449, our data indicates the cheapest price to be $288. The most popular route (Chicago O'Hare Intl - George Town Owen Roberts Intl), is priced around $276.

  • Can I find deals for flights from O'Hare Intl to Grand Cayman that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Grand Cayman flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Grand Cayman?

    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 Grand Cayman.

  • Can I find deals for business class flights from O'Hare Intl to Grand Cayman?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Grand Cayman 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 Grand Cayman?

    Currently, December is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Grand Cayman (average of $322). Flying from Chicago O'Hare Intl Airport to Grand Cayman in September is currently the most expensive (average of $650). 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 Grand Cayman

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to George Town flights
Midway to George Town flights
O'Hare Intl to Cayman Brac flights

Top 2 airlines flying from O'Hare Intl to Grand Cayman

Discover the top 2 airlines that operate flights from O'Hare Intl to Grand Cayman. 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 February 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$341Average$622FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$438Average$700FlexibilityNo cancel feeOn-time71%

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