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Grand Cayman

$101+ 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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Mar 22 — Mar 291
Sun 3/22
Sun 3/29
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 20, 2026.

This Mytrip deal was found by Cheapflights users on 2/17. 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 Mytrip 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
Tue 3/311:30 am
GCM
-
ORD
3 stops31h 16m
Multiple Airlines
Deal found 2/17$451
This Air Canada deal was found by Cheapflights users on 2/16. 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 4/293:45 pm
ORD
-
GCM
2 stops19h 25m
Air Canada
Mon 5/412:25 pm
GCM
-
ORD
2 stops19h 33m
Air Canada
Deal found 2/16$454
This Expedia deal was found by Cheapflights users on 2/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:22 pm
ORD
-
GCM
2 stops41h 08m
Air Canada
Sat 5/3012:25 pm
GCM
-
ORD
2 stops19h 20m
Air Canada
Deal found 2/16$455
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 2/269:18 am
ORD
-
GCM
1 stop10h 57m
Multiple Airlines
Fri 3/65:05 pm
GCM
-
ORD
1 stop17h 34m
Multiple Airlines
Deal found 2/16$456
This Kiwi.com deal was found by Cheapflights users on 2/17. 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.
Thu 2/265:15 am
ORD
-
GCM
1 stop7h 28m
Multiple Airlines
Sun 3/12:49 pm
GCM
-
ORD
2 stops32h 50m
Multiple Airlines
Deal found 2/17$458
This Mytrip deal was found by Cheapflights users on 2/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:18 am
ORD
-
GCM
1 stop10h 57m
Multiple Airlines
Mon 3/97:00 am
GCM
-
ORD
3 stops34h 46m
Multiple Airlines
Deal found 2/17$459
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 3/1912:05 pm
ORD
-
GCM
1 stop29h 55m
Multiple Airlines
Wed 3/2511:30 am
GCM
-
ORD
1 stop20h 55m
Multiple Airlines
Deal found 2/16$460
This Mytrip deal was found by Cheapflights users on 2/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/136:01 pm
ORD
-
GCM
3 stops18h 19m
Spirit Airlines
Thu 3/191:52 pm
GCM
-
ORD
1 stop9h 25m
Spirit Airlines
Deal found 2/17$461
This Air Canada deal was found by Cheapflights users on 2/18. 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.
Sun 4/129:05 am
ORD
-
GCM
1 stop25h 10m
Air Canada
Fri 4/1711:10 am
GCM
-
ORD
1 stop8h 15m
Air Canada
Deal found 2/18$462
This Kiwi.com deal was found by Cheapflights users on 2/18. 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.
Fri 4/106:10 pm
ORD
-
GCM
1 stop18h 10m
Multiple Airlines
Fri 4/175:05 pm
GCM
-
ORD
2 stops21h 15m
Multiple Airlines
Deal found 2/18$463
This Mytrip deal was found by Cheapflights users on 2/19. 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 3/186:01 pm
ORD
-
GCM
3 stops18h 56m
Multiple Airlines
Sun 3/225:05 pm
GCM
-
ORD
1 stop15h 20m
Multiple Airlines
Deal found 2/19$464
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 5/145:01 am
ORD
-
GCM
2 stops16h 14m
Multiple Airlines
Sun 5/175:05 pm
GCM
-
ORD
1 stop6h 54m
Multiple Airlines
Deal found 2/18$465

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 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$454
(Air Canada)

One-way from

$101
(Expedia)

Popular in

December

Cheapest in

February

Average price

$527
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. 3% potential increase in price ($22 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
Search Deals

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 20, 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

Thu 3/19

12:05 pm-6:00 pm

1 stop29h 55m

George Town Owen Roberts Intl

Wed 3/25

11:30 am-8:25 am

1 stop20h 55m

$460

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

$471

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 5/10

6:34 pm-11:35 am

1 stop17h 01m

George Town Owen Roberts Intl

Sun 5/24

7:00 am-6:11 pm

1 stop11h 11m

$493

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 3/18

8:45 am-12:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Wed 3/25

1:50 pm-6:04 pm

Nonstop4h 14m

$501

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 3/22

8:45 am-12:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Thu 3/26

1:25 pm-11:13 pm

1 stop9h 48m

$511

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 3/31

4:51 pm-4:05 pm

1 stop23h 14m

George Town Owen Roberts Intl

Mon 4/6

7:00 am-9:50 am

1 stop26h 50m

$520

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 3/15

8:45 am-12:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Thu 3/19

1:50 pm-6:04 pm

Nonstop4h 14m

$521

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 4/5

5:48 am-12:30 pm

1 stop6h 42m

George Town Owen Roberts Intl

Thu 4/9

1:50 pm-6:13 pm

Nonstop4h 23m

$525

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 3/15

8:45 am-12:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Fri 3/20

1:25 pm-11:13 pm

1 stop9h 48m

$531

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 4/29

8:45 am-12:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Tue 5/5

1:35 pm-9:36 pm

1 stop8h 01m

$531

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/16

Showing 1-10 of 21 results
1
2
3

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 $661). 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 20, 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.

Weekly flight availability from Chicago O'Hare Intl Airport to Grand Cayman

Explore weekly flight availability from O'Hare Intl to Grand Cayman. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 20, 2026.

The most flights from ORD to zzLAW are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

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 20, 2026.
Get a feel of what it's like to fly with Delta, 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.
Delta
7.9
Good
8,215 reviews

Comfort

7.9

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,215 reviews
Delta
7.9
Good
8,215 reviews

Comfort

7.9

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,325 reviews
Delta
7.9
Good
8,215 reviews

Comfort

7.9

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,321 reviews
Delta
7.9
Good
8,215 reviews

Comfort

7.9

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 $501, Air Canada 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 $471, 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 $322.

  • 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 $661). 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 3 airlines flying from O'Hare Intl to Grand Cayman

Discover the top 3 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 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$174Average$609FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$341Average$612FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$438Average$674FlexibilityNo cancel feeOn-time71%

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