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Grand Cayman

$148+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
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 July 27, 2026.

This Travelocity deal was found by Cheapflights users on 7/25. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/235:35 pm
ORD
-
GCM
1 stop17h 50m
Air Canada
Sat 9/2610:40 am
GCM
-
ORD
1 stop28h 15m
Air Canada
Deal found 7/25$394
This Expedia deal was found by Cheapflights users on 7/25. 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.
Wed 9/168:45 am
ORD
-
GCM
2 stops26h 40m
Air Canada
Mon 9/2112:25 pm
GCM
-
ORD
2 stops26h 27m
Air Canada
Deal found 7/25$400
This Air Canada deal was found by Cheapflights users on 7/25. 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 9/165:53 pm
ORD
-
GCM
1 stop17h 32m
Air Canada
Sat 9/1910:40 am
GCM
-
ORD
1 stop22h 20m
Air Canada
Deal found 7/25$412
This Air Canada deal was found by Cheapflights users on 7/23. 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 9/66:21 pm
ORD
-
GCM
2 stops17h 04m
Air Canada
Thu 9/1012:25 pm
GCM
-
ORD
1 stop20h 35m
Air Canada
Deal found 7/23$439
This Flightnetwork deal was found by Cheapflights users on 7/26. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:45 pm
ORD
-
GCM
1 stop19h 40m
Multiple Airlines
Wed 9/167:00 am
GCM
-
ORD
2 stops36h 48m
Multiple Airlines
Deal found 7/26$446
This Air Canada deal was found by Cheapflights users on 7/26. 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.
Fri 10/238:40 pm
ORD
-
GCM
1 stop14h 50m
Air Canada
Sat 10/3112:10 pm
GCM
-
ORD
1 stop8h 03m
Air Canada
Deal found 7/26$455

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 July 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$394
(Travelocity)

One-way from

$148
(Expedia)

Popular in

July

Cheapest in

February

Average price

$986
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
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Highest demand for flights based on searches. 15% potential increase in price ($123 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($29 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 27, 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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 11/20

8:50 pm-12:10 pm

1 stop14h 20m

George Town Owen Roberts Intl

Thu 11/26

1:10 pm-8:00 am

2 stops19h 50m

$508

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 11/20

8:50 pm-12:10 pm

1 stop14h 20m

George Town Owen Roberts Intl

Wed 11/25

1:10 pm-8:00 am

2 stops19h 50m

$528

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 11/4

7:40 am-4:30 pm

1 stop7h 50m

George Town Owen Roberts Intl

Wed 11/11

5:45 pm-10:11 am

1 stop17h 26m

$631

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 10/28

5:29 pm-11:40 am

2 stops18h 11m

George Town Owen Roberts Intl

Tue 11/17

1:50 pm-11:59 pm

1 stop11h 09m

$636
Quickest round-trip

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 11/4

7:30 am-4:30 pm

1 stop8h 00m

George Town Owen Roberts Intl

Sat 11/7

2:55 pm-6:13 pm

Nonstop4h 18m

$671

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 12/5

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Mon 12/14

5:45 pm-7:47 am

1 stop15h 02m

$677

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 12/4

5:30 am-12:25 pm

1 stop5h 55m

George Town Owen Roberts Intl

Sun 12/6

1:50 pm-9:10 pm

1 stop8h 20m

$681

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 10/31

5:27 am-11:40 am

1 stop6h 13m

George Town Owen Roberts Intl

Mon 11/16

1:50 pm-8:48 pm

1 stop7h 58m

$681

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 10/11

5:30 am-12:30 pm

1 stop7h 00m

George Town Owen Roberts Intl

Sun 10/18

1:35 pm-12:23 am

1 stop10h 48m

$681

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 10/24

7:52 pm-12:15 pm

1 stop16h 23m

George Town Owen Roberts Intl

Sat 10/31

1:55 pm-6:13 pm

Nonstop4h 18m

$681

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

Showing 1-10 of 19 resultsSorted by cheapest first
1
2

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, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Grand Cayman (average of $530). Flying from Chicago O'Hare Intl Airport to Grand Cayman in November is currently the most expensive (average of $938). 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 July 27, 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 July 27, 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
10,041 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
United Airlines
7.4
Good
10,041 reviews
United Airlines
7.4
Good
10,041 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
American Airlines
7.1
Good
11,836 reviews
United Airlines
7.4
Good
10,041 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!

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 $631, Air Canada can have you in Grand Cayman from Chicago O'Hare Intl Airport in 7h 50m. 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 $774, our data indicates the cheapest price to be $631. The most popular route (Chicago O'Hare Intl - George Town Owen Roberts Intl), is priced around $458.

  • 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, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Grand Cayman (average of $530). Flying from Chicago O'Hare Intl Airport to Grand Cayman in November is currently the most expensive (average of $938). 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.

Complete your trip

Complete your trip to Grand Cayman by adding a car rental and/or hotel reservation to your travel itinerary.
George Town Owen Roberts Intl Airport car rentals
George Town car rentals

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 July 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$341Average$614FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$447Average$688FlexibilityNo cancel feeOn-time71%

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