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Grand Cayman

$126+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Sep 9 — Sep 161
Wed 9/9
Wed 9/16
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 August 10, 2026.

This Trip.com deal was found by Cheapflights users on 8/9. 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.
Fri 9/115:35 pm -
1 stop16h 10m
Thu 9/1712:25 pm -
1 stop26h 25m
Deal found 8/9$329
This Expedia deal was found by Cheapflights users on 8/8. 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.
Fri 10/163:45 pm -
1 stop19h 45m
Sun 10/2512:10 pm -
1 stop8h 03m
Deal found 8/8$346

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 August 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$329
(Trip.com)

One-way from

$126
(Travelocity)

Popular in

July

Cheapest in

February

Average price

$686
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. 13% potential increase in price ($105 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 10, 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 Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Sun 1/17

5:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Fri 1/22

2:50 pm-6:04 pm

Nonstop4h 14m

$621

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Tue 1/26

5:45 pm-12:40 pm

2 stops17h 55m

George Town Owen Roberts Intl

Thu 1/28

2:05 pm-8:58 am

2 stops19h 53m

$636

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Tue 1/26

5:45 pm-12:40 pm

2 stops17h 55m

George Town Owen Roberts Intl

Tue 2/2

2:05 pm-12:37 pm

2 stops23h 32m

$636

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Wed 2/3

8:42 am-1:45 pm

Nonstop4h 03m

George Town Owen Roberts Intl

Sun 2/7

2:50 pm-6:04 pm

Nonstop4h 14m

$642

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Sun 12/13

6:00 am-4:30 pm

1 stop9h 30m

George Town Owen Roberts Intl

Sun 12/20

2:50 pm-6:04 pm

Nonstop4h 14m

$646

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Sat 1/23

5:30 am-2:15 pm

1 stop7h 45m

George Town Owen Roberts Intl

Tue 2/2

2:05 pm-12:37 pm

2 stops23h 32m

$661

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Fri 11/13

7:22 pm-12:25 pm

2 stops16h 03m

George Town Owen Roberts Intl

Tue 11/17

1:50 pm-7:46 am

2 stops18h 56m

$661

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Sat 11/14

11:29 am-12:25 pm

2 stops23h 56m

George Town Owen Roberts Intl

Wed 11/18

1:50 pm-11:59 pm

1 stop11h 09m

$661
Quickest round-trip

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Sat 1/30

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Sat 2/6

2:50 pm-6:04 pm

Nonstop4h 14m

$667

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Sat 11/14

8:42 am-1:45 pm

Nonstop4h 03m

George Town Owen Roberts Intl

Sat 11/21

2:55 pm-6:13 pm

Nonstop4h 18m

$667

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/5

Showing 1-10 of 18 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 $972). 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 August 10, 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.

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Grand Cayman?

Booking 1 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago O'Hare Intl Airport to Grand Cayman. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 August 10, 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
10,095 reviews

Entertainment

7.1

Boarding

7.7

Overall

7.4

Food

6.7

Comfort

7.3

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible
United Airlines
7.4
Good
10,095 reviews
United Airlines
7.4
Good
10,095 reviews

Entertainment

7.1

Boarding

7.7

Overall

7.4

Food

6.7

Comfort

7.3

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible
American Airlines
7.1
Good
11,897 reviews
United Airlines
7.4
Good
10,095 reviews

Entertainment

7.1

Boarding

7.7

Overall

7.4

Food

6.7

Comfort

7.3

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible

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 $621, United Airlines can have you in Grand Cayman from Chicago O'Hare Intl Airport in 7h 15m. 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 $641. The most popular route (Chicago O'Hare Intl - George Town Owen Roberts Intl), is priced around $465.

  • 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 $972). 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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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 August 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$341Average$613FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$438Average$687FlexibilityNo cancel feeOn-time71%

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