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Grand Cayman

$85+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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Cheap 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 November 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$272
(Priceline)

One-way from

$85
(Mytrip)

Popular in

December

Cheapest in

October

Average price

$804
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. 9% potential increase in price ($72 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find 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 November 4, 2025.

This Priceline deal was found by Cheapflights users on 11/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/67:10 amORD - GCM
1 stop8h 45mSpirit Airlines
Sat 12/135:56 pmGCM - ORD
1 stop7h 13mSpirit Airlines
Deal found 11/3$272
This Expedia deal was found by Cheapflights users on 11/3. 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.
Sun 12/145:00 amORD - GCM
1 stop7h 45mSpirit Airlines
Sun 12/212:40 pmGCM - ORD
1 stop10h 50mSpirit Airlines
Deal found 11/3$305
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/63:26 pmORD - GCM
1 stop21h 19mSpirit Airlines
Thu 12/112:40 pmGCM - ORD
1 stop10h 29mSpirit Airlines
Deal found 11/3$311
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/33:43 pmORD - GCM
1 stop21h 02mSpirit Airlines
Thu 12/112:40 pmGCM - ORD
1 stop10h 29mSpirit Airlines
Deal found 11/3$323
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/63:26 pmORD - GCM
1 stop21h 19mMultiple Airlines
Sun 12/142:40 pmGCM - ORD
1 stop9h 22mMultiple Airlines
Deal found 11/3$329
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Sat 11/298:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Sat 12/62:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 11/3$338
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/512:15 pmORD - GCM
2 stops27h 40mMultiple Airlines
Sat 12/135:56 pmGCM - ORD
1 stop7h 13mMultiple Airlines
Deal found 11/3$340
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/33:43 pmORD - GCM
1 stop21h 02mMultiple Airlines
Sun 12/142:40 pmGCM - ORD
1 stop9h 22mMultiple Airlines
Deal found 11/3$341
This American Airlines deal was found by Cheapflights users on 11/3. 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.
Sat 12/66:39 pmORD - GCM
1 stop16h 21mAmerican Airlines
Sat 12/134:09 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 11/3$342
This American Airlines deal was found by Cheapflights users on 11/4. 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.
Sat 11/297:11 amORD - GCM
1 stop6h 17mAmerican Airlines
Sat 12/61:01 pmGCM - ORD
1 stop8h 25mAmerican Airlines
Deal found 11/4$344
This Mytrip deal was found by Cheapflights users on 11/3. 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.
Sat 12/135:00 amORD - GCM
1 stop10h 55mMultiple Airlines
Wed 12/177:00 amGCM - ORD
1 stop12h 36mMultiple Airlines
Deal found 11/3$345
This American Airlines deal was found by Cheapflights users on 11/3. 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.
Sun 12/145:00 amORD - GCM
1 stop6h 00mAmerican Airlines
Sun 12/213:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 11/3$347

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 November 4, 2025.
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 2/5

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Mon 2/9

2:50 pm-6:04 pm

Nonstop4h 14m

$342

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 12/14

5:30 am-12:35 pm

1 stop6h 05m

George Town Owen Roberts Intl

Wed 12/24

1:52 pm-7:38 pm

1 stop6h 46m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 12/2

6:00 am-4:30 pm

1 stop9h 30m

George Town Owen Roberts Intl

Tue 12/9

5:45 pm-10:02 am

1 stop17h 17m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 2/6

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Tue 2/10

2:25 pm-10:59 pm

1 stop9h 34m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/10

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Sat 1/17

5:30 pm-11:39 pm

1 stop7h 09m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 2/1

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Sat 2/7

5:45 pm-12:28 am

1 stop7h 43m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/3

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Tue 1/13

2:25 pm-10:59 pm

1 stop9h 34m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 2/2

5:33 am-12:40 pm

1 stop6h 07m

George Town Owen Roberts Intl

Sun 2/8

2:05 pm-7:35 pm

1 stop6h 30m

$356

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 2/2

5:33 am-12:40 pm

1 stop6h 07m

George Town Owen Roberts Intl

Sat 2/7

3:25 pm-11:57 pm

1 stop9h 32m

$356

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 1/30

5:37 pm-11:19 am

1 stop16h 42m

George Town Owen Roberts Intl

Sat 2/7

3:25 pm-11:57 pm

1 stop9h 32m

$356

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 23 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, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Grand Cayman (average of $356). 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 November 4, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago O'Hare Intl Airport to Grand Cayman at noon. If you’re flexible enough to do this you can expect to save up to 47% on your trip compared to booking a flight in the morning.

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 November 4, 2025.
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
8,003 reviews

Food

7.3

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

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
8,003 reviews
Delta
7.9
Good
8,003 reviews

Food

7.3

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

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
9,002 reviews
Delta
7.9
Good
8,003 reviews

Food

7.3

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

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
11,040 reviews
Delta
7.9
Good
8,003 reviews

Food

7.3

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

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 $342, United 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. Most flights are nonstop.

  • 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 $641, our data indicates the cheapest price to be $341. The most popular route (Chicago O'Hare Intl - George Town Owen Roberts Intl), is priced around $329.

  • 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, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Grand Cayman (average of $356). 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 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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$434Average$721FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$488Average$707FlexibilityNo cancel feeOn-time71%
DeltaCheapest$564Average$694FlexibilityNo cancel feeOn-timeN/A

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