HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Grand Cayman

$136+ 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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from O'Hare Intl to Grand Cayman with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 17, 2025.

Round-trip from

$311
(Priceline)

One-way from

$136
(Air Canada)

Popular in

December

Cheapest in

October

Average price

$569
From Chicago O'Hare Intl to Grand Cayman
Search Deals
One-way flight from Chicago O'Hare Intl to Grand Cayman
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 17, 2025.

This Priceline deal was found by Cheapflights users on 9/15. 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 12/65:59 pmORD - GCM
1 stop16h 01mSpirit Airlines
Sat 12/1311:55 amGCM - ORD
1 stop10h 05mSpirit Airlines
Deal found 9/15$311
This Air Canada deal was found by Cheapflights users on 9/16. 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.
Thu 11/273:35 pmORD - GCM
2 stops19h 50mAir Canada
Tue 12/21:30 pmGCM - ORD
1 stop20h 43mAir Canada
Deal found 9/16$394
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 12/41:35 pmORD - GCM
1 stop21h 00mMultiple Airlines
Sun 12/1411:55 amGCM - ORD
1 stop8h 26mMultiple Airlines
Deal found 9/17$419
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 12/31:35 pmORD - GCM
1 stop21h 00mMultiple Airlines
Sun 12/1411:55 amGCM - ORD
1 stop12h 47mMultiple Airlines
Deal found 9/16$420
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 12/41:35 pmORD - GCM
1 stop21h 00mMultiple Airlines
Thu 12/1111:55 amGCM - ORD
1 stop10h 05mMultiple Airlines
Deal found 9/17$424
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Wed 12/31:35 pmORD - GCM
1 stop21h 00mMultiple Airlines
Thu 12/1111:55 amGCM - ORD
1 stop10h 05mMultiple Airlines
Deal found 9/17$425
This Booking.com deal was found by Cheapflights users on 9/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/26:05 pmORD - GCM
2 stops41h 20mAir Canada
Tue 12/91:30 pmGCM - ORD
2 stops24h 21mAir Canada
Deal found 9/16$426
This Air Canada deal was found by Cheapflights users on 9/16. 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.
Mon 12/89:10 pmORD - GCM
1 stop14h 15mAir Canada
Thu 12/111:30 pmGCM - ORD
1 stop24h 31mAir Canada
Deal found 9/16$430

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 September 17, 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 11/27

3:35 pm-12:25 pm

2 stops19h 50m

George Town Owen Roberts Intl

Tue 12/2

1:30 pm-9:13 am

1 stop20h 43m

$394

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/3

1:35 pm-11:35 am

1 stop21h 00m

George Town Owen Roberts Intl

Sun 12/14

11:55 am-7:21 pm

1 stop8h 26m

$420

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 12/4

1:35 pm-11:35 am

1 stop21h 00m

George Town Owen Roberts Intl

Sat 12/13

11:55 am-9:00 pm

1 stop10h 05m

$424

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 12/7

10:05 pm-9:15 pm

2 stops22h 10m

George Town Owen Roberts Intl

Sun 12/14

11:55 am-11:42 pm

1 stop12h 47m

$439

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 9/29

5:30 am-11:36 am

1 stop6h 06m

George Town Owen Roberts Intl

Fri 10/3

12:52 pm-9:25 pm

1 stop8h 33m

$446

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/3

6:05 am-12:35 pm

1 stop5h 30m

George Town Owen Roberts Intl

Wed 12/10

1:30 pm-9:50 pm

1 stop9h 20m

$446

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 9/29

5:30 am-11:36 am

1 stop6h 06m

George Town Owen Roberts Intl

Thu 10/2

12:52 pm-10:19 am

2 stops21h 27m

$450

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 12/2

8:49 am-4:30 pm

1 stop6h 41m

George Town Owen Roberts Intl

Tue 12/9

5:45 pm-12:15 am

1 stop7h 30m

$452

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 12/7

7:52 pm-12:35 pm

1 stop15h 43m

George Town Owen Roberts Intl

Thu 12/11

1:50 pm-12:01 am

1 stop11h 11m

$452

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 11/1

3:55 pm-12:25 pm

1 stop20h 30m

$136

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 17 results
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, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Grand Cayman (average of $467). Flying from Chicago O'Hare Intl Airport to Grand Cayman in March is currently the most expensive (average of $594). 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 September 17, 2025.

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 September 17, 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
8.0
Very good
7,961 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,926 reviews
Delta
8.0
Very good
7,961 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,961 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 $394, Air Canada can have you in Grand Cayman from Chicago O'Hare Intl Airport in 19h 50m. Chicago O'Hare Intl Airport and Grand Cayman are separated by a distance of 1613 mi.

  • 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 $634, our data indicates the cheapest price to be $527. The most popular route (Chicago O'Hare Intl - George Town Owen Roberts Intl), is priced around $319.

  • 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 $467). Flying from Chicago O'Hare Intl Airport to Grand Cayman in March is currently the most expensive (average of $594). 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.

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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$530Average$696FlexibilityNo cancel feeOn-time71%
DeltaCheapest$564Average$694FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$587Average$751FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.