HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Grand Cayman

$169+ 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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Jan 28 — Feb 41
Tue 1/28
Tue 2/4
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

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Grand Cayman (zzLAW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 23, 2025.

Round-trip from

$592
(Kiwi.com)

One-way from

$169
(Southwest)
From Chicago O'Hare Intl to Grand Cayman
Search Deals
One-way flight from Chicago O'Hare Intl to Grand Cayman
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 January 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
Tue 3/259:17 amORD - GCM
1 stop6h 53mMultiple Airlines
Thu 3/2711:30 amGCM - ORD
2 stops20h 14mMultiple Airlines
Deal found 1/21$592
This CheapOair deal was found by Cheapflights users on 1/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/119:07 pmORD - GCM
2 stops40h 53mAir Canada
Mon 3/173:00 pmGCM - ORD
2 stops23h 45mAir Canada
Deal found 1/22$597
This American Airlines deal was found by Cheapflights users on 1/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/236:58 pmORD - GCM
1 stop16h 02mAmerican Airlines
Thu 4/312:00 pmGCM - ORD
1 stop12h 20mAmerican Airlines
Deal found 1/23$600
This Delta deal was found by Cheapflights users on 1/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/265:45 amORD - GCM
1 stop5h 53mDelta
Wed 3/52:04 pmGCM - ORD
1 stop10h 45mDelta
Deal found 1/23$610
This United Airlines deal was found by Cheapflights users on 1/22. 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.
Sun 3/166:30 amORD - GCM
1 stop8h 55mUnited Airlines
Sun 3/231:50 pmGCM - ORD
Nonstop4h 16mUnited Airlines
Deal found 1/22$615
This Southwest deal was found by Cheapflights users on 1/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/77:10 pmORD - GCM
2 stops15h 05mSouthwest
Sat 3/151:10 pmGCM - ORD
2 stops20h 15mSouthwest
Deal found 1/22$800

Find flights from O'Hare Intl to Grand Cayman within your budget

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 January 23, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 3/25

9:17 am-4:10 pm

1 stop6h 53m

George Town Owen Roberts Intl

Thu 3/27

11:30 am-7:44 am

2 stops20h 14m

$592

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 3/11

9:07 pm-2:00 pm

2 stops40h 53m

George Town Owen Roberts Intl

Mon 3/17

3:00 pm-2:45 pm

2 stops23h 45m

$597

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 3/23

6:58 pm-11:00 am

1 stop16h 02m

George Town Owen Roberts Intl

Thu 4/3

12:00 pm-12:20 am

1 stop12h 20m

$600

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 2/26

5:45 am-12:38 pm

1 stop5h 53m

George Town Owen Roberts Intl

Tue 3/11

1:03 pm-11:56 pm

1 stop10h 53m

$610

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 3/16

6:30 am-3:25 pm

1 stop8h 55m

George Town Owen Roberts Intl

Sun 3/23

1:50 pm-6:06 pm

Nonstop4h 16m

$615

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 3/7

7:10 pm-11:15 am

2 stops15h 05m

George Town Owen Roberts Intl

Sat 3/15

1:10 pm-9:25 am

2 stops20h 15m

$800

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 4/22

6:00 am-11:50 am

1 stop5h 50m

$169

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 4/23

7:00 am-4:10 pm

1 stop9h 10m

$172

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 2/23

7:00 am-7:03 pm

1 stop11h 03m

$189

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 4/23

3:35 pm-12:25 pm

2 stops20h 50m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 14 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.

Travel insights for flights from O'Hare Intl to Grand Cayman

Get recent, data-driven insights about flights from O'Hare Intl to Grand Cayman including ideal travel times, pricing trends, and more.

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 January 23, 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 January 23, 2025.
See what other customers who have flown with Delta and American Airlines from Chicago to Grand Cayman have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,647 reviews

Food

7.2

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,647 reviews
Southwest
8.1
Very good
4,647 reviews

Food

7.2

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,512 reviews
Southwest
8.1
Very good
4,647 reviews

Food

7.2

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,975 reviews
Southwest
8.1
Very good
4,647 reviews

Food

7.2

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,647 reviews

Food

7.2

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

WestJet
7.2
Good
2,829 reviews
Southwest
8.1
Very good
4,647 reviews

Food

7.2

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Grand Cayman one-way?

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $169. However, be on the lookout for offers from Sun Country Air and Air Canada, 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 $575, 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 $453.

  • 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 January 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$373Average$532FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$436Average$633FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$461Average$697FlexibilityNo 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.