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Grand Cayman

$202+ 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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Apr 8 — Apr 151
Tue 4/8
Tue 4/15
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 April 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$464
(Kiwi.com)

One-way from

$202
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$641
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. 8% potential increase in price ($62 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/2. 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 5/67:00 pmORD - GCM
1 stop21h 10mMultiple Airlines
Sat 5/108:50 amGCM - ORD
1 stop8h 51mMultiple Airlines
Deal found 4/2$464
This Air Canada deal was found by Cheapflights users on 4/1. 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 6/18:25 pmORD - GCM
1 stop15h 30mAir Canada
Thu 6/512:50 pmGCM - ORD
2 stops21h 02mAir Canada
Deal found 4/1$518
This American Airlines deal was found by Cheapflights users on 4/1. 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.
Wed 5/285:00 amORD - GCM
1 stop6h 10mAmerican Airlines
Tue 6/32:10 pmGCM - ORD
1 stop7h 15mAmerican Airlines
Deal found 4/1$610
This Delta deal was found by Cheapflights users on 4/2. 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.
Thu 5/155:30 amORD - GCM
1 stop5h 50mDelta
Thu 5/2212:35 pmGCM - ORD
1 stop8h 45mDelta
Deal found 4/2$635
This United Airlines deal was found by Cheapflights users on 4/2. 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 5/39:26 amORD - GCM
Nonstop4h 04mUnited Airlines
Sat 5/101:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
Deal found 4/2$645

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 April 3, 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

Tue 5/6

7:00 pm-4:10 pm

1 stop21h 10m

George Town Owen Roberts Intl

Sat 5/10

8:50 am-5:41 pm

1 stop8h 51m

$464

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 6/1

8:25 pm-11:55 am

1 stop15h 30m

George Town Owen Roberts Intl

Thu 6/5

12:50 pm-9:52 am

2 stops21h 02m

$518

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 5/28

5:00 am-11:10 am

1 stop6h 10m

George Town Owen Roberts Intl

Tue 6/3

2:10 pm-9:25 pm

1 stop7h 15m

$610

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 5/15

5:30 am-11:20 am

1 stop5h 50m

George Town Owen Roberts Intl

Thu 5/22

12:35 pm-9:20 pm

1 stop8h 45m

$635

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 5/3

9:26 am-1:30 pm

Nonstop4h 04m

George Town Owen Roberts Intl

Sat 5/10

1:45 pm-6:07 pm

Nonstop4h 22m

$645

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 5/10

9:19 am-4:05 pm

1 stop6h 46m

$202

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 5/5

6:00 am-11:50 am

1 stop5h 50m

$251

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 5/17

6:35 pm-11:20 am

1 stop16h 45m

$293

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 5/10

9:26 am-1:30 pm

Nonstop4h 04m

$313

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

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 April 3, 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 April 3, 2025.
Southwest
8.0
Very good
4,274 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,274 reviews
Southwest
8.0
Very good
4,274 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,897 reviews
Southwest
8.0
Very good
4,274 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,619 reviews
Southwest
8.0
Very good
4,274 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,274 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Air Canada
7.0
Good
9,028 reviews
Southwest
8.0
Very good
4,274 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $217. However, be on the lookout for offers from Air Canada and Delta, 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 $717, our data indicates the cheapest price to be $313. The most popular route (Chicago O'Hare Intl - George Town Owen Roberts Intl), is priced around $464.

  • 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

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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 April 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$463Average$628FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$468Average$660FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$504Average$702FlexibilityNo cancel feeOn-time69%

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