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Grand Cayman

$88+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
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 January 6, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$323
(Kiwi.com)

One-way from

$88
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$575
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. 5% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 6, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/184:43 pmORD - GCM
1 stop20h 00mSpirit Airlines
Sun 2/222:49 pmGCM - ORD
2 stops18h 05mSpirit Airlines
Deal found 1/4$323
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 2/184:43 pmORD - GCM
1 stop20h 00mMultiple Airlines
Mon 2/234:45 pmGCM - ORD
1 stop17h 54mMultiple Airlines
Deal found 1/5$325
This Travelocity deal was found by Cheapflights users on 1/3. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/175:15 amORD - GCM
1 stop7h 23mMultiple Airlines
Tue 1/201:30 pmGCM - ORD
1 stop30h 20mMultiple Airlines
Deal found 1/3$326
This Mytrip deal was found by Cheapflights users on 1/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/245:15 amORD - GCM
1 stop7h 23mMultiple Airlines
Wed 1/285:10 pmGCM - ORD
1 stop17h 02mMultiple Airlines
Deal found 1/4$329
This Kiwi.com deal was found by Cheapflights users on 1/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/315:15 amORD - GCM
1 stop7h 23mSpirit Airlines
Sat 2/72:34 pmGCM - ORD
2 stops19h 38mSpirit Airlines
Deal found 1/4$330
This Priceline deal was found by Cheapflights users on 1/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/155:15 amORD - GCM
1 stop7h 38mSpirit Airlines
Sun 1/182:49 pmGCM - ORD
1 stop7h 14mSpirit Airlines
Deal found 1/4$333
This Orbitz deal was found by Cheapflights users on 1/4. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/68:43 pmORD - GCM
1 stop15h 55mMultiple Airlines
Mon 2/91:30 pmGCM - ORD
1 stop21h 35mMultiple Airlines
Deal found 1/4$336
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 2/68:43 pmORD - GCM
1 stop15h 55mMultiple Airlines
Fri 2/137:00 amGCM - ORD
1 stop9h 18mMultiple Airlines
Deal found 1/6$338
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 2/195:15 amORD - GCM
1 stop7h 28mSpirit Airlines
Sun 2/222:49 pmGCM - ORD
1 stop21h 33mSpirit Airlines
Deal found 1/5$343
This Mytrip deal was found by Cheapflights users on 1/5. 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.
Thu 1/225:15 amORD - GCM
1 stop7h 38mMultiple Airlines
Sat 1/312:34 pmGCM - ORD
3 stops24h 31mMultiple Airlines
Deal found 1/5$344
This Kiwi.com deal was found by Cheapflights users on 1/3. 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 2/116:02 pmORD - GCM
2 stops18h 41mMultiple Airlines
Thu 2/192:49 pmGCM - ORD
1 stop9h 35mMultiple Airlines
Deal found 1/3$345

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 January 6, 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

O'Hare Intl

Fly to

Grand Cayman

Route

Depart

Return

Price

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 1/25

5:15 am-1:53 pm

1 stop7h 38m

George Town Owen Roberts Intl

Wed 1/28

11:30 am-8:18 am

1 stop21h 48m

$326

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 1/18

3:35 pm-12:25 pm

2 stops19h 50m

George Town Owen Roberts Intl

Fri 1/23

1:30 pm-8:05 am

2 stops19h 35m

$422

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 2/17

5:25 am-12:29 pm

1 stop6h 04m

George Town Owen Roberts Intl

Tue 2/24

1:54 pm-11:56 pm

1 stop11h 02m

$453

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 3/23

6:04 pm-11:25 am

2 stops17h 21m

George Town Owen Roberts Intl

Thu 3/26

12:30 pm-10:04 pm

1 stop9h 34m

$453

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 2/10

5:30 am-12:40 pm

1 stop6h 10m

George Town Owen Roberts Intl

Wed 2/18

1:54 pm-7:19 pm

1 stop6h 25m

$453

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 2/17

5:25 am-12:29 pm

1 stop6h 04m

George Town Owen Roberts Intl

Fri 2/20

1:54 pm-9:01 pm

1 stop8h 07m

$453

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 2/18

2:05 pm-12:29 pm

2 stops21h 24m

George Town Owen Roberts Intl

Fri 2/20

1:54 pm-9:01 pm

1 stop8h 07m

$458

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/31

12:00 pm-1:53 pm

1 stop24h 53m

$92

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 2/7

5:32 pm-1:53 pm

1 stop19h 21m

$95

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 2/1

5:15 am-1:53 pm

1 stop7h 38m

$95

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/3

Showing 1-10 of 18 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 $321). 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 January 6, 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.

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 6, 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
9,132 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
United Airlines
7.4
Good
9,132 reviews
United Airlines
7.4
Good
9,132 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
American Airlines
7.2
Good
11,084 reviews
United Airlines
7.4
Good
9,132 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.

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 $453, Air Canada can have you in Grand Cayman from Chicago O'Hare Intl Airport in 6h 04m. 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 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 $507, 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 $217.

  • 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 $321). 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 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 January 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$341Average$632FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$448Average$738FlexibilityNo cancel feeOn-time71%

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