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O'Hare Intl

$264+ Cheap flights from the Cayman Islands to O'Hare Intl (ORD)

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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — ORD
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheap flight deals from Cayman Islands to O'Hare Intl

Keep the following information in mind while searching for Cayman Islands to O'Hare Intl flight deals. Data was last updated July 30, 2025.

Round-trip from

$447
(Air Canada)

One-way from

$274
(Delta)

Good round-trip deal

$660 or less

Good one-way deal

$380 or less
From Cayman Islands to Chicago O'Hare Intl
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One-way flight from Cayman Islands to Chicago O'Hare Intl
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Price to beat on a round-trip flight from Cayman Islands to Chicago O'Hare Intl.
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Price to beat on a one-way flight from Cayman Islands to Chicago O'Hare Intl.
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Find flight deals from Cayman Islands to O'Hare Intl

Cheapest flights from Cayman Islands to O'Hare Intl
Explore the most affordable flight options available from Cayman Islands to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2025.

This Southwest deal was found by Cheapflights users on 7/30. 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 11/141:30 pmGCM - ORD
1 stop9h 20mSouthwest
Sun 11/166:05 amORD - GCM
1 stop5h 30mSouthwest
Deal found 7/30$410
This Air Canada deal was found by Cheapflights users on 7/29. 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 10/1612:50 pmGCM - ORD
2 stops45h 01mAir Canada
Sat 10/186:00 pmORD - GCM
2 stops41h 55mAir Canada
Deal found 7/29$447
This Delta deal was found by Cheapflights users on 7/29. 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.
Fri 9/1212:52 pmGCM - ORD
1 stop11h 02mDelta
Fri 9/195:30 amORD - GCM
1 stop6h 06mDelta
Deal found 7/29$468
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Fri 9/1212:25 pmGCM - ORD
2 stops11h 23mAmerican Airlines
Fri 9/198:30 pmORD - GCM
2 stops14h 40mAmerican Airlines
Deal found 7/29$481
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Mon 8/184:45 pmGCM - ORD
1 stop16h 37mMultiple Airlines
Thu 8/2110:27 amORD - GCM
1 stop10h 53mMultiple Airlines
Deal found 7/29$482

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cayman Islands to O'Hare Intl 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 July 30, 2025.
Use the filters below to find and compare flights from the Cayman Islands to Chicago O'Hare Intl Airport that are best for you.

Fly from

Cayman Islands

Fly to

O'Hare Intl

Route

Depart

Return

Price

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 11/14

1:30 pm-9:50 pm

1 stop9h 20m

Chicago O'Hare Intl

Sun 11/16

6:05 am-12:35 pm

1 stop5h 30m

$410

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 10/16

12:50 pm-9:51 am

2 stops45h 01m

Chicago O'Hare Intl

Sat 10/18

6:00 pm-11:55 am

2 stops41h 55m

$447

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 9/12

12:52 pm-11:54 pm

1 stop11h 02m

Chicago O'Hare Intl

Fri 9/19

5:30 am-11:36 am

1 stop6h 06m

$468

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 9/12

12:25 pm-11:48 pm

2 stops11h 23m

Chicago O'Hare Intl

Fri 9/19

8:30 pm-11:10 am

2 stops14h 40m

$481

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 8/18

4:45 pm-9:22 am

1 stop16h 37m

Chicago O'Hare Intl

Thu 8/21

10:27 am-9:20 pm

1 stop10h 53m

$482

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 1/14

1:50 pm-9:50 pm

1 stop9h 00m

$264

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 8/28

12:50 pm-10:37 pm

1 stop9h 47m

$274

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 10/31

12:30 pm-3:11 pm

1 stop26h 41m

$275

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 8/27

2:10 pm-10:41 pm

1 stop8h 31m

$278

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 8/29

4:45 pm-9:22 am

1 stop16h 37m

$291

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 12 results
1
2

Best time to book a flight from Cayman Islands to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Cayman Islands 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 the Cayman Islands to Chicago O'Hare Intl Airport

What is the cheapest time of day to fly from KY to ORD?

Find hourly flight availability from Cayman Islands to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 30, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Cayman Islands to Chicago O'Hare Intl Airport as you normally would.

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated July 30, 2025.
Read through reviews of airlines operating flights from the Cayman Islands to Chicago O'Hare Intl Airport, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
United Airlines
7.4
Good
8,896 reviews
Delta
8.0
Very good
7,980 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Air Canada
7.1
Good
9,837 reviews
Delta
8.0
Very good
7,980 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.

Related info for your journey

Find useful and relevant information for your journey from Cayman Islands to O'Hare Intl. 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 Cayman Islands to Chicago O'Hare Intl Airport one-way?

    One-way options have recently been found by users for as low as $274 on Delta. Other airlines that offer cheap prices include Air Canada from $277 and American Airlines from $278 one-way.

  • What are the cheapest flights from Cayman Islands to Chicago O'Hare Intl Airport?

    On average you can expect to pay $924 for a flight from Cayman Islands to Chicago O'Hare Intl Airport. The cheapest flight overall is $295 while the most popular route, (George Town Owen Roberts Intl - Chicago O'Hare Intl) is currently priced at $468.

  • Can I find deals for flights from Cayman Islands to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Cayman Islands to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Cayman Islands to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Cayman Islands to O'Hare Intl.

  • Can I find deals for business class flights from Cayman Islands to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Cayman Islands to O'Hare Intl 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 Cayman Islands to Chicago O'Hare Intl Airport?

    Currently, August is the cheapest month in which you can book a flight from Cayman Islands to Chicago O'Hare Intl Airport (average of $245). Flying from Cayman Islands to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Beloit
Hoffman Estates
Skokie
Naperville
Des Plaines
Elgin
Arlington Heights
Elk Grove Village
Racine
Rockford
Tinley Park
Orland Park
Merrillville
Downers Grove
Evanston
Lake Geneva
Gurnee
Joliet

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