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O'Hare Intl

$193+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — ORD
Mar 13 — Mar 201
Fri 3/13
Fri 3/20
1 adult, Economy
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Cheap 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 February 11, 2026.

This Mytrip deal was found by Cheapflights users on 2/9. 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 2/122:49 pm
GCM
-
ORD
1 stop9h 58m
Multiple Airlines
Mon 2/233:55 pm
ORD
-
GCM
1 stop19h 30m
Multiple Airlines
Deal found 2/9$301
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/94:45 pm
GCM
-
ORD
1 stop16h 54m
Multiple Airlines
Wed 3/116:36 pm
ORD
-
GCM
1 stop18h 21m
Multiple Airlines
Deal found 2/10$331
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/97:00 am
GCM
-
ORD
1 stop26h 39m
Multiple Airlines
Thu 3/125:05 am
ORD
-
GCM
1 stop7h 52m
Multiple Airlines
Deal found 2/10$354
This Travelocity deal was found by Cheapflights users on 2/7. 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.
Thu 5/281:40 pm
GCM
-
ORD
1 stop10h 01m
Multiple Airlines
Sun 5/316:23 pm
ORD
-
GCM
2 stops17h 07m
Multiple Airlines
Deal found 2/7$371
This Mytrip deal was found by Cheapflights users on 2/9. 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 3/261:52 pm
GCM
-
ORD
1 stop9h 25m
Spirit Airlines
Thu 4/25:05 am
ORD
-
GCM
1 stop7h 52m
Spirit Airlines
Deal found 2/9$382
This Mytrip deal was found by Cheapflights users on 2/8. 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.
Tue 2/101:30 pm
GCM
-
ORD
2 stops19h 35m
Multiple Airlines
Thu 2/195:15 am
ORD
-
GCM
1 stop7h 28m
Multiple Airlines
Deal found 2/8$385
This Mytrip deal was found by Cheapflights users on 2/8. 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.
Mon 4/611:25 am
GCM
-
ORD
1 stop25h 40m
Multiple Airlines
Fri 4/106:01 pm
ORD
-
GCM
2 stops18h 19m
Multiple Airlines
Deal found 2/8$393
This Booking.com deal was found by Cheapflights users on 2/8. 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.
Mon 2/91:30 pm
GCM
-
ORD
1 stop29h 18m
Air Canada
Thu 2/198:00 am
ORD
-
GCM
1 stop27h 25m
Air Canada
Deal found 2/8$396

Find 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 February 11, 2026.

Round-trip from

$331
(Kiwi.com)

One-way from

$193
(Kiwi.com)

Popular in

April

Cheapest in

November

Average price

$454

Good round-trip deal

$276 or less

Good one-way deal

$220 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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Highest demand for flights based on searches. 28% potential increase in price ($231 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($43 potential savings vs. average RT price).
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Average for round-trip flights in February 2026
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Price to beat on a round-trip flight from Cayman Islands to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Cayman Islands to Chicago O'Hare Intl.
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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 February 11, 2026.
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

Mon 3/9

4:45 pm-9:39 am

1 stop16h 54m

Chicago O'Hare Intl

Wed 3/11

6:36 pm-12:57 pm

1 stop18h 21m

$331

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 5/28

1:40 pm-11:41 pm

1 stop10h 01m

Chicago O'Hare Intl

Sun 5/31

6:23 pm-11:30 am

2 stops17h 07m

$371

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 4/10

11:10 am-7:25 pm

1 stop8h 15m

Chicago O'Hare Intl

Sat 4/11

6:40 pm-10:55 am

1 stop16h 15m

$382

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 3/9

7:00 am-8:23 am

2 stops25h 23m

Chicago O'Hare Intl

Thu 3/12

5:05 am-12:57 pm

1 stop7h 52m

$391

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 4/6

11:25 am-1:05 pm

1 stop25h 40m

Chicago O'Hare Intl

Fri 4/10

6:01 pm-12:20 pm

2 stops18h 19m

$393

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 3/26

1:52 pm-12:17 am

2 stops10h 25m

Chicago O'Hare Intl

Thu 4/2

6:40 am-9:15 pm

1 stop14h 35m

$396

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 2/23

4:45 pm-4:52 pm

2 stops25h 07m

Chicago O'Hare Intl

Thu 2/26

5:15 am-1:43 pm

1 stop7h 28m

$418

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 5/28

12:25 pm-7:35 am

2 stops19h 10m

Chicago O'Hare Intl

Sun 5/31

6:23 pm-11:30 am

2 stops17h 07m

$433

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 3/26

12:30 pm-8:00 am

2 stops19h 30m

Chicago O'Hare Intl

Thu 4/2

3:45 pm-10:10 am

2 stops18h 25m

$456

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 5/7

1:40 pm-9:17 pm

1 stop7h 37m

$193

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/8

Showing 1-10 of 18 results
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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 February 11, 2026.

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.

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.

  • How long is the flight from Cayman Islands to Chicago O'Hare Intl Airport?

    Air Canada can get you from Cayman Islands to Chicago O'Hare Intl Airport in just under 8h 15m. Your travel time can differ by up to . The distance from Cayman Islands to Chicago O'Hare Intl Airport is about 1613 mi.

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

    On average you can expect to pay $405 for a flight from Cayman Islands to Chicago O'Hare Intl Airport. The cheapest flight overall is $212 while the most popular route, (George Town Owen Roberts Intl - Chicago O'Hare Intl) is currently priced at $301.

  • 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.

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
Naperville
Gurnee
Elgin
Hoffman Estates
Beloit
Delavan
Oak Brook
Des Plaines
Downers Grove
Elk Grove Village
Skokie
Libertyville
Lake Geneva
Waukegan
Bridgeview
Kenosha
Warrenville
Aurora

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