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O'Hare Intl

$175+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — ORD
dic. 3 — dic. 101
mié. 12/3
mié. 12/10
1 adult, Economy
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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 noviembre 3, 2025.

This United Airlines deal was found by Cheapflights users on 11/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/182:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
jue. 12/258:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Deal found 11/3$338
This United Airlines deal was found by Cheapflights users on 11/2. 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.
mar. 12/25:45 pmGCM - ORD
1 stop28h 31mUnited Airlines
mar. 12/98:49 amORD - GCM
1 stop6h 41mUnited Airlines
Deal found 11/2$343
This United Airlines deal was found by Cheapflights users on 11/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/135:45 pmGCM - ORD
1 stop27h 11mUnited Airlines
dom. 11/168:50 amORD - GCM
1 stop6h 40mUnited Airlines
Deal found 11/1$375
This American Airlines deal was found by Cheapflights users on 11/1. 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.
jue. 11/131:20 pmGCM - ORD
2 stops9h 03mAmerican Airlines
dom. 11/165:00 amORD - GCM
1 stop5h 57mAmerican Airlines
Deal found 11/1$388
This United Airlines deal was found by Cheapflights users on 11/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/135:45 pmGCM - ORD
1 stop27h 11mUnited Airlines
lun. 11/176:00 amORD - GCM
1 stop9h 30mUnited Airlines
Deal found 11/1$397
This American Airlines deal was found by Cheapflights users on 11/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/29:00 amGCM - ORD
2 stops9h 52mAmerican Airlines
mar. 12/98:55 pmORD - GCM
2 stops14h 10mAmerican Airlines
Deal found 11/2$407
This American Airlines deal was found by Cheapflights users on 11/1. 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.
jue. 11/131:20 pmGCM - ORD
2 stops9h 03mAmerican Airlines
lun. 11/178:10 amORD - GCM
1 stop5h 36mAmerican Airlines
Deal found 11/1$411
This United Airlines deal was found by Cheapflights users on 11/2. 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.
mié. 12/242:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
dom. 12/289:23 pmORD - GCM
1 stop17h 37mUnited Airlines
Deal found 11/2$447
This Mytrip deal was found by Cheapflights users on 11/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/182:40 pmGCM - ORD
2 stops18h 51mSpirit Airlines
jue. 12/255:00 amORD - GCM
1 stop7h 45mSpirit Airlines
Deal found 11/3$472
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/1911:30 amGCM - ORD
1 stop24h 05mMultiple Airlines
dom. 11/2311:40 amORD - GCM
1 stop22h 55mMultiple Airlines
Deal found 11/1$483

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 noviembre 3, 2025.

Round-trip from

$338
(United Airlines)

One-way from

$175
(Flightnetwork)

Popular in

March

Cheapest in

October

Average price

$736

Good round-trip deal

$390 or less

Good one-way deal

$387 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. 32% potential increase in price ($320 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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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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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 noviembre 3, 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

jue. 12/18

2:50 pm-6:04 pm

Nonstop4h 14m

Chicago O'Hare Intl

jue. 12/25

8:45 am-1:45 pm

Nonstop4h 00m

$338

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

jue. 12/18

1:50 pm-10:43 pm

1 stop9h 53m

Chicago O'Hare Intl

jue. 12/25

5:30 am-2:27 pm

1 stop7h 57m

$343

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mar. 12/2

5:45 pm-9:16 pm

1 stop28h 31m

Chicago O'Hare Intl

mar. 12/9

8:49 am-4:30 pm

1 stop6h 41m

$343

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

jue. 11/13

5:45 pm-7:56 pm

1 stop27h 11m

Chicago O'Hare Intl

dom. 11/16

8:50 am-4:30 pm

1 stop6h 40m

$375

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

jue. 11/13

1:20 pm-9:23 pm

2 stops9h 03m

Chicago O'Hare Intl

dom. 11/16

5:00 am-11:57 am

1 stop5h 57m

$388

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

jue. 11/13

5:45 pm-7:56 pm

1 stop27h 11m

Chicago O'Hare Intl

lun. 11/17

6:00 am-4:30 pm

1 stop9h 30m

$397

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mar. 12/2

9:00 am-5:52 pm

2 stops9h 52m

Chicago O'Hare Intl

mar. 12/9

8:55 pm-12:05 pm

2 stops14h 10m

$407

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mié. 12/24

2:50 pm-6:04 pm

Nonstop4h 14m

Chicago O'Hare Intl

dom. 12/28

9:23 pm-4:00 pm

1 stop17h 37m

$447

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

jue. 12/18

2:40 pm-8:31 am

2 stops18h 51m

Chicago O'Hare Intl

jue. 12/25

5:00 am-1:45 pm

1 stop7h 45m

$472

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mié. 11/19

11:30 am-10:35 am

1 stop24h 05m

Chicago O'Hare Intl

dom. 11/23

11:40 am-11:35 am

1 stop22h 55m

$483

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

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 noviembre 3, 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.

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?

    United Airlines, Delta, and American Airlines can get you from Cayman Islands to Chicago O'Hare Intl Airport in just under 4h 14m. Your travel time can differ by up to 5h 39m. The distance from Cayman Islands to Chicago O'Hare Intl Airport is about 1613 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    On average you can expect to pay $506 for a flight from Cayman Islands to Chicago O'Hare Intl Airport. The cheapest flight overall is $365 while the most popular route, (George Town Owen Roberts Intl - Chicago O'Hare Intl) is currently priced at $343.

  • 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
Skokie
Des Plaines
Gurnee
Hoffman Estates
Beloit
Elgin
Oak Brook
Elk Grove Village
Naperville
Racine
Downers Grove
Rockford
Orland Park
Merrillville
Bridgeview
Warrenville
Waukegan
Aurora

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Alternative routes for Cayman Islands to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
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