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O'Hare Intl

$208+ 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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — ORD
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
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 septiembre 15, 2025.

Round-trip from

$471
(American Airlines)

One-way from

$208
(Priceline)

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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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 septiembre 15, 2025.

This United Airlines deal was found by Cheapflights users on 9/13. 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. 10/284:45 pmGCM - ORD
1 stop17h 17mUnited Airlines
mar. 11/47:10 amORD - GCM
1 stop8h 20mUnited Airlines
Deal found 9/13$440
This American Airlines deal was found by Cheapflights users on 9/13. 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.
sáb. 11/112:10 pmGCM - ORD
1 stop10h 25mAmerican Airlines
sáb. 11/84:05 pmORD - GCM
1 stop18h 52mAmerican Airlines
Deal found 9/13$478
This Trip.com deal was found by Cheapflights users on 9/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/11:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
sáb. 11/88:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Deal found 9/13$495
This United Airlines deal was found by Cheapflights users on 9/13. 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
mié. 12/315:49 amORD - GCM
1 stop9h 11mUnited Airlines
Deal found 9/13$505
This Delta deal was found by Cheapflights users on 9/13. 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.
mié. 12/241:52 pmGCM - ORD
1 stop6h 37mDelta
mié. 12/315:40 amORD - GCM
1 stop5h 57mDelta
Deal found 9/13$511
This American Airlines deal was found by Cheapflights users on 9/13. 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. 10/288:25 amGCM - ORD
2 stops8h 48mAmerican Airlines
mar. 11/45:00 amORD - GCM
1 stop5h 56mAmerican Airlines
Deal found 9/13$514
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
mar. 9/2311:30 amGCM - ORD
1 stop21h 48mMultiple Airlines
lun. 9/296:21 pmORD - GCM
2 stops45h 44mMultiple Airlines
Deal found 9/13$554
This Southwest deal was found by Cheapflights users on 9/13. 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.
mié. 12/241:30 pmGCM - ORD
1 stop9h 20mSouthwest
mié. 12/314:25 pmORD - GCM
2 stops19h 10mSouthwest
Deal found 9/13$567
This Flysmarter deal was found by Cheapflights users on 9/13. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/12:00 pmGCM - ORD
2 stops9h 50mBritish Airways
sáb. 11/810:05 pmORD - GCM
2 stops13h 06mBritish Airways
Deal found 9/13$588

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 septiembre 15, 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

mar. 10/28

4:45 pm-10:02 am

1 stop17h 17m

Chicago O'Hare Intl

mar. 11/4

7:10 am-4:30 pm

1 stop8h 20m

$440

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

sáb. 11/1

12:10 pm-11:50 pm

2 stops11h 40m

Chicago O'Hare Intl

sáb. 11/8

6:35 pm-11:57 am

1 stop16h 22m

$483

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

sáb. 11/1

1:50 pm-6:04 pm

Nonstop4h 14m

Chicago O'Hare Intl

sáb. 11/8

6:00 am-4:20 pm

1 stop9h 20m

$497

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

mié. 12/31

5:49 am-4:00 pm

1 stop9h 11m

$505

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mié. 12/24

1:52 pm-7:29 pm

1 stop6h 37m

Chicago O'Hare Intl

mié. 12/31

5:40 am-12:37 pm

1 stop5h 57m

$511

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mar. 10/28

8:25 am-5:13 pm

2 stops8h 48m

Chicago O'Hare Intl

mar. 11/4

5:00 am-11:56 am

1 stop5h 56m

$514

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mié. 12/24

1:30 pm-9:50 pm

1 stop9h 20m

Chicago O'Hare Intl

mié. 12/31

4:25 pm-12:35 pm

2 stops19h 10m

$567

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mar. 3/10

1:50 pm-6:04 pm

Nonstop4h 14m

Chicago O'Hare Intl

mié. 3/11

9:35 pm-3:30 pm

1 stop17h 55m

$578

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

sáb. 11/1

2:00 pm-11:50 pm

2 stops9h 50m

Chicago O'Hare Intl

sáb. 11/8

10:05 pm-12:11 pm

2 stops13h 06m

$588

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mar. 10/28

11:30 am-6:38 pm

3 stops31h 08m

Chicago O'Hare Intl

mar. 11/4

4:03 pm-4:05 pm

2 stops23h 02m

$594

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 19 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
No data available for this route at this time. Please check back soon.

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, American Airlines, and Delta can get you from Cayman Islands to Chicago O'Hare Intl Airport in just under 6h 37m. Your travel time can differ by up to 10h 40m. 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 $387 for a flight from Cayman Islands to Chicago O'Hare Intl Airport. The cheapest flight overall is $326 while the most popular route, (George Town Owen Roberts Intl - Chicago O'Hare Intl) is currently priced at $440.

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

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