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O'Hare Intl

$175+ Cheap flights from Grand Cayman 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
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Find flight deals from Grand Cayman to O'Hare Intl

Cheapest flights from Grand Cayman to O'Hare Intl
Explore the most affordable flight options available from Grand Cayman to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

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.
Tue 12/25:45 pmGCM - ORD
1 stop28h 31mUnited Airlines
Tue 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.
Thu 11/135:45 pmGCM - ORD
1 stop27h 11mUnited Airlines
Sun 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.
Thu 11/131:20 pmGCM - ORD
2 stops9h 03mAmerican Airlines
Sun 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.
Thu 11/135:45 pmGCM - ORD
1 stop27h 11mUnited Airlines
Mon 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.
Tue 12/21:25 pmGCM - ORD
2 stops10h 03mAmerican Airlines
Tue 12/97:07 pmORD - GCM
1 stop16h 17mAmerican 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.
Thu 11/131:20 pmGCM - ORD
2 stops9h 03mAmerican Airlines
Mon 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.
Wed 12/242:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Sun 12/289:23 pmORD - GCM
1 stop17h 37mUnited Airlines
Deal found 11/2$447
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.
Wed 11/1911:30 amGCM - ORD
1 stop24h 05mMultiple Airlines
Sun 11/2311:40 amORD - GCM
1 stop22h 55mMultiple Airlines
Deal found 11/1$483
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/211:30 amGCM - ORD
3 stops26h 53mMultiple Airlines
Tue 12/99:14 pmORD - GCM
2 stops17h 51mMultiple Airlines
Deal found 11/2$514

Cheap flight deals from Grand Cayman to O'Hare Intl

Keep the following information in mind while searching for Grand Cayman to O'Hare Intl flight deals. Data was last updated November 3, 2025.

Round-trip from

$375
(United Airlines)

One-way from

$175
(Flightnetwork)

Popular in

March

Cheapest in

October

Average price

$736
From Grand Cayman to Chicago O'Hare Intl
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One-way flight from Grand Cayman 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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Cheapflights Fare Finder

 
Customize your flight search to find flights from Grand Cayman 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 November 3, 2025.
Use the filters below to find and compare flights from Grand Cayman to Chicago O'Hare Intl Airport that are best for you.

Fly from

Grand Cayman

Fly to

O'Hare Intl

Route

Depart

Return

Price

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 12/2

5:45 pm-9:16 pm

1 stop28h 31m

Chicago O'Hare Intl

Tue 12/9

8:49 am-4:30 pm

1 stop6h 41m

$343

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 11/13

5:45 pm-7:56 pm

1 stop27h 11m

Chicago O'Hare Intl

Sun 11/16

8:50 am-4:30 pm

1 stop6h 40m

$375

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 11/13

1:20 pm-9:23 pm

2 stops9h 03m

Chicago O'Hare Intl

Sun 11/16

5:00 am-11:57 am

1 stop5h 57m

$388

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 11/13

5:45 pm-7:56 pm

1 stop27h 11m

Chicago O'Hare Intl

Mon 11/17

6:00 am-4:30 pm

1 stop9h 30m

$397

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 12/2

9:00 am-5:52 pm

2 stops9h 52m

Chicago O'Hare Intl

Tue 12/9

8:55 pm-12:05 pm

2 stops14h 10m

$407

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 12/24

2:50 pm-6:04 pm

Nonstop4h 14m

Chicago O'Hare Intl

Sun 12/28

9:23 pm-4:00 pm

1 stop17h 37m

$447

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 11/19

11:30 am-10:35 am

1 stop24h 05m

Chicago O'Hare Intl

Sun 11/23

11:40 am-11:35 am

1 stop22h 55m

$483

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 12/2

11:30 am-1:23 pm

3 stops26h 53m

Chicago O'Hare Intl

Tue 12/9

9:14 pm-4:05 pm

2 stops17h 51m

$514

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 12/24

7:00 am-10:07 pm

2 stops16h 07m

Chicago O'Hare Intl

Sun 12/28

5:00 am-1:45 pm

1 stop7h 45m

$583

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 12/4

2:40 pm-8:01 pm

1 stop6h 21m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 20 results
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Best time to book a flight from Grand Cayman to O'Hare Intl

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

    For as low as $388, United Airlines can have you in Chicago O'Hare Intl Airport from Grand Cayman in 9h 03m. Airlines will cover a distance of 1613 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    While on average a flight from Grand Cayman to Chicago O'Hare Intl Airport is generally $506, our data shows the cheapest flight currently is $365. When looking at the most popular route, (George Town Owen Roberts Intl - Chicago O'Hare Intl), you can expect to pay $343 for that flight.

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

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

  • How can I find direct flights from Grand Cayman 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 Grand Cayman to O'Hare Intl.

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

    Yes. Cheapflights offers flight deals from Grand Cayman 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 Grand Cayman to O'Hare Intl

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