HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
O'Hare Intl

$208+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — ORD
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Grand Cayman to O'Hare Intl with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 17, 2025.

Round-trip from

$471
(American Airlines)

One-way from

$208
(Priceline)
From Grand Cayman to Chicago O'Hare Intl
Search Deals
One-way flight from Grand Cayman to Chicago O'Hare Intl
Search Deals

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 September 17, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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.
Sat 10/412:25 pmGCM - ORD
1 stop8h 02mAmerican Airlines
Sat 10/117:05 pmORD - GCM
1 stop16h 05mAmerican Airlines
Deal found 9/15$471
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Sat 11/18:25 amGCM - ORD
1 stop15h 33mAmerican Airlines
Sat 11/87:07 pmORD - GCM
1 stop16h 06mAmerican Airlines
Deal found 9/17$477
This Delta deal was found by Cheapflights users on 9/15. 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.
Sat 10/412:52 pmGCM - ORD
2 stops19h 13mDelta
Sat 10/115:20 amORD - GCM
1 stop6h 15mDelta
Deal found 9/15$487
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Sat 11/11:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Sat 11/88:48 amORD - GCM
1 stop6h 47mUnited Airlines
Deal found 9/17$492
This Mytrip deal was found by Cheapflights users on 9/15. 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.
Sat 10/48:50 amGCM - ORD
2 stops23h 34mMultiple Airlines
Sat 10/117:43 pmORD - GCM
2 stops21h 37mMultiple Airlines
Deal found 9/15$598
This KAYAK deal was found by Cheapflights users on 9/16. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2412:25 pmGCM - ORD
1 stop8h 02mAmerican Airlines
Sat 9/278:47 pmORD - GCM
1 stop14h 35mAmerican Airlines
Deal found 9/16$618
This Mytrip deal was found by Cheapflights users on 9/17. 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.
Sat 11/18:50 amGCM - ORD
3 stops16h 13mMultiple Airlines
Sat 11/88:50 pmORD - GCM
2 stops23h 25mMultiple Airlines
Deal found 9/17$673

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 September 17, 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

Sat 11/1

8:25 am-11:58 pm

1 stop15h 33m

Chicago O'Hare Intl

Sat 11/8

7:07 pm-12:13 pm

1 stop16h 06m

$477

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 10/4

12:52 pm-8:05 am

2 stops19h 13m

Chicago O'Hare Intl

Sat 10/11

5:20 am-11:35 am

1 stop6h 15m

$487

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 11/1

1:50 pm-6:04 pm

Nonstop4h 14m

Chicago O'Hare Intl

Sat 11/8

8:45 am-1:45 pm

Nonstop4h 00m

$487

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 3/10

1:50 pm-6:04 pm

Nonstop4h 14m

Chicago O'Hare Intl

Wed 3/11

9:35 pm-3:30 pm

1 stop17h 55m

$578

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 10/4

8:50 am-8:24 am

2 stops23h 34m

Chicago O'Hare Intl

Sat 10/11

7:43 pm-5:20 pm

2 stops21h 37m

$598

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 3/10

1:00 pm-5:10 pm

Nonstop4h 10m

Chicago O'Hare Intl

Wed 3/11

8:10 am-11:56 am

Nonstop3h 46m

$615

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sun 12/14

11:55 am-7:21 pm

1 stop8h 26m

$238

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 12/13

11:55 am-9:00 pm

1 stop10h 05m

$238

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 12/18

11:55 am-9:00 pm

1 stop10h 05m

$238

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sun 12/14

11:55 am-9:23 am

1 stop22h 28m

$238

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 13 results
1
2

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 $487, American Airlines can have you in Chicago O'Hare Intl Airport from Grand Cayman in 4h 14m. 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 $387, our data shows the cheapest flight currently is $326. When looking at the most popular route, (George Town Owen Roberts Intl - Chicago O'Hare Intl), you can expect to pay $578 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.

  • What is the cheapest month to book a flight from Grand Cayman to Chicago O'Hare Intl Airport?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Grand Cayman to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
George Town to O'Hare Intl flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.