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O'Hare Intl

$264+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — ORD
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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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 July 31, 2025.

Round-trip from

$410
(Southwest)

One-way from

$264
(Southwest)
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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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 July 31, 2025.

This Southwest deal was found by Cheapflights users on 7/30. 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.
Fri 11/141:30 pmGCM - ORD
1 stop9h 20mSouthwest
Sun 11/166:05 amORD - GCM
1 stop5h 30mSouthwest
Deal found 7/30$410
This Air Canada deal was found by Cheapflights users on 7/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1612:50 pmGCM - ORD
1 stop20h 23mAir Canada
Sun 10/193:35 pmORD - GCM
2 stops20h 20mAir Canada
Deal found 7/31$450
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 9/154:45 pmGCM - ORD
1 stop16h 33mMultiple Airlines
Mon 9/2210:27 amORD - GCM
1 stop10h 53mMultiple Airlines
Deal found 7/31$474
This American Airlines deal was found by Cheapflights users on 7/31. 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.
Wed 9/312:10 pmGCM - ORD
2 stops19h 32mAmerican Airlines
Sat 9/68:29 pmORD - GCM
2 stops14h 41mAmerican Airlines
Deal found 7/31$624
This United Airlines deal was found by Cheapflights users on 7/31. 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 8/161:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
Mon 8/186:00 amORD - GCM
1 stop6h 30mUnited Airlines
Deal found 7/31$899
This Delta deal was found by Cheapflights users on 7/30. 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.
Thu 10/1612:55 pmGCM - ORD
1 stop11h 02mDelta
Sun 10/195:20 amORD - GCM
1 stop6h 15mDelta
Deal found 7/30$2,211

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 July 31, 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

Fri 11/14

1:30 pm-9:50 pm

1 stop9h 20m

Chicago O'Hare Intl

Sun 11/16

6:05 am-12:35 pm

1 stop5h 30m

$410

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 10/16

12:50 pm-9:13 am

1 stop20h 23m

Chicago O'Hare Intl

Sun 10/19

3:35 pm-11:55 am

2 stops20h 20m

$450

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 9/15

4:45 pm-9:18 am

1 stop16h 33m

Chicago O'Hare Intl

Mon 9/22

10:27 am-9:20 pm

1 stop10h 53m

$474

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 9/3

12:10 pm-7:42 am

2 stops19h 32m

Chicago O'Hare Intl

Sat 9/6

8:29 pm-11:10 am

2 stops14h 41m

$624

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 8/16

1:45 pm-6:07 pm

Nonstop4h 22m

Chicago O'Hare Intl

Mon 8/18

6:00 am-12:30 pm

1 stop6h 30m

$899

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 10/16

12:55 pm-11:57 pm

1 stop11h 02m

Chicago O'Hare Intl

Sun 10/19

5:20 am-11:35 am

1 stop6h 15m

$2,211

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 1/14

1:50 pm-9:50 pm

1 stop9h 00m

$264

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 10/31

12:30 pm-1:01 pm

1 stop24h 31m

$275

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 8/29

4:45 pm-9:22 am

1 stop16h 37m

$291

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 1/14

2:00 pm-5:10 pm

Nonstop4h 10m

$387

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 12 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

What is the cheapest time of day to fly from LAW to ORD?

Find hourly flight availability from Grand Cayman 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 July 31, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Grand Cayman to Chicago O'Hare Intl Airport as you normally would.

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to O'Hare Intl. Reviews last updated July 31, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Grand Cayman to Chicago O'Hare Intl Airport by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Air Canada
7.1
Good
9,851 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • What are the cheapest airlines to fly from Grand Cayman to Chicago O'Hare Intl Airport one-way?

    The cheapest airlines for a one-way flight from Grand Cayman to Chicago O'Hare Intl Airport are Southwest ($264), Air Canada ($275), and American Airlines ($387).

  • 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 $924, our data shows the cheapest flight currently is $295. When looking at the most popular route, (George Town Owen Roberts Intl - Chicago O'Hare Intl), you can expect to pay $410 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
Beloit
Hoffman Estates
Skokie
Naperville
Des Plaines
Elgin
Arlington Heights
Elk Grove Village
Racine
Rockford
Tinley Park
Orland Park
Merrillville
Downers Grove
Evanston
Lake Geneva
Gurnee
Joliet

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