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

$292+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — ORD
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
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 April 4, 2025.

Round-trip from

$646
(American Airlines)

One-way from

$292
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$908
From Grand Cayman to Chicago O'Hare Intl
Search Deals
One-way flight from Grand Cayman to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 32% potential increase in price ($324 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($45 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
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 April 4, 2025.

This American Airlines deal was found by Cheapflights users on 4/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1612:25 pmGCM - ORD
1 stop20h 36mAmerican Airlines
Tue 5/205:00 amORD - GCM
1 stop6h 10mAmerican Airlines
Deal found 4/3$646
This Delta deal was found by Cheapflights users on 4/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2512:47 pmGCM - ORD
1 stop8h 03mDelta
Mon 4/285:30 amORD - GCM
1 stop5h 52mDelta
Deal found 4/3$691
This Mytrip deal was found by Cheapflights users on 4/3. 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.
Fri 4/185:35 pmGCM - ORD
2 stops31h 23mMultiple Airlines
Tue 4/226:19 pmORD - GCM
2 stops43h 11mMultiple Airlines
Deal found 4/3$871
This United Airlines deal was found by Cheapflights users on 4/3. 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.
Sat 5/171:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
Tue 5/209:50 pmORD - GCM
1 stop14h 40mUnited Airlines
Deal found 4/3$1,418
This Air Canada deal was found by Cheapflights users on 4/3. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1512:50 pmGCM - ORD
2 stops22h 42mAir Canada
Sat 5/173:35 pmORD - GCM
2 stops44h 20mAir Canada
Deal found 4/3$4,372

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 April 4, 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 5/16

12:25 pm-9:01 am

1 stop20h 36m

Chicago O'Hare Intl

Tue 5/20

5:00 am-11:10 am

1 stop6h 10m

$646

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 4/25

12:47 pm-8:50 pm

1 stop8h 03m

Chicago O'Hare Intl

Mon 4/28

5:30 am-11:22 am

1 stop5h 52m

$691

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 4/18

5:35 pm-12:58 am

2 stops31h 23m

Chicago O'Hare Intl

Tue 4/22

6:19 pm-1:30 pm

2 stops43h 11m

$871

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 5/17

1:45 pm-6:07 pm

Nonstop4h 22m

Chicago O'Hare Intl

Tue 5/20

9:50 pm-12:30 pm

1 stop14h 40m

$1,418

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 5/15

12:50 pm-11:32 am

2 stops22h 42m

Chicago O'Hare Intl

Sat 5/17

3:35 pm-11:55 am

2 stops44h 20m

$4,372

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 4/30

7:00 am-2:26 pm

1 stop7h 26m

$292

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 5/31

11:40 am-9:54 pm

1 stop10h 14m

$312

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 6/5

12:50 pm-9:09 am

1 stop20h 19m

$314

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 4/12

7:05 pm-8:19 pm

1 stop25h 14m

$342

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 6/3

1:35 pm-11:12 pm

1 stop9h 37m

$393

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

Showing 1-10 of 11 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 April 4, 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.

Rainfall in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago O'Hare Intl Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 1.7 in.

Temperature in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 4, 2025.
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,899 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,618 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
JetBlue
7.3
Good
2,920 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Air Canada
7.0
Good
9,040 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 JetBlue ($312), Air Canada ($314), and Sun Country Air ($342).

  • What are the most reliable airlines from Grand Cayman to Chicago O'Hare Intl Airport?

    Consider American Airlines (89%), United Airlines (73%) or Qatar Airways (67%) when booking your flight. These represent the most reliable airlines when flying from Grand Cayman to Chicago O'Hare Intl Airport.

  • 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 $646, our data shows the cheapest flight currently is $321. When looking at the most popular route, (George Town Owen Roberts Intl - Chicago O'Hare Intl), you can expect to pay $560 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 Grand Cayman?

Book flights to Grand Cayman if you plan to visit one of these locations
Schaumburg
Rosemont
Beloit
Racine
Hoffman Estates
Naperville
Rockford
Tinley Park
Skokie
Kenosha
Arlington Heights
Joliet
Orland Park
Merrillville
Northbrook
New Buffalo
Evanston
Waukegan
Elgin
Glenview

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.