$146 Cheap Flights from Chicago (ORD) to George Town (GCM)

View $146 flight on Tue, Dec 9, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Owen Roberts Intl. Airport (GCM)

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • one key icon

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Chicago to George Town (ORD-GCM)

Prices were available within the past 7 days and start at $146 for one-way flights and $406 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sun, Nov 9 - Thu, Nov 13
ORD
Chicago
GCM
Grand Cayman
$406 Roundtrip, found 7 hours ago
$406
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Sun, Nov 9 from Chicago to Grand Cayman, returning Thu, Nov 13, priced at $406 found 7 hours ago
Southwest Airlines
Sun, Nov 9 - Thu, Nov 13
ORD
Chicago
GCM
Grand Cayman
$416 Roundtrip, found 7 hours ago
$416
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Sun, Nov 9 from Chicago to Grand Cayman, returning Thu, Nov 13, priced at $416 found 7 hours ago
Air Canada
Sun, Oct 19 - Thu, Oct 23
ORD
Chicago
GCM
Grand Cayman
$417 Roundtrip, found 3 days ago
$417
Roundtrip
found 3 days ago
Select Air Canada flight, departing Sun, Oct 19 from Chicago to Grand Cayman, returning Thu, Oct 23, priced at $417 found 3 days ago
Southwest Airlines
Mon, Nov 17 - Thu, Nov 20
ORD
Chicago
GCM
Grand Cayman
$418 Roundtrip, found 16 hours ago
$418
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Mon, Nov 17 from Chicago to Grand Cayman, returning Thu, Nov 20, priced at $418 found 16 hours ago
Southwest Airlines
Mon, Nov 17 - Thu, Nov 20
ORD
Chicago
GCM
Grand Cayman
$420 Roundtrip, found 16 hours ago
$420
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Mon, Nov 17 from Chicago to Grand Cayman, returning Thu, Nov 20, priced at $420 found 16 hours ago
JetBlue Airways
Fri, Oct 31 - Fri, Nov 7
ORD
Chicago
GCM
Grand Cayman
$422 Roundtrip, found 5 days ago
$422
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Fri, Oct 31 from Chicago to Grand Cayman, returning Fri, Nov 7, priced at $422 found 5 days ago
Southwest Airlines
Sun, Nov 9 - Thu, Nov 13
ORD
Chicago
GCM
Grand Cayman
$436 Roundtrip, found 7 hours ago
$436
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Sun, Nov 9 from Chicago to Grand Cayman, returning Thu, Nov 13, priced at $436 found 7 hours ago
JetBlue Airways
Fri, Oct 31 - Sat, Nov 8
ORD
Chicago
GCM
Grand Cayman
$438 Roundtrip, found 2 days ago
$438
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Fri, Oct 31 from Chicago to Grand Cayman, returning Sat, Nov 8, priced at $438 found 2 days ago
Delta
Mon, Oct 27 - Fri, Oct 31
ORD
Chicago
GCM
Grand Cayman
$448 Roundtrip, found 2 days ago
$448
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Oct 27 from Chicago to Grand Cayman, returning Fri, Oct 31, priced at $448 found 2 days ago
American Airlines
Fri, Oct 31 - Fri, Nov 7
ORD
Chicago
GCM
Grand Cayman
$449 Roundtrip, found 5 days ago
$449
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Oct 31 from Chicago to Grand Cayman, returning Fri, Nov 7, priced at $449 found 5 days ago

Find the cheapest month to fly from Chicago (ORD) to George Town (GCM)

November is typically the cheapest month to fly

From $407 - $803 per traveler.

Graph displaying average flight prices per month

Alternative airports near George Town

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Owen Roberts Intl. GCM. Cheapest option available. Flights from $744
GCM
Owen Roberts Intl.
Cheapest
Flights from $744
Flights from Chicago (ORD) to George Town (GCM)
Origin airport
O'Hare Intl.
Destination airport
Owen Roberts Intl.
Airlines serving
Air Canada, American Airlines, Delta, JetBlue Airways, Southwest Airlines, United
Roundtrip price
$405
Distance
1613 mi

Chicago to George Town Flights

The cheapest times to fly from Chicago to George Town

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to George Town are during the month of November. You can find some of the cheapest flights from Chicago to George Town with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to George Town

Sunday is one of the best days to book for cheap flights from Chicago to George Town: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to George Town

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to George Town in 2025. You can also book with separate airlines for your outbound and return journeys, from $146 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to George Town flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to George Town airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Owen Roberts Intl. Airport (GCM) cost?
Snag cheap return flights starting from $865 from O'Hare Intl. Airport (ORD) to Owen Roberts Intl. Airport (GCM). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a United flight leaving ORD on July 26 2025 and touching down at GCM. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from ORD to GCM?
The cheapest flights from ORD to GCM are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Owen Roberts Intl. Airport (GCM)?
Catch a nonstop flight with United Airlines and go straight from O'Hare Intl. Airport (ORD) to Owen Roberts Intl. Airport (GCM).
What is the cheapest airline that flies from ORD to GCM?
Take off from ORD to GCM with United. This airline currently has the lowest one-way fare for this route, starting from $498. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on July 26 2025. Prices were last updated on July 23 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Owen Roberts Intl. Airport (GCM)?
On average, you can choose from 2 direct weekly flights from O'Hare Intl. Airport (ORD) to Owen Roberts Intl. Airport (GCM). To increase your travel options, consider flights with layovers. Just enter your dates on Expedia and then filter your search to show one stop or more.
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Owen Roberts Intl. Airport (GCM)?
More people fly between ORD and GCM at 8 AM than at any other time of day. Looking for a quieter experience? Consider flying outside peak hours and you could save on your ticket as well.
What day of the week has the most flights from ORD to GCM?
Jet off on a Saturday if you're after the biggest selection of flights from O'Hare Intl. Airport (ORD) to Owen Roberts Intl. Airport (GCM).
What is the earliest flight from O'Hare Intl. Airport (ORD) to Owen Roberts Intl. Airport (GCM)?
O'Hare Intl. Airport (ORD)'s earliest flight to Owen Roberts Intl. Airport (GCM) departs at approximately 8:39AM UTC-6. With a travel duration of 3h 56m, you'll land at around 1:35PM UTC-5.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Owen Roberts Intl. Airport (GCM)?
Flights from ORD to GCM have an average travel time of 4 hours and 3 minutes. The total distance between the two is 1,600 mi.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Owen Roberts Intl. Airport (GCM)?
To touch down at Owen Roberts Intl. Airport (GCM) without delays, pick a flight that leaves O'Hare Intl. Airport (ORD) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for George Town from O'Hare Intl. Airport (ORD)?
If you're taking a direct flight from O'Hare Intl. Airport (ORD) to George Town, Owen Roberts Intl. Airport (GCM) is the only airport you can land at.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Owen Roberts Intl. Airport (GCM) last-minute?
Last-minute fares from ORD to GCM are typically more expensive. To lock in the best prices, start searching for flights early. That being said, if you can play around with your travel dates, you may score a cheap fare right before your journey.
Is it cheaper to book an ORD to GCM flight and hotel package?
You can save money by booking an ORD to GCM flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one place. Once you've chosen your preferred flights and accommodations, consider adding extras such as car rentals, activities and tours.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Owen Roberts Intl. Airport (GCM)?
If you reserved your ORD to GCM flight within the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Explore a world of travel with Expedia

*Available to One Key members.