$230 Cheap Flights from George Town (GCM) to Chicago (ORD)

View $230 flight on Tue, Jan 13, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at $230 for one-way flights and $247 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Sat, Jan 24 - Sat, Jan 31
GCM
Grand Cayman
ORD
Chicago
$247 Roundtrip, found 5 days ago
$247
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Sat, Jan 24 from Grand Cayman to Chicago, returning Sat, Jan 31, priced at $247 found 5 days ago
Spirit Airlines
Thu, Feb 19 - Sat, Feb 28
GCM
Grand Cayman
ORD
Chicago
$269 Roundtrip, found 5 days ago
$269
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Thu, Feb 19 from Grand Cayman to Chicago, returning Sat, Feb 28, priced at $269 found 5 days ago
Spirit Airlines
Sat, Jan 10 - Sun, Jan 18
GCM
Grand Cayman
ORD
Chicago
$290 Roundtrip, found 4 days ago
$290
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sat, Jan 10 from Grand Cayman to Chicago, returning Sun, Jan 18, priced at $290 found 4 days ago
Air Canada
Mon, Jan 19 - Fri, Jan 23
GCM
Grand Cayman
ORD
Chicago
$303 Roundtrip, found 6 days ago
$303
Roundtrip
found 6 days ago
Select Air Canada flight, departing Mon, Jan 19 from Grand Cayman to Chicago, returning Fri, Jan 23, priced at $303 found 6 days ago
Spirit Airlines
Thu, Feb 26 - Sat, Mar 7
GCM
Grand Cayman
ORD
Chicago
$307 Roundtrip, found 5 days ago
$307
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Thu, Feb 26 from Grand Cayman to Chicago, returning Sat, Mar 7, priced at $307 found 5 days ago
Air Canada
Fri, Jan 23 - Fri, Jan 30
GCM
Grand Cayman
ORD
Chicago
$323 Roundtrip, found 5 days ago
$323
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri, Jan 23 from Grand Cayman to Chicago, returning Fri, Jan 30, priced at $323 found 5 days ago
Air Canada
Mon, Jan 26 - Fri, Jan 30
GCM
Grand Cayman
ORD
Chicago
$325 Roundtrip, found 3 days ago
$325
Roundtrip
found 3 days ago
Select Air Canada flight, departing Mon, Jan 26 from Grand Cayman to Chicago, returning Fri, Jan 30, priced at $325 found 3 days ago
Southwest Airlines
Wed, Feb 4 - Sun, Feb 8
GCM
Grand Cayman
ORD
Chicago
$349 Roundtrip, found 2 days ago
$349
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Feb 4 from Grand Cayman to Chicago, returning Sun, Feb 8, priced at $349 found 2 days ago
American Airlines
Wed, Dec 24 - Thu, Jan 1
GCM
Grand Cayman
ORD
Chicago
$362 Roundtrip, found 4 days ago
$362
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Dec 24 from Grand Cayman to Chicago, returning Thu, Jan 1, priced at $362 found 4 days ago
United
Tue, Mar 31 - Sun, Apr 19
GCM
Grand Cayman
ORD
Chicago
$438 Roundtrip, just found
$438
Roundtrip
just found
Select United flight, departing Tue, Mar 31 from Grand Cayman to Chicago, returning Sun, Apr 19, priced at $438 just found

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

January is typically the cheapest month to fly

From $296 - $895 per traveler.

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $714
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $714
Flights from George Town (GCM) to Chicago (ORD)
Origin airport
Owen Roberts Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, American Airlines, Delta, JetBlue Airways, Southwest Airlines, United
Roundtrip price
$247
Distance
1613 mi
Average flight time
3 hours 12 mins

George Town to Chicago Flights

The cheapest times to fly from George Town to Chicago

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 George Town to Chicago are during the month of January. You can find some of the cheapest flights from George Town to Chicago with Expedia's search tool and vast selection of airlines.

 

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

Sunday is one of the best days to book for cheap flights from George Town to Chicago: 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 George Town to Chicago

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 George Town to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $230 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 George Town to Chicago 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 George Town to Chicago 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 Owen Roberts Intl. Airport (GCM) to O'Hare Intl. Airport (ORD) cost?
Secure a cheap one-way flight from $230 or cheap return flight from $247 from Owen Roberts Intl. Airport (GCM) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Owen Roberts Intl. Airport (GCM) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from GCM to ORD is January, when there's less demand. Off-peak season is usually when better flight deals are available between these airports.
Which airlines fly direct from Owen Roberts Intl. Airport (GCM) to O'Hare Intl. Airport (ORD)?
Fly nonstop from Owen Roberts Intl. Airport (GCM) to O'Hare Intl. Airport (ORD) on an American Airlines flight.
What is the cheapest airline that flies from Owen Roberts Intl. Airport (GCM) to O'Hare Intl. Airport (ORD)?
The cheapest airline to offer flights between Owen Roberts Intl. Airport (GCM) and O'Hare Intl. Airport (ORD) can vary based on when you plan to fly. American Airlines and United Airlines are just some well-known options offering well-priced fares. Use Expedia's filter tool to compare airlines in one place and find the right GCM to ORD flight that fits your budget.
How many flights per day from Owen Roberts Intl. Airport (GCM) to O'Hare Intl. Airport (ORD)?
On average, Owen Roberts Intl. Airport (GCM) offers 2 nonstop flights to O'Hare Intl. Airport (ORD) per week. For more choice, use Expedia's filter tool to find flights with a layover. Squeeze in a quick visit to another city or just break up your journey.
What are the most popular departure times for flights from Owen Roberts Intl. Airport (GCM) to O'Hare Intl. Airport (ORD)?
Flights between GCM and ORD tend to be busiest at 2 PM. For a more relaxed experience and possibly cheaper tickets, choose a time outside the usual busy windows.
What day of the week has the most flights from GCM to ORD?
If you depart on a Saturday, you'll get the biggest range of choices for flights from Owen Roberts Intl. Airport (GCM) to O'Hare Intl. Airport (ORD).
What is the earliest flight from Owen Roberts Intl. Airport (GCM) to O'Hare Intl. Airport (ORD)?
The first flight of the day leaving from Owen Roberts Intl. Airport (GCM) is at around 2:40PM UTC-5. Board this flight and you'll reach O'Hare Intl. Airport (ORD) at approximately 5:56PM UTC-6. The entire trip takes 4h 16m.
How long does it take to fly from Owen Roberts Intl. Airport (GCM) to O'Hare Intl. Airport (ORD)?
Flights from GCM to ORD have an average travel time of 4 hours and 13 minutes. The total distance between these two airports is 1,600 mi.
What airline has the least delays from GCM to ORD?
With 90% of journeys usually arriving on time, United Airlines has the best on-time performance for direct flights from Owen Roberts Intl. Airport (GCM) to O'Hare Intl. Airport (ORD). To check your flight status and get notifications if anything changes, head to the Expedia App.
What is the best time to fly from Owen Roberts Intl. Airport (GCM) to O'Hare Intl. Airport (ORD)?
Select a flight from Owen Roberts Intl. Airport (GCM) to O'Hare Intl. Airport (ORD) that takes off before 3 PM to reduce the risk of cancellations and delays. Later departures are on average 22% more likely to be canceled.**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 Chicago from Owen Roberts Intl. Airport (GCM)?
If you've booked a direct flight from Owen Roberts Intl. Airport (GCM) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Owen Roberts Intl. Airport (GCM) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute bookings from GCM to ORD are typically more expensive. To secure the cheapest rates, start looking for flights early. That said, if your travel plans are flexible, you may find a cheap fare right before your journey.
Is it cheaper to book a GCM to ORD flight and hotel package?
Opting for a GCM to ORD flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Pick from our impressive range of stays and then add car rentals, activities and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Owen Roberts Intl. Airport (GCM) to O'Hare Intl. Airport (ORD)?
Typically, you're able to cancel or reschedule your GCM to ORD flight. However, additional fees may apply, especially if you booked more than 24 hours ago. Double-check your itinerary for the airline's fees and guidelines on flight changes, or if you'd like further information, visit our Customer Service portal.

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*Available to One Key members.