$124 Cheap Flights from Chicago (MDW) to George Town (GCM)

View $124 flight on Wed, Nov 19, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Owen Roberts Intl. Airport (GCM)

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

Prices were available within the past 7 days and start at $124 for one-way flights and $340 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sun, Jan 18 - Wed, Jan 28
MDW
Chicago
GCM
Grand Cayman
$340 Roundtrip, found 6 hours ago
$340
Roundtrip
found 6 hours ago
Select Delta flight, departing Sun, Jan 18 from Chicago to Grand Cayman, returning Wed, Jan 28, priced at $340 found 6 hours ago
Delta
Mon, Feb 23 - Wed, Feb 25
MDW
Chicago
GCM
Grand Cayman
$345 Roundtrip, found 6 days ago
$345
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Feb 23 from Chicago to Grand Cayman, returning Wed, Feb 25, priced at $345 found 6 days ago
Delta
Tue, Nov 18 - Wed, Dec 3
MDW
Chicago
GCM
Grand Cayman
$352 Roundtrip, found 11 hours ago
$352
Roundtrip
found 11 hours ago
Select Delta flight, departing Tue, Nov 18 from Chicago to Grand Cayman, returning Wed, Dec 3, priced at $352 found 11 hours ago
Delta
Mon, Dec 29 - Tue, Dec 30
MDW
Chicago
GCM
Grand Cayman
$357 Roundtrip, found 3 days ago
$357
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Dec 29 from Chicago to Grand Cayman, returning Tue, Dec 30, priced at $357 found 3 days ago
Southwest Airlines
Sun, Dec 7 - Wed, Dec 10
MDW
Chicago
GCM
Grand Cayman
$361 Roundtrip, found 6 days ago
$361
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sun, Dec 7 from Chicago to Grand Cayman, returning Wed, Dec 10, priced at $361 found 6 days ago
Southwest Airlines
Sun, Dec 7 - Wed, Dec 10
MDW
Chicago
GCM
Grand Cayman
$363 Roundtrip, found 6 days ago
$363
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sun, Dec 7 from Chicago to Grand Cayman, returning Wed, Dec 10, priced at $363 found 6 days ago
Southwest Airlines
Sun, Dec 7 - Wed, Dec 10
MDW
Chicago
GCM
Grand Cayman
$364 Roundtrip, found 6 days ago
$364
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sun, Dec 7 from Chicago to Grand Cayman, returning Wed, Dec 10, priced at $364 found 6 days ago
Delta
Sun, Jan 18 - Sun, Feb 1
MDW
Chicago
GCM
Grand Cayman
$365 Roundtrip, found 6 hours ago
$365
Roundtrip
found 6 hours ago
Select Delta flight, departing Sun, Jan 18 from Chicago to Grand Cayman, returning Sun, Feb 1, priced at $365 found 6 hours ago
Southwest Airlines
Sun, Dec 7 - Wed, Dec 10
MDW
Chicago
GCM
Grand Cayman
$370 Roundtrip, found 6 days ago
$370
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sun, Dec 7 from Chicago to Grand Cayman, returning Wed, Dec 10, priced at $370 found 6 days ago
Southwest Airlines
Sun, Dec 7 - Wed, Dec 10
MDW
Chicago
GCM
Grand Cayman
$371 Roundtrip, found 6 days ago
$371
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sun, Dec 7 from Chicago to Grand Cayman, returning Wed, Dec 10, priced at $371 found 6 days ago

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Owen Roberts Intl. Airport (GCM) cost?
Snag a cheap one-way flight from $124 or cheap return flight from $340 from Midway Intl. Airport (MDW) to Owen Roberts Intl. Airport (GCM) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Owen Roberts Intl. Airport (GCM)?
January is the most affordable month to fly from MDW to GCM. Traveling outside of peak seasons is often the key to scoring lower fares.
Which airlines fly direct from Midway Intl. Airport (MDW) to Owen Roberts Intl. Airport (GCM)?
You can't fly directly from Chicago, IL (MDW-Midway Intl.) to Owen Roberts Intl. Airport (GCM). However, you can find other airports that have nonstop flights. Begin your journey at O'Hare Intl. Airport (ORD) and head straight to George Town without a layover.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Owen Roberts Intl. Airport (GCM)?
Use the filters on Expedia to compare different airlines and find the most affordable carrier that'll take you from MDW to GCM. Then, sort your results by "Price (lowest to highest)" to snap up the best deal available.
How many flights per day from Midway Intl. Airport (MDW) to Owen Roberts Intl. Airport (GCM)?
Direct flights from Midway Intl. Airport (MDW) to Owen Roberts Intl. Airport (GCM) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filters. Enter your dates and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to GCM?
Friday is typically the busiest day for flights, while Tuesday tends to be the quietest.* Just remember that flight schedules can change based on a number of factors, such as the carrier and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Owen Roberts Intl. Airport (GCM)?
Book a flight from Midway Intl. Airport (MDW) to Owen Roberts Intl. Airport (GCM) that leaves before 3 PM to reduce the risk of cancellations. Departures after this time have a 22% higher chance of being canceled, on average.**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.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Owen Roberts Intl. Airport (GCM) last-minute?
Last-minute bookings from MDW to GCM are usually more expensive. To lock in the lowest rates, start looking for flights ahead of time. That being said, if you're flexible with your travel plans, you may land a cheap fare right before your journey.
Is it cheaper to book a MDW to GCM flight and hotel package?
Compared with arranging hotels and flights separately, booking a MDW to GCM flight and hotel package with Expedia could lead to significant savings. Better still, having everything in one place will take the stress out of travel planning. Simply pick your flights and select from our wide range of hotels, then personalize your trip with extras like tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Owen Roberts Intl. Airport (GCM)?
Typically, you're able to reschedule or cancel your MDW to GCM flight. However, additional charges may apply, especially if you booked over 24 hours ago. Double-check your itinerary for the airline's guidelines and fees on flight changes, or if you'd like further details, go to our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Owen Roberts Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$340
Distance
1598 mi

Book with confidence

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 January. 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 $124 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.

 

Chicago to George Town Flights
*Available to One Key members.