MDW - GCM

$162 Find Cheap Flights from Chicago Midway Airport to George Town - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$434
Typical prices: $530-$706
Southwest
Sat 1/27Thu 2/1
MDW - GCM • 2 stops
Cheapest one-way
$162
Typical prices: $237-$383
Southwest
Sun 11/11
MDW - GCM • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Chicago Midway Airport and George Town. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
February
Cheapest • 44% price drop
January
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Atlanta Hartsfield-Jackson (ATL)
Cheapest • Avg $556 (round-trip)
Orlando (MCO)
Shortest trip • 6h 42m (one-way)
Insights
Insights
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Flight Deals

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

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to George Town

Wed, Jan 27 - Mon, Feb 1
Southwest Logo
7:55 pm - 12:55 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
16h 00m2 stops Phoenix Sky Harbor Intl Orlando
Southwest Logo
1:50 pm - 5:40 amGCM  George Town Owen Roberts Intl-MDW Chicago Midway
16h 50m2 stops Orlando Las Vegas Harry Reid Intl
$434Southwest
Mon, Jan 11 - Fri, Jan 15
Southwest Logo
5:45 am - 12:55 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
6h 10m1 stop Orlando
Southwest Logo
1:50 pm - 10:55 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
10h 05m1 stop Orlando
$449Southwest
Mon, Jan 11 - Fri, Jan 15
Southwest Logo
5:45 am - 12:55 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
6h 10m1 stop Orlando
Southwest Logo
1:50 pm - 11:00 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
10h 10m2 stops Orlando Nashville Intl
$454Southwest
Mon, Jan 11 - Fri, Jan 15
Southwest Logo
7:30 pm - 12:55 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
16h 25m2 stops Las Vegas Harry Reid Intl Orlando
Southwest Logo
1:50 pm - 5:40 amGCM  George Town Owen Roberts Intl-MDW Chicago Midway
16h 50m2 stops Orlando Las Vegas Harry Reid Intl
$454Southwest
Wed, Jan 27 - Mon, Feb 1
Southwest Logo
7:55 pm - 12:55 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
16h 00m2 stops Phoenix Sky Harbor Intl Orlando
Southwest Logo
1:50 pm - 10:50 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
10h 00m1 stop Orlando
$454Southwest
Wed, Jan 27 - Mon, Feb 1
Southwest Logo
5:45 am - 12:55 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
6h 10m1 stop Orlando
Southwest Logo
1:50 pm - 10:50 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
10h 00m1 stop Orlando
$469Southwest
Thu, Nov 12 - Mon, Nov 16
Southwest Logo
8:25 pm - 12:35 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
15h 10m2 stops Baltimore/Washington Orlando
Southwest Logo
1:30 pm - 10:40 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
10h 10m2 stops Orlando Dallas Love Field
$474Southwest
Thu, Nov 12 - Mon, Nov 16
Southwest Logo
8:25 pm - 12:35 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
15h 10m2 stops Baltimore/Washington Orlando
Southwest Logo
1:30 pm - 9:20 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
8h 50m1 stop Orlando
$474Southwest
Mon, Nov 2 - Sat, Nov 7
Southwest Logo
5:10 am - 12:35 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
6h 25m1 stop Orlando
Southwest Logo
1:55 pm - 8:30 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
7h 35m1 stop Orlando
$478Southwest
Mon, Nov 2 - Sat, Nov 7
Southwest Logo
8:25 pm - 12:35 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
15h 10m2 stops Baltimore/Washington Orlando
Southwest Logo
1:55 pm - 8:30 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
7h 35m1 stop Orlando
$483Southwest
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to George Town flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Chicago Midway Airport to George Town with more confidence.

How much is a round-trip flight from Chicago Midway Airport to George Town?

Round-trip flights from Chicago Midway Airport to George Town start at $434. Prices are below average for this route right now, with typical round-trip fares ranging from $530 to $706. The lowest price found in the past 5 days was $434 on Southwest.

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Key details for Chicago Midway Airport to George Town flights

Low season

September

Cheapest flight

$162
Flight from Chicago Midway Airport to George Town

When to book flights from Midway to George Town

Are your dates flexible? Find out the best times to travel from Midway to George Town based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago Midway Airport to George Town flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airports can I use when flying from Chicago Midway Airport to George Town?

    Flights from Chicago Midway Airport to George Town usually depart from Chicago Midway (MDW) and arrive at George Town Owen Roberts Intl (GCM).

  • What cabin classes can I book on flights from Chicago Midway Airport to George Town?

    Only Economy Class is available on flights from Chicago Midway Airport to George Town.

  • Which airports do connecting flights from Chicago Midway Airport to George Town pass through?

    Connecting flights from Chicago Midway Airport to George Town most commonly pass through:

    • Orlando (MCO) - 75% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 25% of one-stop connections
    Together, these airports account for 100% of one-stop bookings on this route.

  • Can I save money by using flexible dates for flights from Chicago Midway Airport to George Town?

    Yes. Being flexible with your travel dates can save you up to 35% on the Chicago Midway Airport to George Town route. Tuesday is the cheapest departure day at $473 round-trip on average, while Friday is the most expensive at $727, a difference of $254. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How long is a flight from Chicago Midway Airport to George Town?

    A nonstop flight from Chicago Midway Airport to George Town takes 0h 00m, covering 1,598 miles.

  • Do I need a passport to fly from Chicago Midway Airport to George Town?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • Have flight prices from Chicago Midway Airport to George Town changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $434 to $4,331. That means the highest observed fare was about 10x higher than the lowest one.

  • How are flight prices from Chicago Midway Airport to George Town looking right now?

    One-way fares from Chicago Midway Airport to George Town are currently higher than usual. Average one-way flight prices are about $491, which is 28% above the typical average for this route.

  • How much time can I save by choosing a different layover airport from Chicago Midway Airport to George Town?

    Flying via Orlando (MCO) gives the shortest average 1-stop total travel time at 6h 42m, compared with 7h 04m via Atlanta Hartsfield-Jackson (ATL).

  • What car rental options are available at George Town Owen Roberts Intl Airport (GCM)?

    George Town Owen Roberts Intl Airport (GCM) hosts 5 major car rental companies, with daily rates starting from around $6 for economy cars. Top options include:
    • Europcar
    • Hertz
    • Firefly
    • Alamo
    • Budget

  • How much should I expect to pay for a Chicago Midway Airport to George Town flight?

    Round-trip flights from Chicago Midway Airport to George Town range from $530 to $706, with an average of $647 over the past 12 months. Anything below $530 counts as a good deal.

Your guide to booking Chicago Midway Airport to George Town flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Tuesday departure instead of Friday. On this route, Tuesday flights average $473 - about $254 less than Friday (35% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Chicago Midway Airport to George Town trip for February. Fares historically average $365 round-trip in that month - typically $362 less than the most expensive month, which is March (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to George Town Owen Roberts Intl Airport.
    - One Gt Grand Cayman

More options for your flight from Midway to George Town

Complete your trip to George Town with a hotel stay or car rental

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