MDW - GCM

$202 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
$510
Typical prices: $530-$721
Southwest
Fri 12/7Mon 12/10
MDW - GCM • 1 stop
Cheapest one-way
$202
Typical prices: $162-$383
Southwest
Wed 1/17
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
December
Cheapest • 21% price drop
March
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Atlanta Hartsfield-Jackson (ATL)
Cheapest • Avg $575 (round-trip)
Orlando (MCO)
Shortest trip • 6h 53m (one-way)
Insights
Insights
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Flight Deals
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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

Mon, Dec 7 - Thu, Dec 10
Southwest Logo
5:20 am - 12:35 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
6h 15m1 stop Orlando
Southwest Logo
1:30 pm - 9:20 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
8h 50m1 stop Orlando
$510Southwest
Tue, Dec 1 - Thu, Dec 3
Southwest Logo
4:10 pm - 12:35 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
19h 25m2 stops Las Vegas Harry Reid Intl Orlando
Southwest Logo
1:30 pm - 7:35 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
7h 05m1 stop Orlando
$514Southwest
Wed, Jan 27 - Tue, Feb 2
Southwest Logo
7:50 pm - 12:55 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
16h 05m2 stops Phoenix Sky Harbor Intl Orlando
Southwest Logo
1:50 pm - 5:35 amGCM  George Town Owen Roberts Intl-MDW Chicago Midway
16h 45m2 stops Orlando Las Vegas Harry Reid Intl
$536Southwest
Tue, Dec 1 - Tue, Dec 22
Southwest Logo
4:10 pm - 12:35 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
19h 25m2 stops Las Vegas Harry Reid Intl Orlando
Southwest Logo
1:30 pm - 8:45 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
8h 15m1 stop Orlando
$568Southwest
Sat, Dec 5 - Tue, Dec 8
Southwest Logo
5:00 am - 1:00 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
7h 00m1 stop Orlando
Southwest Logo
1:30 pm - 9:20 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
8h 50m1 stop Orlando
$579Southwest
Sat, Dec 5 - Tue, Dec 8
Southwest Logo
3:20 pm - 12:35 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
20h 15m2 stops Las Vegas Harry Reid Intl Orlando
Southwest Logo
1:30 pm - 10:40 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
10h 10m2 stops Orlando Dallas Love Field
$583Southwest
Sun, Dec 13 - Sun, Dec 20
Southwest Logo
5:10 am - 12:35 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
6h 25m1 stop Orlando
Southwest Logo
1:30 pm - 8:45 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
8h 15m1 stop Orlando
$590Southwest
Sat, Nov 14 - Fri, Nov 20
Southwest Logo
12:55 pm - 12:35 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
22h 40m2 stops Las Vegas Harry Reid Intl Orlando
Southwest Logo
1:30 pm - 6:55 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
6h 25m1 stop Orlando
$613Southwest
Wed, Feb 10 - Sun, Feb 14
Southwest Logo
3:45 pm - 12:55 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
20h 10m2 stops Las Vegas Harry Reid Intl Orlando
Southwest Logo
1:50 pm - 9:45 amGCM  George Town Owen Roberts Intl-MDW Chicago Midway
20h 55m2 stops Orlando Denver Intl
$615Southwest
Mon, Dec 21 - Tue, Dec 29
Delta Logo
6:15 pm - 11:58 amMDW  Chicago Midway-GCM George Town Owen Roberts Intl
16h 43m1 stop Detroit Metropolitan Wayne County
Delta Logo
2:27 pm - 10:22 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
8h 55m1 stop Atlanta Hartsfield-Jackson
$628Delta
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 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 typically range from $530 to $721. The lowest price found in the past 5 days was $510, on Southwest.

What's the cheapest day of the week to fly from Chicago Midway Airport to George Town?

Based on deals KAYAK users found in the last 12 months, Tuesday is the cheapest day of the week to fly from Chicago Midway Airport to George Town. It’s 30% cheaper than the average day, while Friday is the most expensive, with prices 8% higher.

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Key details for Chicago Midway Airport to George Town flights

Low season

August

Cheapest flight

$202
Beat the crowds with an average 86% drop in travelers.
The most popular month to fly with an average 25% increase in travelers.
One-way 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 answers about this route, including flight times, airports, airlines and booking tips.

  • 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.

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

    A nonstop flight from Chicago Midway Airport to George Town takes 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.

  • 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 $721, with an average of $669 over the past 12 months. Anything below $530 counts as a good deal.

  • 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 $510 to $3,385. That means the highest observed fare was about 7x 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 $286, which is 20% above the typical average for this route.

  • 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 averaging $42 for economy cars. Top options include:

    • Europcar
    • Hertz
    • Firefly
    • Alamo
    • Budget

  • 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).

  • 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) - 77% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 23% of one-stop connections

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

    Yes. Flexible dates can save you up to 35% on flights from Chicago Midway Airport to George Town. 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 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 53m, compared with 6h 57m via Atlanta Hartsfield-Jackson (ATL).

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 are flexible, aim for a Tuesday departure and avoid flying on Friday. On this route, Tuesday flights average $473, about $254 less than Friday fares (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 December. Fares historically average $530 round-trip in that month - typically $197 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

Car rentals in George Town
Hotels in George Town
Vacations in George Town