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Cheap flights from Chicago Midway Airport to George Town from $185

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to George Town departing on 11/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to George Town

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:10 am - 11:55 am
MDW
-
GCM
6h 45m
1 stop
Southwest Logo
12:50 pm - 10:05 pm
GCM
-
MDW
9h 15m
1 stop
$356Southwest
Wed, Jul 15 - Wed, Jul 22
Southwest Logo
5:10 am - 11:55 am
MDW
-
GCM
6h 45m
1 stop
Southwest Logo
12:50 pm - 11:15 pm
GCM
-
MDW
10h 25m
2 stops
$448Southwest
Wed, Jul 15 - Wed, Jul 22
Southwest Logo
5:10 am - 12:35 pm
MDW
-
GCM
6h 25m
1 stop
Southwest Logo
1:30 pm - 10:40 pm
GCM
-
MDW
10h 10m
2 stops
$480Southwest
Fri, Nov 13 - Mon, Nov 16
Southwest Logo
5:10 am - 11:55 am
MDW
-
GCM
6h 45m
1 stop
Southwest Logo
1:05 pm - 10:25 pm
GCM
-
MDW
9h 20m
1 stop
$514Southwest
Tue, Jun 16 - Sat, Jun 20
Southwest Logo
7:35 pm - 11:55 am
MDW
-
GCM
16h 20m
2 stops
Southwest Logo
1:05 pm - 10:25 pm
GCM
-
MDW
9h 20m
1 stop
$519Southwest
Tue, Jun 16 - Sat, Jun 20
Southwest Logo
3:40 pm - 1:00 pm
MDW
-
GCM
20h 20m
2 stops
Southwest Logo
1:30 pm - 10:40 pm
GCM
-
MDW
10h 10m
2 stops
$541Southwest
Fri, Nov 13 - Mon, Nov 16
Southwest Logo
6:30 am - 11:55 am
MDW
-
GCM
5h 25m
1 stop
Southwest Logo
12:50 pm - 9:25 pm
GCM
-
MDW
8h 35m
1 stop
$551Southwest
Mon, Jun 29 - Mon, Jul 6
Southwest Logo
6:30 am - 11:55 am
MDW
-
GCM
5h 25m
1 stop
Southwest Logo
12:50 pm - 12:10 am
GCM
-
MDW
11h 20m
2 stops
$556Southwest
Mon, Jun 29 - Mon, Jul 6
Southwest Logo
3:05 pm - 12:35 pm
MDW
-
GCM
20h 30m
2 stops
Southwest Logo
1:30 pm - 7:35 pm
GCM
-
MDW
7h 05m
1 stop
$558Southwest
Sat, Nov 7 - Wed, Nov 11
Multiple Airlines Logo
10:25 am - 12:45 pm
MDW
-
GCM
26h 20m
1 stop
Multiple Airlines Logo
1:45 pm - 9:40 am
GCM
-
MDW
19h 55m
1 stop
$571Multiple Airlines
Fri, Jun 19 - Tue, Jun 23

Southwest flights from Chicago Midway Airport to George Town

Our best Southwest deals on Chicago Midway Airport to George Town flight tickets
Southwest
Jul 15
MDW5:10 amChicago Midway
6h 45m
1 stop
GCM11:55 amGeorge Town Owen Roberts Intl
Jul 22
GCM12:50 pmGeorge Town Owen Roberts Intl
9h 15m
1 stop
MDW10:05 pmChicago Midway
$356
Southwest
Jul 15
MDW5:10 amChicago Midway
6h 45m
1 stop
GCM11:55 amGeorge Town Owen Roberts Intl
Jul 22
GCM12:50 pmGeorge Town Owen Roberts Intl
10h 25m
2 stops
MDW11:15 pmChicago Midway
$448
Southwest
Nov 13
MDW5:10 amChicago Midway
6h 25m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
Nov 16
GCM1:30 pmGeorge Town Owen Roberts Intl
10h 10m
2 stops
MDW10:40 pmChicago Midway
$480

Delta flights from Chicago Midway Airport to George Town

Our best Delta deals on Chicago Midway Airport to George Town flight tickets
Delta
Sep 4
MDW6:05 amChicago Midway
5h 34m
1 stop
GCM11:39 amGeorge Town Owen Roberts Intl
Sep 8
GCM12:56 pmGeorge Town Owen Roberts Intl
8h 50m
1 stop
MDW9:46 pmChicago Midway
$626
Delta
Sep 4
MDW6:42 pmChicago Midway
16h 57m
2 stops
GCM11:39 amGeorge Town Owen Roberts Intl
Sep 8
GCM12:56 pmGeorge Town Owen Roberts Intl
8h 50m
1 stop
MDW9:46 pmChicago Midway
$631
Delta
Sep 3
MDW6:42 pmChicago Midway
16h 57m
2 stops
GCM11:39 amGeorge Town Owen Roberts Intl
Sep 8
GCM12:56 pmGeorge Town Owen Roberts Intl
8h 50m
1 stop
MDW9:46 pmChicago Midway
$641

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to George Town that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated June 1, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to George Town that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 7/15

5:10 am-11:55 am

1 stop6h 45m

George Town Owen Roberts Intl

Wed 7/22

12:50 pm-10:05 pm

1 stop9h 15m

$356

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 7/15

5:10 am-11:55 am

1 stop6h 45m

George Town Owen Roberts Intl

Wed 7/22

12:50 pm-11:15 pm

2 stops10h 25m

$448

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 11/13

5:10 am-12:35 pm

1 stop6h 25m

George Town Owen Roberts Intl

Mon 11/16

1:30 pm-10:40 pm

2 stops10h 10m

$480

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 6/16

5:10 am-11:55 am

1 stop6h 45m

George Town Owen Roberts Intl

Sat 6/20

1:05 pm-10:25 pm

1 stop9h 20m

$514

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 6/16

7:35 pm-11:55 am

2 stops16h 20m

George Town Owen Roberts Intl

Sat 6/20

1:05 pm-10:25 pm

1 stop9h 20m

$519

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 11/13

3:40 pm-1:00 pm

2 stops20h 20m

George Town Owen Roberts Intl

Mon 11/16

1:30 pm-10:40 pm

2 stops10h 10m

$541
Quickest round-trip

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 6/29

6:30 am-11:55 am

1 stop5h 25m

George Town Owen Roberts Intl

Mon 7/6

12:50 pm-9:25 pm

1 stop8h 35m

$551

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 6/29

6:30 am-11:55 am

1 stop5h 25m

George Town Owen Roberts Intl

Mon 7/6

12:50 pm-12:10 am

2 stops11h 20m

$556

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 11/7

3:05 pm-12:35 pm

2 stops20h 30m

George Town Owen Roberts Intl

Wed 11/11

1:30 pm-7:35 pm

1 stop7h 05m

$558

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 6/19

10:25 am-12:45 pm

1 stop26h 20m

George Town Owen Roberts Intl

Tue 6/23

1:45 pm-9:40 am

1 stop19h 55m

$571

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago Midway Airport to George Town

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to George Town?

The cheapest day to depart on your flight to George Town is on a Thursday when prices can be found for as low as $530. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to George Town for around $770.

When to book flights from Chicago Midway Airport to George Town

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to George Town according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to George Town (MDW to GCM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to George Town

Fastest flight time

5h 25m

Direct flights

None
The fastest flight from Chicago Midway Airport to George Town takes 5h 25m
There are no direct flights from Chicago Midway Airport to George Town. There are no popular flight routes from Chicago Midway Airport to George Town.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to George Town

  • How far is Chicago Midway to George Town Owen Roberts Intl by plane?

    Chicago Midway and George Town Owen Roberts Intl are 1597.9 mi apart from one another. In terms of flight time, this usually takes a little over 5h 25m.

  • When did momondo last update prices for flights from Chicago Midway Airport to George Town Owen Roberts Intl Airport?

    Prices for flights from Chicago Midway Airport to George Town Owen Roberts Intl Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Chicago Midway Airport to George Town Owen Roberts Intl Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to George Town Owen Roberts Intl Airport.

  • What documentation or ID do you need to fly to George Town Owen Roberts Intl Airport?

    The travel and health documents required for your trip to George Town Owen Roberts Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at George Town Owen Roberts Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near George Town?

Book flights to George Town if you plan to visit one of these locations
East End
West Bay

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to George Town?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to George Town for you.

Can I find flights from Chicago to George Town with flexible booking policies on momondo?

Yes. All flights to George Town from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to George Town?

momondo helps you find the best flight between Chicago and George Town by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to George Town right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to George Town flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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