Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Chicago Midway Airport to George Town from $209

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 5/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
6:00 am - 12:10 pm
MDW
-
GCM
6h 10m
1 stop
Southwest Logo
1:05 pm - 12:15 am
GCM
-
MDW
11h 10m
1 stop
$492Southwest
Tue, May 5 - Fri, May 8
Southwest Logo
6:00 am - 12:10 pm
MDW
-
GCM
6h 10m
1 stop
Southwest Logo
1:05 pm - 11:55 pm
GCM
-
MDW
10h 50m
2 stops
$511Southwest
Tue, May 5 - Fri, May 8
Multiple Airlines Logo
6:00 am - 9:15 pm
MDW
-
GCM
15h 15m
2 stops
Multiple Airlines Logo
7:00 am - 10:11 pm
GCM
-
MDW
15h 11m
2 stops
$523Multiple Airlines
Thu, Jun 4 - Thu, Jun 11
Southwest Logo
8:50 pm - 12:10 pm
MDW
-
GCM
15h 20m
2 stops
Southwest Logo
1:05 pm - 10:50 pm
GCM
-
MDW
9h 45m
2 stops
$542Southwest
Tue, May 5 - Fri, May 8
Delta Logo
6:05 am - 11:34 am
MDW
-
GCM
5h 29m
1 stop
Delta Logo
12:59 pm - 10:17 pm
GCM
-
MDW
9h 18m
1 stop
$553Delta
Sun, Jun 7 - Fri, Jun 12
Multiple Airlines Logo
3:20 pm - 12:45 pm
MDW
-
GCM
21h 25m
1 stop
Multiple Airlines Logo
4:45 pm - 10:11 pm
GCM
-
MDW
29h 26m
2 stops
$561Multiple Airlines
Mon, Jul 20 - Mon, Jul 27
Delta Logo
6:05 am - 11:34 am
MDW
-
GCM
5h 29m
1 stop
Delta Logo
12:59 pm - 10:17 pm
GCM
-
MDW
9h 18m
1 stop
$573Delta
Sun, Jun 7 - Fri, Jun 12
Southwest Logo
6:00 am - 12:10 pm
MDW
-
GCM
6h 10m
1 stop
Southwest Logo
1:05 pm - 12:15 am
GCM
-
MDW
11h 10m
1 stop
$579Southwest
Tue, May 12 - Mon, May 18
Multiple Airlines Logo
6:00 am - 9:15 pm
MDW
-
GCM
15h 15m
2 stops
Multiple Airlines Logo
1:45 pm - 9:40 am
GCM
-
MDW
19h 55m
1 stop
$583Multiple Airlines
Mon, Jun 8 - Sat, Jun 13
Southwest Logo
6:00 am - 12:10 pm
MDW
-
GCM
6h 10m
1 stop
Southwest Logo
1:05 pm - 12:15 am
GCM
-
MDW
11h 10m
1 stop
$584Southwest
Tue, May 5 - Thu, May 7

Delta flights from Chicago Midway Airport to George Town

Our best Delta deals on Chicago Midway Airport to George Town flight tickets
Delta
Jun 7
MDW6:05 amChicago Midway
5h 29m
1 stop
GCM11:34 amGeorge Town Owen Roberts Intl
Jun 12
GCM12:59 pmGeorge Town Owen Roberts Intl
9h 18m
1 stop
MDW10:17 pmChicago Midway
$553
Delta
Jun 7
MDW6:05 amChicago Midway
5h 29m
1 stop
GCM11:34 amGeorge Town Owen Roberts Intl
Jun 12
GCM12:59 pmGeorge Town Owen Roberts Intl
9h 18m
1 stop
MDW10:17 pmChicago Midway
$573
Delta
Aug 16
MDW6:00 amChicago Midway
5h 41m
1 stop
GCM11:41 amGeorge Town Owen Roberts Intl
Aug 27
GCM12:56 pmGeorge Town Owen Roberts Intl
19h 46m
2 stops
MDW8:42 amChicago Midway
$602

Southwest flights from Chicago Midway Airport to George Town

Our best Southwest deals on Chicago Midway Airport to George Town flight tickets
Southwest
May 5
MDW6:00 amChicago Midway
6h 10m
1 stop
GCM12:10 pmGeorge Town Owen Roberts Intl
May 8
GCM1:05 pmGeorge Town Owen Roberts Intl
11h 10m
1 stop
MDW12:15 amChicago Midway
$492
Southwest
May 5
MDW6:00 amChicago Midway
6h 10m
1 stop
GCM12:10 pmGeorge Town Owen Roberts Intl
May 8
GCM1:05 pmGeorge Town Owen Roberts Intl
10h 50m
2 stops
MDW11:55 pmChicago Midway
$511
Southwest
May 5
MDW8:50 pmChicago Midway
15h 20m
2 stops
GCM12:10 pmGeorge Town Owen Roberts Intl
May 8
GCM1:05 pmGeorge Town Owen Roberts Intl
9h 45m
2 stops
MDW10:50 pmChicago Midway
$542

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 April 17, 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

Tue 5/5

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

Fri 5/8

1:05 pm-12:15 am

1 stop11h 10m

$492

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 5/5

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

Fri 5/8

1:05 pm-11:55 pm

2 stops10h 50m

$511

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 6/4

6:00 am-9:15 pm

2 stops15h 15m

George Town Owen Roberts Intl

Thu 6/11

7:00 am-10:11 pm

2 stops15h 11m

$523

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 5/5

8:50 pm-12:10 pm

2 stops15h 20m

George Town Owen Roberts Intl

Fri 5/8

1:05 pm-10:50 pm

2 stops9h 45m

$542
Quickest round-trip

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 6/7

6:05 am-11:34 am

1 stop5h 29m

George Town Owen Roberts Intl

Fri 6/12

12:59 pm-10:17 pm

1 stop9h 18m

$553

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 7/20

3:20 pm-12:45 pm

1 stop21h 25m

George Town Owen Roberts Intl

Mon 7/27

4:45 pm-10:11 pm

2 stops29h 26m

$561

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 6/7

6:05 am-11:34 am

1 stop5h 29m

George Town Owen Roberts Intl

Fri 6/12

12:59 pm-10:17 pm

1 stop9h 18m

$573

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 5/12

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

Mon 5/18

1:05 pm-12:15 am

1 stop11h 10m

$579

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 6/8

6:00 am-9:15 pm

2 stops15h 15m

George Town Owen Roberts Intl

Sat 6/13

1:45 pm-9:40 am

1 stop19h 55m

$583

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 5/5

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

Thu 5/7

1:05 pm-12:15 am

1 stop11h 10m

$584

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 resultsSorted by cheapest first
1
2

See travel insights to George Town from

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 Wednesday 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 29m

Direct flights

None
The fastest flight from Chicago Midway Airport to George Town takes 5h 29m
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 29m.

  • 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.

An easier way to manage your George Town trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sun 5/17
Sun 5/24
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the Cayman Islands