Cheap flights from Chicago Midway Airport to George Town from $202

1 adult
1 adult, Economy, 0 bags

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
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 - 10:45 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
10h 15m2 stops Orlando Nashville Intl
$514Southwest
Tue, Dec 1 - Thu, Dec 3
Southwest Logo
5:25 am - 12:55 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
6h 30m1 stop Orlando
Southwest Logo
1:50 pm - 9:05 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
8h 15m1 stop Orlando
$540Southwest
Sun, Jan 17 - Fri, Jan 22
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 - 9:55 amGCM  George Town Owen Roberts Intl-MDW Chicago Midway
21h 05m2 stops Orlando Denver Intl
$544Southwest
Sun, Jan 17 - Fri, Jan 22
Southwest Logo
5:25 am - 12:35 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
$585Southwest
Sun, Jan 3 - Thu, Jan 7
Southwest Logo
6:00 pm - 12:55 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
17h 55m2 stops Las Vegas Harry Reid Intl Orlando
Southwest Logo
1:50 pm - 11:05 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
10h 15m2 stops Orlando Baltimore/Washington
$588Southwest
Sat, Feb 6 - Thu, Feb 11
Southwest Logo
9:20 pm - 12:35 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
14h 15m2 stops Baltimore/Washington Orlando
Southwest Logo
1:50 pm - 9:05 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
8h 15m1 stop Orlando
$589Southwest
Sun, Jan 3 - Thu, Jan 7
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
$599Southwest
Mon, Dec 7 - Mon, Dec 14
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 - 9:35 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
9h 05m2 stops Orlando Lambert-St Louis
$603Southwest
Mon, Dec 7 - Mon, Dec 14
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 - 8:20 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
7h 50m2 stops Orlando Lambert-St Louis
$613Southwest
Sun, Dec 6 - Sun, Dec 13
Southwest Logo
8:50 pm - 1:00 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
15h 10m2 stops Phoenix Sky Harbor Intl Orlando
Southwest Logo
1:30 pm - 6:55 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
6h 25m1 stop Orlando
$615Southwest
Fri, Dec 4 - Fri, Dec 11

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.

Southwest flights from Chicago Midway Airport to George Town

Our best Southwest deals on Chicago Midway Airport to George Town flight tickets
Southwest
Dec 1
MDW4:10 pmChicago Midway
19h 25m
2 stops
GCM12:35 pmGeorge Town Owen Roberts Intl
Dec 3
GCM1:30 pmGeorge Town Owen Roberts Intl
10h 15m
2 stops
MDW10:45 pmChicago Midway
$514
Southwest
Jan 17
MDW5:25 amChicago Midway
6h 30m
1 stop
GCM12:55 pmGeorge Town Owen Roberts Intl
Jan 22
GCM1:50 pmGeorge Town Owen Roberts Intl
8h 15m
1 stop
MDW9:05 pmChicago Midway
$540
Southwest
Jan 17
MDW7:50 pmChicago Midway
16h 05m
2 stops
GCM12:55 pmGeorge Town Owen Roberts Intl
Jan 22
GCM1:50 pmGeorge Town Owen Roberts Intl
21h 05m
2 stops
MDW9:55 amChicago Midway
$544

Delta flights from Chicago Midway Airport to George Town

Our best Delta deals on Chicago Midway Airport to George Town flight tickets
Delta
Jan 3
MDW6:00 amChicago Midway
6h 12m
1 stop
GCM1:12 pmGeorge Town Owen Roberts Intl
Jan 13
GCM2:39 pmGeorge Town Owen Roberts Intl
8h 38m
1 stop
MDW10:17 pmChicago Midway
$658
Delta
Dec 25
MDW6:00 amChicago Midway
6h 12m
1 stop
GCM1:12 pmGeorge Town Owen Roberts Intl
Dec 30
GCM3:51 pmGeorge Town Owen Roberts Intl
7h 31m
1 stop
MDW10:22 pmChicago Midway
$698
Delta
Jan 6
MDW6:40 pmChicago Midway
17h 34m
2 stops
GCM1:14 pmGeorge Town Owen Roberts Intl
Jan 11
GCM2:39 pmGeorge Town Owen Roberts Intl
8h 38m
1 stop
MDW10:17 pmChicago Midway
$702

momondo Fare Finder

 
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 Chicago Midway - GCM George Town Owen Roberts Intl

MDWGCM

Chicago Midway

Tue 12/1

4:10 pm-12:35 pm

2 stops19h 25m

George Town Owen Roberts Intl

Thu 12/3

1:30 pm-10:45 pm

2 stops10h 15m

$514

ChicagoGeorge Town

MDW Chicago Midway - GCM George Town Owen Roberts Intl

MDWGCM

Chicago Midway

Sun 1/17

5:25 am-12:55 pm

1 stop6h 30m

George Town Owen Roberts Intl

Fri 1/22

1:50 pm-9:05 pm

1 stop8h 15m

$540

ChicagoGeorge Town

MDW Chicago Midway - GCM George Town Owen Roberts Intl

MDWGCM

Chicago Midway

Sun 1/17

7:50 pm-12:55 pm

2 stops16h 05m

George Town Owen Roberts Intl

Fri 1/22

1:50 pm-9:55 am

2 stops21h 05m

$544

ChicagoGeorge Town

MDW Chicago Midway - GCM George Town Owen Roberts Intl

MDWGCM

Chicago Midway

Sun 1/3

5:25 am-12:35 pm

1 stop6h 10m

George Town Owen Roberts Intl

Thu 1/7

1:50 pm-10:55 pm

1 stop10h 05m

$585

ChicagoGeorge Town

MDW Chicago Midway - GCM George Town Owen Roberts Intl

MDWGCM

Chicago Midway

Sat 2/6

6:00 pm-12:55 pm

2 stops17h 55m

George Town Owen Roberts Intl

Thu 2/11

1:50 pm-11:05 pm

2 stops10h 15m

$588

ChicagoGeorge Town

MDW Chicago Midway - GCM George Town Owen Roberts Intl

MDWGCM

Chicago Midway

Sun 1/3

9:20 pm-12:35 pm

2 stops14h 15m

George Town Owen Roberts Intl

Thu 1/7

1:50 pm-9:05 pm

1 stop8h 15m

$589

ChicagoGeorge Town

MDW Chicago Midway - GCM George Town Owen Roberts Intl

MDWGCM

Chicago Midway

Mon 12/7

5:20 am-12:35 pm

1 stop6h 15m

George Town Owen Roberts Intl

Mon 12/14

1:30 pm-9:20 pm

1 stop8h 50m

$599

ChicagoGeorge Town

MDW Chicago Midway - GCM George Town Owen Roberts Intl

MDWGCM

Chicago Midway

Mon 12/7

5:20 am-12:35 pm

1 stop6h 15m

George Town Owen Roberts Intl

Mon 12/14

1:30 pm-9:35 pm

2 stops9h 05m

$603
Quickest round-trip

ChicagoGeorge Town

MDW Chicago Midway - GCM George Town Owen Roberts Intl

MDWGCM

Chicago Midway

Sun 12/6

5:10 am-12:35 pm

1 stop6h 25m

George Town Owen Roberts Intl

Sun 12/13

1:30 pm-8:20 pm

2 stops7h 50m

$613

ChicagoGeorge Town

MDW Chicago Midway - GCM George Town Owen Roberts Intl

MDWGCM

Chicago Midway

Fri 12/4

8:50 pm-1:00 pm

2 stops15h 10m

George Town Owen Roberts Intl

Fri 12/11

1:30 pm-6:55 pm

1 stop6h 25m

$615

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 $622. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to George Town for around $734.

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

Best Price Found

$202

Fastest flight time

5h 43m

Direct flights

None
The best one-way flight to George Town from Chicago Midway Airport in the past 72 hours is $202. The best round-trip flight deal from Chicago Midway Airport to George Town found on momondo in the last 72 hours is $514.
The fastest flight from Chicago Midway Airport to George Town takes 5h 43m
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.

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 43m.

  • 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
West Bay
East End

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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 12/10
Thu 12/17

Find better results for your trip to the Cayman Islands