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Cheap flights from George Town to Chicago from $289

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from George Town to Chicago departing on 11/28. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from George Town to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
12:25 pm - 9:00 am
GCM
-
ORD
20h 35m
1 stop
Air Canada Logo
8:40 pm - 11:30 am
ORD
-
GCM
14h 50m
1 stop
$478Air Canada
Thu, Oct 8 - Wed, Oct 14
Air Canada Logo
12:25 pm - 9:00 am
GCM
-
ORD
20h 35m
1 stop
Air Canada Logo
3:40 pm - 11:30 am
ORD
-
GCM
19h 50m
2 stops
$482Air Canada
Thu, Oct 8 - Wed, Oct 14
American Airlines Logo
12:35 pm - 11:00 pm
GCM
-
ORD
10h 25m
1 stop
American Airlines Logo
5:18 am - 11:30 am
ORD
-
GCM
6h 12m
1 stop
$591American Airlines
Thu, Oct 8 - Tue, Oct 13
American Airlines Logo
12:00 pm - 11:00 pm
GCM
-
ORD
11h 00m
2 stops
American Airlines Logo
5:18 am - 11:30 am
ORD
-
GCM
6h 12m
1 stop
$596American Airlines
Thu, Oct 8 - Tue, Oct 13
Delta Logo
1:04 pm - 10:36 pm
GCM
-
MDW
9h 32m
1 stop
Delta Logo
6:05 am - 11:39 am
MDW
-
GCM
5h 34m
1 stop
$672Delta
Tue, Aug 4 - Tue, Aug 11
Delta Logo
12:56 pm - 10:15 pm
GCM
-
MDW
9h 19m
1 stop
Delta Logo
6:42 pm - 11:39 am
MDW
-
GCM
16h 57m
2 stops
$759Delta
Sat, Aug 1 - Sat, Aug 8
Southwest Logo
1:30 pm - 10:40 pm
GCM
-
MDW
10h 10m
2 stops
Southwest Logo
7:30 pm - 12:55 pm
MDW
-
GCM
16h 25m
2 stops
$779Southwest
Thu, Dec 31 - Wed, Jan 6
Southwest Logo
1:30 pm - 10:40 pm
GCM
-
MDW
10h 10m
2 stops
Southwest Logo
5:45 am - 12:55 pm
MDW
-
GCM
6h 10m
1 stop
$811Southwest
Thu, Dec 31 - Wed, Jan 6
Multiple Airlines Logo
11:30 am - 6:33 pm
GCM
-
MDW
31h 03m
3 stops
Multiple Airlines Logo
9:24 am - 9:00 pm
MDW
-
GCM
35h 36m
3 stops
$1,264Multiple Airlines
Tue, Aug 11 - Tue, Aug 18
Multiple Airlines Logo
10:40 am - 6:25 pm
GCM
-
MDW
31h 45m
2 stops
Multiple Airlines Logo
9:59 am - 9:15 pm
MDW
-
GCM
35h 16m
3 stops
$1,568Multiple Airlines
Sat, Aug 1 - Sat, Aug 8

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American Airlines flights from George Town to Chicago

Our best American Airlines deals on George Town to Chicago flight tickets
American Airlines
Oct 8
GCM12:35 pmGeorge Town Owen Roberts Intl
10h 25m
1 stop
ORD11:00 pmChicago O'Hare Intl
Oct 13
ORD5:18 amChicago O'Hare Intl
6h 12m
1 stop
GCM11:30 amGeorge Town Owen Roberts Intl
$591
American Airlines
Oct 8
GCM12:00 pmGeorge Town Owen Roberts Intl
11h 00m
2 stops
ORD11:00 pmChicago O'Hare Intl
Oct 13
ORD5:18 amChicago O'Hare Intl
6h 12m
1 stop
GCM11:30 amGeorge Town Owen Roberts Intl
$596
American Airlines
Oct 8
GCM12:35 pmGeorge Town Owen Roberts Intl
10h 25m
1 stop
ORD11:00 pmChicago O'Hare Intl
Oct 13
ORD5:18 amChicago O'Hare Intl
6h 12m
1 stop
GCM11:30 amGeorge Town Owen Roberts Intl
$611

United Airlines flights from George Town to Chicago

Our best United Airlines deals on George Town to Chicago flight tickets
United Airlines
Aug 1
GCM1:50 pmGeorge Town Owen Roberts Intl
4h 23m
ORD6:13 pmChicago O'Hare Intl
Aug 8
ORD7:35 amChicago O'Hare Intl
8h 00m
1 stop
GCM3:35 pmGeorge Town Owen Roberts Intl
$834
United Airlines
Aug 15
GCM2:45 pmGeorge Town Owen Roberts Intl
8h 37m
1 stop
ORD11:22 pmChicago O'Hare Intl
Dec 18
ORD8:45 amChicago O'Hare Intl
4h 00m
GCM1:45 pmGeorge Town Owen Roberts Intl
$870

momondo Fare Finder

 
Customize your flight search to find flights from George Town to Chicago 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 July 6, 2026.
Use the filters below to find and compare flights from George Town to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 10/8

12:25 pm-9:00 am

1 stop20h 35m

Chicago O'Hare Intl

Wed 10/14

8:40 pm-11:30 am

1 stop14h 50m

$478

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 10/8

12:25 pm-9:00 am

1 stop20h 35m

Chicago O'Hare Intl

Wed 10/14

3:40 pm-11:30 am

2 stops19h 50m

$482

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 10/8

12:35 pm-11:00 pm

1 stop10h 25m

Chicago O'Hare Intl

Tue 10/13

5:18 am-11:30 am

1 stop6h 12m

$591

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 10/8

12:00 pm-11:00 pm

2 stops11h 00m

Chicago O'Hare Intl

Tue 10/13

5:18 am-11:30 am

1 stop6h 12m

$596
Quickest round-trip

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Tue 8/4

1:04 pm-10:36 pm

1 stop9h 32m

Chicago Midway

Tue 8/11

6:05 am-11:39 am

1 stop5h 34m

$672

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 8/1

12:56 pm-10:15 pm

1 stop9h 19m

Chicago Midway

Sat 8/8

6:42 pm-11:39 am

2 stops16h 57m

$759

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 12/31

1:30 pm-10:40 pm

2 stops10h 10m

Chicago Midway

Wed 1/6

7:30 pm-12:55 pm

2 stops16h 25m

$779

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 12/31

1:30 pm-10:40 pm

2 stops10h 10m

Chicago Midway

Wed 1/6

5:45 am-12:55 pm

1 stop6h 10m

$811

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Tue 8/11

11:30 am-6:33 pm

3 stops31h 03m

Chicago Midway

Tue 8/18

9:24 am-9:00 pm

3 stops35h 36m

$1,264

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 8/1

10:40 am-6:25 pm

2 stops31h 45m

Chicago Midway

Sat 8/8

9:59 am-9:15 pm

3 stops35h 16m

$1,568

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from George Town to Chicago

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 month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from George Town, with most prices found around $0. If you’re not able to fly to Chicago in September, then May is your next best option. Flight prices from George Town to Chicago during May average around $372.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $470. This is often the case because there is less demand to fly during this day of the week. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from George Town to Chicago for around $2,559.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from George Town to Chicago during this time can be as low as $571. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $707.

What is the cheapest George Town Owen Roberts Intl to Chicago flight route?

Fly from George Town Owen Roberts Intl to Chicago O'Hare Intl for the best George Town Owen Roberts Intl - Chicago flight prices

What cabin class options are available on George Town to Chicago flights?

There are 3 cabin classes available to choose from on George Town to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on George Town to Chicago flights?

You could potentially save up to 17% on your flight if you consider stops on a George Town to Chicago flight.

How have George Town to Chicago flight prices changed over time?

When to book flights from George Town to Chicago

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

Cheap George Town to Chicago (GCM to CHI) flight deals and tips

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

Best Price Found

$333

Fastest flight time

4h 14m

Direct flights

Wed, Thu, Fri, Sat and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from George Town in the past 72 hours is $333. The best round-trip flight deal from George Town to Chicago found on momondo in the last 72 hours is $636.
The fastest flight from George Town to Chicago takes 4h 14m
Direct flights go from George Town to Chicago on Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From George Town there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from George Town to Chicago

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

    The distance between George Town Owen Roberts Intl and Chicago is about 1602.2 mi. Typically, this will take 4h 14m by plane in normal conditions.

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

    Prices for flights from George Town Owen Roberts Intl Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from George Town Owen Roberts Intl Airport to Chicago?

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

    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 George Town Owen Roberts Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from George Town to Chicago?

  • What is the most popular airline from George Town to Chicago?

Best airlines flying from George Town to Chicago

Compare and see reviews for airlines that fly from George Town to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $389Free CancellationRating
7.1
11,782 reviews
Search American Airlines flights

Traveling to a place near Chicago?

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Saint John

Why use momondo?

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

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 George Town to Chicago for you.

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

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

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from George Town to Chicago.

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

Yes. momondo can track prices for George Town to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport