Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to George Town from $138

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 to George Town departing on 10/4. 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 Chicago to George Town

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
5:35 pm - 9:45 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
16h 10m1 stop Toronto Pearson Intl
Air Canada Logo
12:25 pm - 2:50 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
26h 25m1 stop Toronto Pearson Intl
$335Air Canada
Fri, Sep 11 - Thu, Sep 17
Air Canada Logo
9:50 am - 11:30 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
25h 40m1 stop Toronto Pearson Intl
Air Canada Logo
12:10 pm - 6:43 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
30h 33m1 stop Toronto Pearson Intl
$346Air Canada
Wed, Oct 21 - Sat, Oct 31
Air Canada Logo
3:45 pm - 11:30 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
19h 45m1 stop Toronto Pearson Intl
Air Canada Logo
12:10 pm - 8:13 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
8h 03m1 stop Toronto Pearson Intl
$346Air Canada
Fri, Oct 16 - Sun, Oct 25
Air Canada Logo
5:35 pm - 11:30 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
17h 55m1 stop Toronto Pearson Intl
Air Canada Logo
12:10 pm - 11:07 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
22h 57m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
$349Air Canada
Fri, Oct 16 - Sun, Oct 25
American Airlines Logo
9:31 am - 2:35 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 04mnonstop
American Airlines Logo
3:25 pm - 6:49 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 24mnonstop
$597American Airlines
Tue, Feb 2 - Wed, Feb 10
American Airlines Logo
6:59 am - 8:23 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
12h 24m1 stop Miami
American Airlines Logo
3:25 pm - 6:49 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 24mnonstop
$601American Airlines
Tue, Feb 2 - Wed, Feb 10
American Airlines Logo
5:05 am - 8:23 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
14h 18m1 stop Miami
American Airlines Logo
12:55 pm - 7:51 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
7h 56m1 stop Charlotte Douglas
$611American Airlines
Tue, Feb 2 - Wed, Feb 10
United Airlines Logo
8:45 am - 1:45 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 00mnonstop
United Airlines Logo
2:50 pm - 6:04 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 14mnonstop
$617United Airlines
Sun, Jan 17 - Fri, Jan 22
United Airlines Logo
5:00 am - 1:15 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
7h 15m1 stop Newark
United Airlines Logo
2:50 pm - 6:04 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 14mnonstop
$621United Airlines
Sun, Jan 24 - Fri, Jan 29
United Airlines Logo
5:00 am - 1:15 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
7h 15m1 stop Newark
United Airlines Logo
2:50 pm - 6:04 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 14mnonstop
$621United Airlines
Sun, Jan 17 - Fri, Jan 22

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

Southwest flights from Chicago to George Town

Our best Southwest deals on Chicago to George Town flight tickets
Southwest
Nov 3
MDW5:20 amChicago Midway
6h 15m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
Nov 12
GCM1:30 pmGeorge Town Owen Roberts Intl
6h 25m
1 stop
MDW6:55 pmChicago Midway
$474
Southwest
Nov 3
MDW5:20 amChicago Midway
6h 15m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
Nov 12
GCM1:30 pmGeorge Town Owen Roberts Intl
8h 05m
1 stop
MDW8:35 pmChicago Midway
$477
Southwest
Feb 2
MDW7:55 pmChicago Midway
16h 00m
2 stops
GCM12:55 pmGeorge Town Owen Roberts Intl
Feb 10
GCM1:50 pmGeorge Town Owen Roberts Intl
21h 35m
2 stops
MDW10:25 amChicago Midway
$479

Air Canada flights from Chicago to George Town

Our best Air Canada deals on Chicago to George Town flight tickets
Air Canada
Oct 16
ORD3:45 pmChicago O'Hare Intl
19h 45m
1 stop
GCM11:30 amGeorge Town Owen Roberts Intl
Oct 25
GCM12:10 pmGeorge Town Owen Roberts Intl
8h 03m
1 stop
ORD8:13 pmChicago O'Hare Intl
$346
Air Canada
Oct 16
ORD5:35 pmChicago O'Hare Intl
17h 55m
1 stop
GCM11:30 amGeorge Town Owen Roberts Intl
Oct 25
GCM12:10 pmGeorge Town Owen Roberts Intl
22h 57m
2 stops
ORD11:07 amChicago O'Hare Intl
$349
Air Canada
Sep 11
ORD8:40 pmChicago O'Hare Intl
13h 05m
1 stop
GCM9:45 amGeorge Town Owen Roberts Intl
Sep 17
GCM12:25 pmGeorge Town Owen Roberts Intl
19h 35m
1 stop
ORD8:00 amChicago O'Hare Intl
$351

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 August 9, 2026.
Use the filters below to find and compare flights from Chicago to George Town that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Fri 9/11

5:35 pm-9:45 am

1 stop16h 10m

George Town Owen Roberts Intl

Thu 9/17

12:25 pm-2:50 pm

1 stop26h 25m

$335

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Wed 10/21

9:50 am-11:30 am

1 stop25h 40m

George Town Owen Roberts Intl

Sat 10/31

12:10 pm-6:43 pm

1 stop30h 33m

$346

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Fri 10/16

3:45 pm-11:30 am

1 stop19h 45m

George Town Owen Roberts Intl

Sun 10/25

12:10 pm-8:13 pm

1 stop8h 03m

$346

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Fri 10/16

5:35 pm-11:30 am

1 stop17h 55m

George Town Owen Roberts Intl

Sun 10/25

12:10 pm-11:07 am

2 stops22h 57m

$349

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Tue 2/2

9:31 am-2:35 pm

Nonstop4h 04m

George Town Owen Roberts Intl

Wed 2/10

3:25 pm-6:49 pm

Nonstop4h 24m

$597

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Tue 2/2

6:59 am-8:23 pm

1 stop12h 24m

George Town Owen Roberts Intl

Wed 2/10

3:25 pm-6:49 pm

Nonstop4h 24m

$601

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Tue 2/2

5:05 am-8:23 pm

1 stop14h 18m

George Town Owen Roberts Intl

Wed 2/10

12:55 pm-7:51 pm

1 stop7h 56m

$611
Quickest round-trip

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Sun 1/17

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Fri 1/22

2:50 pm-6:04 pm

Nonstop4h 14m

$617

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Sun 1/24

5:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Fri 1/29

2:50 pm-6:04 pm

Nonstop4h 14m

$621

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Sun 1/17

5:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Fri 1/22

2:50 pm-6:04 pm

Nonstop4h 14m

$621

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 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 typical price of a round-trip flight between Chicago and George Town?

Prices are currently low for flights on this route.

Typical prices usually range from $666 to $759.
The lowest price recently found on this route was $346.

What is the cheapest month to fly to George Town?

In general, February is the cheapest month to fly from Chicago to George Town. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $527. The month of January is another great option to travel to George Town, with average flight prices from Chicago averaging around $555.

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 to George Town for around $731.

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

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

How far in advance should I book a flight from Chicago to George Town?

You are more likely to see cheaper flights to George Town from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to George Town for around $690 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to George Town from Chicago for as low as $492 on momondo.

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

There are 3 cabin classes available to choose from on Chicago to George Town 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 Chicago to George Town flights?

You could potentially save up to 10% on your flight if you consider stops on a Chicago to George Town flight.

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

When to book flights from Chicago to George Town

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

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

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

Best Price Found

$751

Fastest flight time

4h 00m

Direct flights

Every day

Airports in George Town

1 airport
The best flight deal from Chicago to George Town found on momondo in the last 72 hours is $751
The fastest flight from Chicago to George Town takes 4h 00m
Direct flights go from Chicago to George Town every day.
There is 1 airport in George Town. From Chicago there are direct flights to George Town Owen Roberts Intl (GCM).
Search flight deals

Frequently asked questions about flying from Chicago to George Town

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

    George Town Owen Roberts Intl is 1602.2 mi away from Chicago. Flights usually cover this in 4h 00m, depending on flying conditions and air traffic around both airports.

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to George Town Owen Roberts Intl Airport.

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

    The required travel and health documents for your George Town Owen Roberts Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at George Town Owen Roberts Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

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

Best airlines flying from Chicago to George Town

Compare and see reviews for airlines that fly from Chicago to George Town with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $341Free CancellationRating
7.4
10,085 reviews
Search United Airlines flights
American AirlinesPriceFrom $438Free CancellationRating
7.1
11,885 reviews
Search American Airlines flights

  • United Airlines Flights From Chicago to George Town

    The lowest priced United Airlines flight from Chicago to George Town from the last 72 hours was $341. Generally, United Airlines has 1 flight on this route every week with an average price of $613. United Airlines is rated 7.4/10 by our users.

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?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to George Town. momondo saves you time and could save you money on your trip.

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?

If you are simply researching potential flights to George Town, momondo offers a useful price alert feature which will track prices for flights to George Town from Chicago and alert you when they change.

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
Tue 9/8
Tue 9/15
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the Cayman Islands