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Cheap flights from the Cayman Islands to Chicago from $163

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from the Cayman Islands to Chicago departing on 2/7. 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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Find the cheapest flights from the Cayman Islands to Chicago

Recent round-trip flight deals from the Cayman Islands to Chicago

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
8:20 pm - 11:30 am
ORD
-
GCM
15h 10m
1 stop
$321Air Canada
Thu, Jun 11 - Sun, Jun 14
Multiple Airlines Logo
11:30 am - 9:39 am
GCM
-
ORD
23h 09m
1 stop
Multiple Airlines Logo
4:43 pm - 1:43 pm
ORD
-
GCM
20h 00m
1 stop
$329Multiple Airlines
Wed, Feb 25 - Wed, Mar 4
Multiple Airlines Logo
11:30 am - 8:18 am
GCM
-
ORD
21h 48m
1 stop
Multiple Airlines Logo
9:18 am - 4:05 pm
ORD
-
GCM
29h 47m
1 stop
$355Multiple Airlines
Tue, Feb 10 - Tue, Feb 17
Multiple Airlines Logo
11:30 am - 7:54 am
GCM
-
ORD
21h 24m
2 stops
Multiple Airlines Logo
4:43 pm - 1:43 pm
ORD
-
GCM
20h 00m
1 stop
$357Multiple Airlines
Wed, Feb 25 - Wed, Mar 4
Air Canada Logo
1:30 pm - 6:55 pm
GCM
-
ORD
30h 25m
2 stops
Air Canada Logo
6:04 pm - 12:25 pm
ORD
-
GCM
41h 21m
2 stops
$405Air Canada
Tue, Feb 10 - Tue, Feb 17
American Airlines Logo
8:50 am - 11:08 pm
GCM
-
ORD
15h 18m
1 stop
American Airlines Logo
9:36 am - 2:35 pm
ORD
-
GCM
3h 59mnonstop
$449American Airlines
Tue, Feb 10 - Tue, Feb 17
Delta Logo
1:54 pm - 10:31 pm
GCM
-
MDW
9h 37m
1 stop
Delta Logo
6:00 am - 12:29 pm
MDW
-
GCM
5h 29m
1 stop
$474Delta
Sat, Feb 21 - Wed, Feb 25
Delta Logo
1:54 pm - 10:31 pm
GCM
-
MDW
9h 37m
1 stop
Delta Logo
6:00 am - 12:29 pm
MDW
-
GCM
5h 29m
1 stop
$523Delta
Wed, Feb 25 - Wed, Mar 4
Southwest Logo
12:45 pm - 11:55 pm
GCM
-
MDW
11h 10m
2 stops
Southwest Logo
8:40 pm - 11:50 am
MDW
-
GCM
15h 10m
2 stops
$602Southwest
Thu, Jun 11 - Sun, Jun 14
Southwest Logo
12:45 pm - 9:20 pm
GCM
-
MDW
8h 35m
1 stop
Southwest Logo
5:20 am - 11:50 am
MDW
-
GCM
6h 30m
1 stop
$647Southwest
Thu, Jun 11 - Sun, Jun 14

American Airlines flights from Cayman Islands to Chicago

Our best American Airlines deals on Cayman Islands to Chicago flight tickets
American Airlines
Feb 10
GCM8:50 amGeorge Town Owen Roberts Intl
15h 18m
1 stop
ORD11:08 pmChicago O'Hare Intl
Feb 17
ORD9:36 amChicago O'Hare Intl
3h 59m
GCM2:35 pmGeorge Town Owen Roberts Intl
$449
American Airlines
Jan 22
GCM12:50 pmGeorge Town Owen Roberts Intl
7h 32m
1 stop
ORD7:22 pmChicago O'Hare Intl
Jan 26
ORD9:31 amChicago O'Hare Intl
4h 04m
GCM2:35 pmGeorge Town Owen Roberts Intl
$509
American Airlines
Feb 21
GCM4:00 pmGeorge Town Owen Roberts Intl
4h 20m
ORD7:20 pmChicago O'Hare Intl
Feb 25
ORD9:36 amChicago O'Hare Intl
3h 59m
GCM2:35 pmGeorge Town Owen Roberts Intl
$568

Air Canada flights from Cayman Islands to Chicago

Our best Air Canada deals on Cayman Islands to Chicago flight tickets
Air Canada
Jun 11
GCM12:25 pmGeorge Town Owen Roberts Intl
20h 35m
1 stop
ORD9:00 amChicago O'Hare Intl
Jun 14
ORD8:20 pmChicago O'Hare Intl
15h 10m
1 stop
GCM11:30 amGeorge Town Owen Roberts Intl
$321
Air Canada
Jun 11
GCM12:25 pmGeorge Town Owen Roberts Intl
19h 40m
2 stops
ORD8:05 amChicago O'Hare Intl
Jun 14
ORD8:20 pmChicago O'Hare Intl
15h 10m
1 stop
GCM11:30 amGeorge Town Owen Roberts Intl
$329
Air Canada
Feb 10
GCM1:30 pmGeorge Town Owen Roberts Intl
30h 25m
2 stops
ORD6:55 pmChicago O'Hare Intl
Feb 17
ORD6:04 pmChicago O'Hare Intl
41h 21m
2 stops
GCM12:25 pmGeorge Town Owen Roberts Intl
$405

momondo Fare Finder

 
Customize your flight search to find flights from Cayman Islands 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 January 13, 2026.
Use the filters below to find and compare flights from the Cayman Islands to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 6/11

12:25 pm-9:00 am

1 stop20h 35m

Chicago O'Hare Intl

Sun 6/14

8:20 pm-11:30 am

1 stop15h 10m

$321

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 2/25

11:30 am-9:39 am

1 stop23h 09m

Chicago O'Hare Intl

Wed 3/4

4:43 pm-1:43 pm

1 stop20h 00m

$329

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 2/10

11:30 am-8:18 am

1 stop21h 48m

Chicago O'Hare Intl

Tue 2/17

9:18 am-4:05 pm

1 stop29h 47m

$355

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 2/25

11:30 am-7:54 am

2 stops21h 24m

Chicago O'Hare Intl

Wed 3/4

4:43 pm-1:43 pm

1 stop20h 00m

$357

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 2/10

1:30 pm-6:55 pm

2 stops30h 25m

Chicago O'Hare Intl

Tue 2/17

6:04 pm-12:25 pm

2 stops41h 21m

$405

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 2/10

8:50 am-11:08 pm

1 stop15h 18m

Chicago O'Hare Intl

Tue 2/17

9:36 am-2:35 pm

Nonstop3h 59m

$449

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 2/21

1:54 pm-10:31 pm

1 stop9h 37m

Chicago Midway

Wed 2/25

6:00 am-12:29 pm

1 stop5h 29m

$474

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Wed 2/25

1:54 pm-10:31 pm

1 stop9h 37m

Chicago Midway

Wed 3/4

6:00 am-12:29 pm

1 stop5h 29m

$523

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 6/11

12:45 pm-11:55 pm

2 stops11h 10m

Chicago Midway

Sun 6/14

8:40 pm-11:50 am

2 stops15h 10m

$602

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 6/11

12:45 pm-9:20 pm

1 stop8h 35m

Chicago Midway

Sun 6/14

5:20 am-11:50 am

1 stop6h 30m

$647

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 Cayman Islands 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 day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Sunday when prices can be found for as low as $373. This is often the case because there is less demand to fly during this day of the week. When flying out on a Wednesday, the most expensive travel day of the week, you can expect to see flight prices from Cayman Islands to Chicago for around $1,867.

What is the cheapest Cayman Islands to Chicago flight route?

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

What cabin class options are available on Cayman Islands to Chicago flights?

There are 2 cabin classes available to choose from on Cayman Islands 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 Cayman Islands to Chicago flights?

You could potentially save up to 36% on your flight if you consider stops on a Cayman Islands to Chicago flight.

Cheap Cayman Islands to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Cayman Islands to Chicago

Fastest flight time

4h 14m

Direct flights

Mon, Fri, Sat and Sun

Airports in Chicago

3 airports
The fastest flight from Cayman Islands to Chicago takes 4h 14m
Direct flights go from Cayman Islands to Chicago on Monday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From Cayman Islands there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

  • When did momondo last update prices for flights from Cayman Islands to Chicago?

    Prices for flights from Cayman Islands to Chicago are refreshed on a daily basis.

  • How old do you have to be to fly from Cayman Islands to Chicago?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Cayman Islands 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 Cayman Islands to Chicago?

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Cayman Islands to Chicago?

Finding the right flight to Chicago from Cayman Islands is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Cayman Islands to Chicago with flexible booking policies on momondo?

Flights from Cayman Islands to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Cayman Islands 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 Cayman Islands to Chicago.

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

Yes. momondo can track prices for Cayman Islands 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