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Cheap flights from the Cayman Islands to Chicago from $262

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 9/17. 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 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
5:35 pm - 11:30 am
ORD
-
GCM
17h 55m
1 stop
$425Air 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
43h 50m
2 stops
$428Air Canada
Thu, Sep 24 - Sat, Sep 26
Air Canada Logo
12:25 pm - 2:52 pm
GCM
-
ORD
26h 27m
2 stops
Air Canada Logo
3:40 pm - 11:30 am
ORD
-
GCM
43h 50m
2 stops
$431Air Canada
Thu, Sep 24 - Sat, Sep 26
American Airlines Logo
12:40 pm - 11:53 pm
GCM
-
ORD
11h 13m
1 stop
American Airlines Logo
5:22 am - 11:00 am
ORD
-
GCM
5h 38m
1 stop
$611American Airlines
Wed, Oct 7 - Mon, Oct 12
American Airlines Logo
1:25 pm - 11:21 pm
GCM
-
ORD
9h 56m
2 stops
American Airlines Logo
5:22 am - 11:00 am
ORD
-
GCM
5h 38m
1 stop
$616American Airlines
Wed, Oct 7 - Mon, Oct 12
Southwest Logo
12:50 pm - 8:10 pm
GCM
-
MDW
7h 20m
1 stop
Southwest Logo
5:10 am - 11:55 am
MDW
-
GCM
6h 45m
1 stop
$631Southwest
Wed, Jul 15 - Wed, Jul 22
Multiple Airlines Logo
7:00 am - 10:03 pm
GCM
-
MDW
15h 03m
2 stops
Multiple Airlines Logo
6:05 am - 9:15 pm
MDW
-
GCM
15h 10m
2 stops
$653Multiple Airlines
Mon, Aug 3 - Mon, Aug 10
Southwest Logo
12:50 pm - 8:10 pm
GCM
-
MDW
7h 20m
1 stop
Southwest Logo
5:25 pm - 11:55 am
MDW
-
GCM
18h 30m
2 stops
$656Southwest
Wed, Jul 15 - Wed, Jul 22
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
$682Delta
Mon, Aug 3 - Mon, Aug 10
Multiple Airlines Logo
7:00 am - 6:25 pm
GCM
-
MDW
35h 25m
3 stops
Multiple Airlines Logo
9:54 am - 11:25 am
MDW
-
GCM
25h 31m
3 stops
$1,279Multiple Airlines
Wed, Jul 15 - Wed, Jul 22

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Air Canada flights from Cayman Islands to Chicago

Our best Air Canada deals on Cayman Islands to Chicago flight tickets
Air Canada
Oct 8
GCM12:25 pmGeorge Town Owen Roberts Intl
20h 35m
1 stop
ORD9:00 amChicago O'Hare Intl
Oct 14
ORD5:35 pmChicago O'Hare Intl
17h 55m
1 stop
GCM11:30 amGeorge Town Owen Roberts Intl
$425
Air Canada
Sep 24
GCM12:25 pmGeorge Town Owen Roberts Intl
20h 35m
1 stop
ORD9:00 amChicago O'Hare Intl
Sep 26
ORD3:40 pmChicago O'Hare Intl
43h 50m
2 stops
GCM11:30 amGeorge Town Owen Roberts Intl
$428
Air Canada
Sep 24
GCM12:25 pmGeorge Town Owen Roberts Intl
26h 27m
2 stops
ORD2:52 pmChicago O'Hare Intl
Sep 26
ORD3:40 pmChicago O'Hare Intl
43h 50m
2 stops
GCM11:30 amGeorge Town Owen Roberts Intl
$431

American Airlines flights from Cayman Islands to Chicago

Our best American Airlines deals on Cayman Islands to Chicago flight tickets
American Airlines
Oct 8
GCM12:40 pmGeorge Town Owen Roberts Intl
11h 13m
1 stop
ORD11:53 pmChicago O'Hare Intl
Oct 13
ORD5:22 amChicago O'Hare Intl
5h 38m
1 stop
GCM11:00 amGeorge Town Owen Roberts Intl
$611
American Airlines
Oct 7
GCM1:25 pmGeorge Town Owen Roberts Intl
9h 56m
2 stops
ORD11:21 pmChicago O'Hare Intl
Oct 12
ORD5:22 amChicago O'Hare Intl
5h 38m
1 stop
GCM11:00 amGeorge Town Owen Roberts Intl
$616
American Airlines
Aug 3
GCM12:02 pmGeorge Town Owen Roberts Intl
11h 28m
2 stops
ORD11:30 pmChicago O'Hare Intl
Aug 10
ORD8:53 pmChicago O'Hare Intl
14h 34m
1 stop
GCM11:27 amGeorge Town Owen Roberts Intl
$669

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 June 23, 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

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

5:35 pm-11:30 am

1 stop17h 55m

$425

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 9/24

12:25 pm-9:00 am

1 stop20h 35m

Chicago O'Hare Intl

Sat 9/26

3:40 pm-11:30 am

2 stops43h 50m

$428

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 9/24

12:25 pm-2:52 pm

2 stops26h 27m

Chicago O'Hare Intl

Sat 9/26

3:40 pm-11:30 am

2 stops43h 50m

$431

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 10/7

12:40 pm-11:53 pm

1 stop11h 13m

Chicago O'Hare Intl

Mon 10/12

5:22 am-11:00 am

1 stop5h 38m

$611

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 10/7

1:25 pm-11:21 pm

2 stops9h 56m

Chicago O'Hare Intl

Mon 10/12

5:22 am-11:00 am

1 stop5h 38m

$616
Quickest round-trip

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Wed 7/15

12:50 pm-8:10 pm

1 stop7h 20m

Chicago Midway

Wed 7/22

5:10 am-11:55 am

1 stop6h 45m

$631

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 8/3

7:00 am-10:03 pm

2 stops15h 03m

Chicago Midway

Mon 8/10

6:05 am-9:15 pm

2 stops15h 10m

$653

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Wed 7/15

12:50 pm-8:10 pm

1 stop7h 20m

Chicago Midway

Wed 7/22

5:25 pm-11:55 am

2 stops18h 30m

$656

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 8/3

1:04 pm-10:36 pm

1 stop9h 32m

Chicago Midway

Mon 8/10

6:05 am-11:39 am

1 stop5h 34m

$682

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Wed 7/15

7:00 am-6:25 pm

3 stops35h 25m

Chicago Midway

Wed 7/22

9:54 am-11:25 am

3 stops25h 31m

$1,279

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 month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Cayman Islands, 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 Cayman Islands 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 Cayman Islands 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 Cayman Islands 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 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 17% 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

Fri 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 Friday 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

Frequently asked questions about flying from the Cayman Islands to Chicago

  • 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 many operators does momondo search for flights from Cayman Islands to Chicago?

  • 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?

Best airlines flying from Cayman Islands to Chicago

Compare and see reviews for airlines that fly from Cayman Islands to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $389Free CancellationRating
7.1
11,741 reviews
Search American Airlines flights

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
Portage
Saint Joseph
Lansing
Valparaiso
Schererville
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