Cheap flights from the Cayman Islands to Illinois from $264

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 Illinois departing on 1/14. 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 Illinois

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

Southwest Logo
1:30 pm - 9:50 pmGCM-ORD
9h 20m1 stop
Southwest Logo
6:05 am - 12:35 pmORD-GCM
5h 30m1 stop
$410Southwest
Find Deal
Fri, Nov 14 - Sun, Nov 16
Air Canada Logo
12:50 pm - 9:51 amGCM-ORD
45h 01m2 stops
Air Canada Logo
6:00 pm - 11:55 amORD-GCM
41h 55m2 stops
$447Air Canada
Find Deal
Thu, Oct 16 - Sat, Oct 18
Air Canada Logo
12:50 pm - 9:51 amGCM-ORD
21h 01m2 stops
Air Canada Logo
3:35 pm - 11:55 amORD-GCM
20h 20m2 stops
$450Air Canada
Find Deal
Thu, Oct 16 - Sun, Oct 19
Air Canada Logo
12:50 pm - 5:33 pmGCM-ORD
28h 43m1 stop
Air Canada Logo
6:06 pm - 11:55 amORD-GCM
41h 49m2 stops
$466Air Canada
Find Deal
Thu, Oct 16 - Sat, Oct 18
Delta Logo
12:52 pm - 9:36 pmGCM-MDW
8h 44m1 stop
Delta Logo
6:00 am - 11:36 amMDW-GCM
5h 36m1 stop
$468Delta
Find Deal
Fri, Sep 12 - Fri, Sep 19
Delta Logo
12:52 pm - 11:54 pmGCM-ORD
11h 02m1 stop
Delta Logo
5:30 am - 11:36 amORD-GCM
6h 06m1 stop
$468Delta
Find Deal
Fri, Sep 12 - Fri, Sep 19
American Airlines Logo
12:25 pm - 11:48 pmGCM-ORD
11h 23m2 stops
American Airlines Logo
8:30 pm - 11:10 amORD-GCM
14h 40m2 stops
$481American Airlines
Find Deal
Fri, Sep 12 - Fri, Sep 19
 Logo
4:45 pm - 9:22 amGCM-ORD
16h 37m1 stop
 Logo
10:27 am - 9:20 pmORD-GCM
10h 53m1 stop
Mon, Aug 18 - Fri, Aug 22
 Logo
4:45 pm - 9:22 amGCM-ORD
16h 37m1 stop
 Logo
5:21 pm - 5:20 pmORD-GCM
23h 59m1 stop
Mon, Aug 18 - Wed, Aug 20
American Airlines Logo
12:10 pm - 11:49 pmGCM-ORD
11h 39m1 stop
American Airlines Logo
11:57 am - 7:51 pmORD-GCM
6h 54m1 stop
$511American Airlines
Find Deal
Thu, Sep 4 - Thu, Dec 4

Southwest flights from Cayman Islands to Illinois

Our best Southwest deals on Cayman Islands to Illinois flight tickets
Southwest
Nov 14
GCM1:30 pmGeorge Town Owen Roberts Intl
9h 20m
1 stop
ORD9:50 pmChicago O'Hare Intl
Nov 16
ORD6:05 amChicago O'Hare Intl
5h 30m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
Southwest
Nov 14
GCM1:30 pmGeorge Town Owen Roberts Intl
9h 20m
1 stop
ORD9:50 pmChicago O'Hare Intl
Nov 16
ORD4:25 pmChicago O'Hare Intl
19h 10m
2 stops
GCM12:35 pmGeorge Town Owen Roberts Intl
Southwest
Nov 14
GCM1:30 pmGeorge Town Owen Roberts Intl
11h 00m
2 stops
MDW11:30 pmChicago Midway
Nov 16
MDW6:05 pmChicago Midway
17h 30m
2 stops
GCM12:35 pmGeorge Town Owen Roberts Intl

Air Canada flights from Cayman Islands to Illinois

Our best Air Canada deals on Cayman Islands to Illinois flight tickets
Air Canada
Oct 16
GCM12:50 pmGeorge Town Owen Roberts Intl
45h 01m
2 stops
ORD9:51 amChicago O'Hare Intl
Oct 18
ORD6:00 pmChicago O'Hare Intl
41h 55m
2 stops
GCM11:55 amGeorge Town Owen Roberts Intl
Air Canada
Oct 16
GCM12:50 pmGeorge Town Owen Roberts Intl
21h 01m
2 stops
ORD9:51 amChicago O'Hare Intl
Oct 19
ORD3:35 pmChicago O'Hare Intl
20h 20m
2 stops
GCM11:55 amGeorge Town Owen Roberts Intl
Air Canada
Oct 16
GCM12:50 pmGeorge Town Owen Roberts Intl
28h 43m
1 stop
ORD5:33 pmChicago O'Hare Intl
Oct 18
ORD6:06 pmChicago O'Hare Intl
41h 49m
2 stops
GCM11:55 amGeorge Town Owen Roberts Intl

momondo Fare Finder

 
Customize your flight search to find flights from Cayman Islands to Illinois 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 31, 2025.
Use the filters below to find and compare flights from the Cayman Islands to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 11/14

1:30 pm-9:50 pm

1 stop9h 20m

Chicago O'Hare Intl

Sun 11/16

6:05 am-12:35 pm

1 stop5h 30m

$410

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 10/16

12:50 pm-9:51 am

2 stops45h 01m

Chicago O'Hare Intl

Sat 10/18

6:00 pm-11:55 am

2 stops41h 55m

$447

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 10/16

12:50 pm-9:51 am

2 stops21h 01m

Chicago O'Hare Intl

Sun 10/19

3:35 pm-11:55 am

2 stops20h 20m

$450

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 10/16

12:50 pm-5:33 pm

1 stop28h 43m

Chicago O'Hare Intl

Sat 10/18

6:06 pm-11:55 am

2 stops41h 49m

$466

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 9/12

12:52 pm-9:36 pm

1 stop8h 44m

Chicago Midway

Fri 9/19

6:00 am-11:36 am

1 stop5h 36m

$468

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 9/12

12:52 pm-11:54 pm

1 stop11h 02m

Chicago O'Hare Intl

Fri 9/19

5:30 am-11:36 am

1 stop6h 06m

$468

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 9/12

12:25 pm-11:48 pm

2 stops11h 23m

Chicago O'Hare Intl

Fri 9/19

8:30 pm-11:10 am

2 stops14h 40m

$481

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 8/18

4:45 pm-9:22 am

1 stop16h 37m

Chicago O'Hare Intl

Fri 8/22

10:27 am-9:20 pm

1 stop10h 53m

$482

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 8/18

4:45 pm-9:22 am

1 stop16h 37m

Chicago O'Hare Intl

Wed 8/20

5:21 pm-5:20 pm

1 stop23h 59m

$492

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 9/4

12:10 pm-11:49 pm

1 stop11h 39m

Chicago O'Hare Intl

Thu 12/4

11:57 am-7:51 pm

1 stop6h 54m

$511

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 Illinois from

How to get the cheapest flight ticket from Cayman Islands to Illinois

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 Illinois?

The cheapest day to depart from Cayman Islands to Illinois is on a Sunday when prices can be found for as low as $295. Flights from Cayman Islands to Illinois on a Wednesday will generally be more expensive and average around $1,867. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

Our most recent data shows that the best time of day to fly to Illinois is at noon. Flights from Cayman Islands to Illinois during this time can be as low as $618. Flights in the morning are often more expensive with an average ticket price of $666.

What is the cheapest Cayman Islands to Illinois flight route?

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

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

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

You could potentially save up to 8% on your flight if you consider stops on a Cayman Islands to Illinois flight.

Cheap Cayman Islands to Illinois flight deals and tips

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

Best Price Found

$264

Fastest flight time

4h 10m

Direct flights

Mon, Thu, Fri and Sun

Airports in Illinois

2 airports
The best one-way flight to Illinois from Cayman Islands in the past 72 hours is $264. The best round-trip flight deal from Cayman Islands to Illinois found on momondo in the last 72 hours is $410.
The fastest flight from Cayman Islands to Illinois takes 4h 10m
Direct flights go from Cayman Islands to Illinois on Monday, Thursday, Friday and Sunday. Airlines offering direct flights are: United Airlines and American Airlines.
There are 2 airports near Illinois: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

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

    Prices for flights from Cayman Islands to Illinois were last updated today.

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Cayman Islands to Illinois.

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

    The required travel and health documents for your Illinois 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 Illinois. 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 Cayman Islands to Illinois?


Why use momondo?

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

Finding the right flight to Illinois 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 Illinois quick and easy, saving you time and money.

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

Yes. momondo allows you to filter the results for Cayman Islands to Illinois flights to just show those with flexible booking policies.

How can momondo help me find flights from Cayman Islands to Illinois?

momondo helps you find the best flight between Cayman Islands and Illinois 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 Cayman Islands to Illinois right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Cayman Islands to Illinois flights. All you need is a valid email address and we will do the rest; it is that quick and easy.


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Tue 8/5
Tue 8/12

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