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Cheap flights from the Cayman Islands to Illinois from $193

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 5/7. 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 Illinois

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

Enter your travel dates to find the best prices.
Multiple Airlines Logo
4:45 pm - 9:39 am
GCM
-
ORD
16h 54m
1 stop
Multiple Airlines Logo
6:36 pm - 12:57 pm
ORD
-
GCM
18h 21m
1 stop
$331Multiple Airlines
Mon, Mar 9 - Wed, Mar 11
Multiple Airlines Logo
7:00 am - 9:39 am
GCM
-
ORD
26h 39m
1 stop
Multiple Airlines Logo
5:05 am - 12:57 pm
ORD
-
GCM
7h 52m
1 stop
$354Multiple Airlines
Mon, Mar 9 - Thu, Mar 12
Multiple Airlines Logo
4:45 pm - 9:39 am
GCM
-
ORD
16h 54m
1 stop
Multiple Airlines Logo
12:44 pm - 12:57 pm
ORD
-
GCM
24h 13m
2 stops
$365Multiple Airlines
Mon, Mar 9 - Wed, Mar 11
Multiple Airlines Logo
1:40 pm - 11:41 pm
GCM
-
ORD
10h 01m
1 stop
Multiple Airlines Logo
3:50 pm - 11:30 am
ORD
-
GCM
19h 40m
1 stop
$371Multiple Airlines
Thu, May 28 - Sun, May 31
Spirit Airlines Logo
1:52 pm - 11:17 pm
GCM
-
ORD
9h 25m
1 stop
Spirit Airlines Logo
5:05 am - 12:57 pm
ORD
-
GCM
7h 52m
1 stop
$382Spirit Airlines
Thu, Mar 26 - Thu, Apr 2
Multiple Airlines Logo
7:00 am - 8:23 am
GCM
-
ORD
25h 23m
2 stops
Multiple Airlines Logo
5:05 am - 12:57 pm
ORD
-
GCM
7h 52m
1 stop
$391Multiple Airlines
Mon, Mar 9 - Thu, Mar 12
Multiple Airlines Logo
11:25 am - 1:05 pm
GCM
-
ORD
25h 40m
1 stop
Multiple Airlines Logo
6:01 pm - 12:20 pm
ORD
-
GCM
18h 19m
2 stops
$393Multiple Airlines
Mon, Apr 6 - Fri, Apr 10
Southwest Logo
12:40 pm - 8:15 pm
GCM
-
MDW
7h 35m
1 stop
Southwest Logo
6:00 am - 11:25 am
MDW
-
GCM
5h 25m
1 stop
$883Southwest
Thu, Mar 26 - Thu, Apr 2
Southwest Logo
12:40 pm - 11:00 pm
GCM
-
MDW
10h 20m
2 stops
Southwest Logo
8:15 pm - 11:40 am
MDW
-
GCM
15h 25m
2 stops
$912Southwest
Thu, Mar 26 - Thu, Apr 2
Delta Logo
1:12 pm - 10:31 pm
GCM
-
MDW
9h 19m
1 stop
Delta Logo
6:00 am - 11:47 am
MDW
-
GCM
5h 47m
1 stop
$1,419Delta
Thu, Apr 2 - Tue, Apr 7

American Airlines flights from Cayman Islands to Illinois

Our best American Airlines deals on Cayman Islands to Illinois flight tickets
American Airlines
Mar 9
GCM2:44 pmGeorge Town Owen Roberts Intl
4h 10m
ORD6:54 pmChicago O'Hare Intl
Mar 11
ORD9:45 amChicago O'Hare Intl
3h 59m
GCM1:44 pmGeorge Town Owen Roberts Intl
$533
American Airlines
Mar 9
GCM2:44 pmGeorge Town Owen Roberts Intl
4h 10m
ORD6:54 pmChicago O'Hare Intl
Mar 11
ORD5:00 amChicago O'Hare Intl
6h 10m
1 stop
GCM11:10 amGeorge Town Owen Roberts Intl
$537
American Airlines
Feb 12
GCM3:35 pmGeorge Town Owen Roberts Intl
4h 10m
ORD6:45 pmChicago O'Hare Intl
Feb 23
ORD6:10 amChicago O'Hare Intl
8h 15m
1 stop
GCM3:25 pmGeorge Town Owen Roberts Intl
$557

United Airlines flights from Cayman Islands to Illinois

Our best United Airlines deals on Cayman Islands to Illinois flight tickets
United Airlines
Mar 26
GCM4:45 pmGeorge Town Owen Roberts Intl
15h 01m
1 stop
ORD7:46 amChicago O'Hare Intl
Apr 2
ORD8:45 amChicago O'Hare Intl
4h 00m
GCM12:45 pmGeorge Town Owen Roberts Intl
$526
United Airlines
Mar 27
GCM4:45 pmGeorge Town Owen Roberts Intl
16h 22m
1 stop
ORD9:07 amChicago O'Hare Intl
Apr 3
ORD8:45 amChicago O'Hare Intl
4h 00m
GCM12:45 pmGeorge Town Owen Roberts Intl
$536
United Airlines
Feb 12
GCM2:50 pmGeorge Town Owen Roberts Intl
4h 14m
ORD6:04 pmChicago O'Hare Intl
Feb 23
ORD8:45 amChicago O'Hare Intl
4h 00m
GCM1:45 pmGeorge Town Owen Roberts Intl
$553

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 February 11, 2026.
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

Mon 3/9

4:45 pm-9:39 am

1 stop16h 54m

Chicago O'Hare Intl

Wed 3/11

6:36 pm-12:57 pm

1 stop18h 21m

$331

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 3/9

7:00 am-9:39 am

1 stop26h 39m

Chicago O'Hare Intl

Thu 3/12

5:05 am-12:57 pm

1 stop7h 52m

$354

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 3/9

4:45 pm-9:39 am

1 stop16h 54m

Chicago O'Hare Intl

Wed 3/11

12:44 pm-12:57 pm

2 stops24h 13m

$365

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 5/28

1:40 pm-11:41 pm

1 stop10h 01m

Chicago O'Hare Intl

Sun 5/31

3:50 pm-11:30 am

1 stop19h 40m

$371

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 3/26

1:52 pm-11:17 pm

1 stop9h 25m

Chicago O'Hare Intl

Thu 4/2

5:05 am-12:57 pm

1 stop7h 52m

$382

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 3/9

7:00 am-8:23 am

2 stops25h 23m

Chicago O'Hare Intl

Thu 3/12

5:05 am-12:57 pm

1 stop7h 52m

$391

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 4/6

11:25 am-1:05 pm

1 stop25h 40m

Chicago O'Hare Intl

Fri 4/10

6:01 pm-12:20 pm

2 stops18h 19m

$393

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 3/26

12:40 pm-8:15 pm

1 stop7h 35m

Chicago Midway

Thu 4/2

6:00 am-11:25 am

1 stop5h 25m

$883

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 3/26

12:40 pm-11:00 pm

2 stops10h 20m

Chicago Midway

Thu 4/2

8:15 pm-11:40 am

2 stops15h 25m

$912

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 4/2

1:12 pm-10:31 pm

1 stop9h 19m

Chicago Midway

Tue 4/7

6:00 am-11:47 am

1 stop5h 47m

$1,419

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 $373. Flights from Cayman Islands to Illinois on a Tuesday will generally be more expensive and average around $1,469. 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 $497. Flights in the afternoon are often more expensive with an average ticket price of $571.

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 53% 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

$220

Fastest flight time

4h 14m

Direct flights

Every day

Airports in Illinois

98 airports
The best one-way flight to Illinois from Cayman Islands in the past 72 hours is $220. The best round-trip flight deal from Cayman Islands to Illinois found on momondo in the last 72 hours is $276.
The fastest flight from Cayman Islands to Illinois takes 4h 14m
Direct flights go from Cayman Islands to Illinois every day.
There are 98 airports in Illinois. 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 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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