What is the cheapest airline that flies from Cayman Islands to Illinois?

Southwest and Delta are the most popular carriers operating from Cayman Islands to Illinois

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.

$236 Cheap Flights from the Cayman Islands to Illinois in 2026

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Find the cheapest flights from the Cayman Islands to Illinois

Round-trip

One-way

Direct

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

Enter your travel dates to find the best prices.

12:25 pm - 9:00 am

GCM

ORD

20h 35m

1 stop

8:25 pm - 11:25 am

ORD

GCM

15h 00m

1 stop

$403Air Canada

Thu, Jun 11 - Wed, Jun 17

12:25 pm - 9:00 am

GCM

ORD

20h 35m

1 stop

6:22 pm - 11:25 am

ORD

GCM

17h 03m

2 stops

$413Air Canada

Thu, Jun 11 - Wed, Jun 17

12:25 pm - 9:00 am

GCM

ORD

20h 35m

1 stop

8:40 pm - 11:30 am

ORD

GCM

14h 50m

1 stop

$433Air Canada

Sat, Sep 19 - Sun, Sep 27

12:25 pm - 9:00 am

GCM

ORD

20h 35m

1 stop

3:40 pm - 11:30 am

ORD

GCM

19h 50m

2 stops

$436Air Canada

Sat, Sep 19 - Sun, Sep 27

12:25 pm - 10:17 am

GCM

ORD

21h 52m

2 stops

3:40 pm - 11:30 am

ORD

GCM

19h 50m

2 stops

$450Air Canada

Sat, Sep 19 - Sun, Sep 27

7:00 am - 1:23 pm

GCM

ORD

30h 23m

2 stops

9:50 am - 11:30 am

ORD

GCM

25h 40m

1 stop

$549Multiple Airlines

Wed, Oct 7 - Sun, Oct 11

2:10 pm - 8:45 am

GCM

ORD

18h 35m

1 stop

3:40 pm - 11:25 am

ORD

GCM

43h 45m

2 stops

$587Multiple Airlines

Sat, Jul 4 - Sat, Jul 25

12:50 pm - 9:25 pm

GCM

MDW

8h 35m

1 stop

5:10 am - 11:55 am

MDW

GCM

6h 45m

1 stop

$619Southwest

Thu, Jun 11 - Wed, Jun 17

12:55 pm - 9:46 pm

GCM

MDW

8h 51m

1 stop

6:00 am - 11:40 am

MDW

GCM

5h 40m

1 stop

$637Delta

Sat, Sep 19 - Sun, Sep 27

12:50 pm - 11:00 pm

GCM

MDW

10h 10m

2 stops

5:10 am - 11:55 am

MDW

GCM

6h 45m

1 stop

$661Southwest

Thu, Jun 11 - Wed, Jun 17

Air Canada flights from Cayman Islands to Illinois

Our best Air Canada deals on Cayman Islands to Illinois flight tickets

Air Canada

Jun 11

GCM12:25 pmGeorge Town Owen Roberts Intl

20h 35m

1 stop

ORD9:00 amChicago O'Hare Intl

Jun 17

ORD8:25 pmChicago O'Hare Intl

15h 00m

1 stop

GCM11:25 amGeorge Town Owen Roberts Intl

$403

Air Canada

Jun 11

GCM12:25 pmGeorge Town Owen Roberts Intl

20h 35m

1 stop

ORD9:00 amChicago O'Hare Intl

Jun 17

ORD6:22 pmChicago O'Hare Intl

17h 03m

2 stops

GCM11:25 amGeorge Town Owen Roberts Intl

$413

Air Canada

Sep 19

GCM12:25 pmGeorge Town Owen Roberts Intl

20h 35m

1 stop

ORD9:00 amChicago O'Hare Intl

Sep 27

ORD8:40 pmChicago O'Hare Intl

14h 50m

1 stop

GCM11:30 amGeorge Town Owen Roberts Intl

$433

American Airlines flights from Cayman Islands to Illinois

Our best American Airlines deals on Cayman Islands to Illinois flight tickets

American Airlines

Sep 18

GCM12:35 pmGeorge Town Owen Roberts Intl

6h 42m

1 stop

ORD7:17 pmChicago O'Hare Intl

Sep 19

ORD8:44 pmChicago O'Hare Intl

14h 26m

1 stop

GCM11:10 amGeorge Town Owen Roberts Intl

$611

American Airlines

Sep 18

GCM12:35 pmGeorge Town Owen Roberts Intl

6h 42m

1 stop

ORD7:17 pmChicago O'Hare Intl

Sep 19

ORD9:02 pmChicago O'Hare Intl

13h 48m

2 stops

GCM10:50 amGeorge Town Owen Roberts Intl

$616

American Airlines

Jul 4

GCM12:45 pmGeorge Town Owen Roberts Intl

10h 45m

1 stop

ORD11:30 pmChicago O'Hare Intl

Jul 25

ORD5:59 pmChicago O'Hare Intl

17h 01m

1 stop

GCM11:00 amGeorge Town Owen Roberts Intl

$696

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

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

Wed 6/17

8:25 pm-11:25 am

1 stop15h 00m

$403

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

Wed 6/17

6:22 pm-11:25 am

2 stops17h 03m

$413

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 9/19

12:25 pm-9:00 am

1 stop20h 35m

Chicago O'Hare Intl

Sun 9/27

8:40 pm-11:30 am

1 stop14h 50m

$433

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 9/19

12:25 pm-9:00 am

1 stop20h 35m

Chicago O'Hare Intl

Sun 9/27

3:40 pm-11:30 am

2 stops19h 50m

$436

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 9/19

12:25 pm-10:17 am

2 stops21h 52m

Chicago O'Hare Intl

Sun 9/27

3:40 pm-11:30 am

2 stops19h 50m

$450

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 10/7

7:00 am-1:23 pm

2 stops30h 23m

Chicago O'Hare Intl

Sun 10/11

9:50 am-11:30 am

1 stop25h 40m

$549

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 7/4

2:10 pm-8:45 am

1 stop18h 35m

Chicago O'Hare Intl

Sat 7/25

3:40 pm-11:25 am

2 stops43h 45m

$587

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 6/11

12:50 pm-9:25 pm

1 stop8h 35m

Chicago Midway

Wed 6/17

5:10 am-11:55 am

1 stop6h 45m

$619

Quickest round-trip

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 9/19

12:55 pm-9:46 pm

1 stop8h 51m

Chicago Midway

Sun 9/27

6:00 am-11:40 am

1 stop5h 40m

$637

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 6/11

12:50 pm-11:00 pm

2 stops10h 10m

Chicago Midway

Wed 6/17

5:10 am-11:55 am

1 stop6h 45m

$661

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

What is the cheapest month to fly to Illinois?

The cheapest month to fly to Illinois from Cayman Islands is in October. Flight prices, which tend to average around $354, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of October, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $372.

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 $381. Flights from Cayman Islands to Illinois on a Friday will generally be more expensive and average around $2,559. 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 $597. Flights in the afternoon are often more expensive with an average ticket price of $707.

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

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	$402
Fastest flight time	4h 23m
Direct flights	Sun
Airports in Illinois	98 airports

The best one-way flight to Illinois from Cayman Islands in the past 72 hours is $402. The best round-trip flight deal from Cayman Islands to Illinois found on momondo in the last 72 hours is $384.

The fastest flight from Cayman Islands to Illinois takes 4h 23m

Direct flights go from Cayman Islands to Illinois on Sunday. There are no airlines offering direct flights.

There are 98 airports in Illinois. 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 Illinois

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?
Based on momondo bookings for flights between Cayman Islands and Illinois, the leading plane model is Boeing 737-800, making up 42.42% of the total bookings. Other popular models include Boeing 737 MAX 8 with 33.33%, Boeing 737-800 Passenger/BBJ2 (winglets) with 9.09%, and Airbus A320-100/200 with 6.06%.

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.