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

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

How many flights depart from Cayman Islands to Illinois on average per day?

As of March 2026, there are 1 flights per day flying from Cayman Islands to Illinois. The most common time of day flights depart is 2:00PM, with 100% of flights taking off in the afternoon.

How many flights depart from Cayman Islands to Illinois on average per week?

As of March 2026, 12 flights take off from Cayman Islands and land in Illinois each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

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.

$227 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.

11:10 am - 7:58 am

GCM

ORD

20h 48m

2 stops

5:57 pm - 10:15 am

ORD

GCM

16h 18m

1 stop

$383Air Canada

Fri, Apr 17 - Sun, Apr 26

1:05 pm - 12:15 am

GCM

MDW

11h 10m

1 stop

6:00 am - 12:10 pm

MDW

GCM

6h 10m

1 stop

$420Southwest

Thu, May 14 - Tue, May 19

1:05 pm - 9:55 pm

GCM

ORD

8h 50m

1 stop

5:55 am - 12:10 pm

ORD

GCM

6h 15m

1 stop

$420Southwest

Thu, May 14 - Tue, May 19

11:10 am - 7:58 am

GCM

ORD

20h 48m

2 stops

3:45 pm - 10:15 am

ORD

GCM

18h 30m

2 stops

$436Air Canada

Fri, Apr 17 - Sun, Apr 26

1:05 pm - 12:15 am

GCM

MDW

11h 10m

1 stop

8:55 pm - 12:10 pm

MDW

GCM

15h 15m

2 stops

$455Southwest

Thu, May 14 - Tue, May 19

1:05 pm - 9:55 pm

GCM

ORD

8h 50m

1 stop

7:15 pm - 12:10 pm

ORD

GCM

16h 55m

2 stops

$455Southwest

Thu, May 14 - Tue, May 19

1:05 pm - 11:55 pm

GCM

MDW

10h 50m

2 stops

5:35 am - 12:10 pm

MDW

GCM

6h 35m

1 stop

$476Southwest

Thu, Apr 30 - Mon, May 4

1:05 pm - 8:40 pm

GCM

MDW

7h 35m

1 stop

5:35 am - 12:10 pm

MDW

GCM

6h 35m

1 stop

$492Southwest

Thu, Apr 30 - Mon, May 4

11:25 am - 3:15 pm

GCM

ORD

27h 50m

1 stop

9:50 am - 11:10 am

ORD

GCM

25h 20m

1 stop

$499Air Canada

Mon, Apr 27 - Wed, Apr 29

4:45 pm - 11:59 pm

GCM

ORD

7h 14m

1 stop

8:58 pm - 4:05 pm

ORD

GCM

43h 07m

2 stops

$506Multiple Airlines

Thu, Apr 30 - Mon, May 4

American Airlines flights from Cayman Islands to Illinois

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

American Airlines

May 1

GCM2:10 pmGeorge Town Owen Roberts Intl

9h 44m

2 stops

ORD11:54 pmChicago O'Hare Intl

May 4

ORD8:46 pmChicago O'Hare Intl

14h 14m

2 stops

GCM11:00 amGeorge Town Owen Roberts Intl

$600

American Airlines

Apr 27

GCM2:10 pmGeorge Town Owen Roberts Intl

7h 28m

1 stop

ORD9:38 pmChicago O'Hare Intl

Apr 29

ORD5:00 amChicago O'Hare Intl

8h 10m

2 stops

GCM1:10 pmGeorge Town Owen Roberts Intl

$630

American Airlines

May 10

GCM2:10 pmGeorge Town Owen Roberts Intl

8h 47m

1 stop

ORD10:57 pmChicago O'Hare Intl

May 17

ORD5:00 amChicago O'Hare Intl

6h 31m

1 stop

GCM11:31 amGeorge Town Owen Roberts Intl

$637

Air Canada flights from Cayman Islands to Illinois

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

Air Canada

Apr 17

GCM11:10 amGeorge Town Owen Roberts Intl

20h 48m

2 stops

ORD7:58 amChicago O'Hare Intl

Apr 26

ORD5:57 pmChicago O'Hare Intl

16h 18m

1 stop

GCM10:15 amGeorge Town Owen Roberts Intl

$383

Air Canada

Apr 17

GCM11:10 amGeorge Town Owen Roberts Intl

20h 48m

2 stops

ORD7:58 amChicago O'Hare Intl

Apr 26

ORD3:45 pmChicago O'Hare Intl

18h 30m

2 stops

GCM10:15 amGeorge Town Owen Roberts Intl

$436

Air Canada

Apr 27

GCM11:25 amGeorge Town Owen Roberts Intl

27h 50m

1 stop

ORD3:15 pmChicago O'Hare Intl

Apr 29

ORD7:55 amChicago O'Hare Intl

27h 15m

1 stop

GCM11:10 amGeorge Town Owen Roberts Intl

$515

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 4/17

11:10 am-7:58 am

2 stops20h 48m

Chicago O'Hare Intl

Sun 4/26

5:57 pm-10:15 am

1 stop16h 18m

$383

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 5/14

1:05 pm-12:15 am

1 stop11h 10m

Chicago Midway

Tue 5/19

6:00 am-12:10 pm

1 stop6h 10m

$420

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 5/14

1:05 pm-9:55 pm

1 stop8h 50m

Chicago O'Hare Intl

Tue 5/19

5:55 am-12:10 pm

1 stop6h 15m

$420

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 4/17

11:10 am-7:58 am

2 stops20h 48m

Chicago O'Hare Intl

Sun 4/26

3:45 pm-10:15 am

2 stops18h 30m

$436

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 5/14

1:05 pm-12:15 am

1 stop11h 10m

Chicago Midway

Tue 5/19

8:55 pm-12:10 pm

2 stops15h 15m

$455

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 5/14

1:05 pm-9:55 pm

1 stop8h 50m

Chicago O'Hare Intl

Tue 5/19

7:15 pm-12:10 pm

2 stops16h 55m

$455

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 4/30

1:05 pm-11:55 pm

2 stops10h 50m

Chicago Midway

Mon 5/4

5:35 am-12:10 pm

1 stop6h 35m

$476

Quickest round-trip

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 4/30

1:05 pm-8:40 pm

1 stop7h 35m

Chicago Midway

Mon 5/4

5:35 am-12:10 pm

1 stop6h 35m

$492

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 4/27

11:25 am-3:15 pm

1 stop27h 50m

Chicago O'Hare Intl

Wed 4/29

9:50 am-11:10 am

1 stop25h 20m

$499

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 4/30

4:45 pm-11:59 pm

1 stop7h 14m

Chicago O'Hare Intl

Mon 5/4

8:58 pm-4:05 pm

2 stops43h 07m

$506

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

Other information

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 Wednesday will generally be more expensive and average around $2,042. 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 $513. 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

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 55% 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	$389
Fastest flight time	4h 23m
Direct flights	Tue, Wed, Sat and Sun
Airports in Illinois	98 airports

The best one-way flight to Illinois from Cayman Islands in the past 72 hours is $389. The best round-trip flight deal from Cayman Islands to Illinois found on momondo in the last 72 hours is $513.

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

Direct flights go from Cayman Islands to Illinois on Tuesday, Wednesday, Saturday and 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

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 51.72% of the total bookings. Other popular models include Boeing 737 MAX 8 with 20.69%, Boeing 737-800 Passenger/BBJ2 (winglets) with 10.34%, and Airbus A320-100/200 with 6.90%.

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.