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

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

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

As of July 2026, 1 flights take off from Cayman Islands and land in Illinois each week. The most common flight departure day for this route is Sat, with 100% 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 many operators does momondo search for flights from Cayman Islands to Illinois?

There is 1 operator available for flights from Cayman Islands to Illinois as of July 2026.

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.

$289 Cheap Flights from the Cayman Islands to Illinois in 2026

Discover deals from 900+ travel sites with momondo.

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

8:40 pm - 11:30 am

ORD

GCM

14h 50m

1 stop

$478Air Canada

Thu, Oct 8 - Wed, Oct 14

12:25 pm - 9:00 am

GCM

ORD

20h 35m

1 stop

3:40 pm - 11:30 am

ORD

GCM

19h 50m

2 stops

$482Air Canada

Thu, Oct 8 - Wed, Oct 14

12:35 pm - 11:00 pm

GCM

ORD

10h 25m

1 stop

5:18 am - 11:30 am

ORD

GCM

6h 12m

1 stop

$591American Airlines

Thu, Oct 8 - Tue, Oct 13

12:00 pm - 11:00 pm

GCM

ORD

11h 00m

2 stops

5:18 am - 11:30 am

ORD

GCM

6h 12m

1 stop

$596American Airlines

Thu, Oct 8 - Tue, Oct 13

1:04 pm - 10:36 pm

GCM

MDW

9h 32m

1 stop

6:05 am - 11:39 am

MDW

GCM

5h 34m

1 stop

$672Delta

Tue, Aug 4 - Tue, Aug 11

12:56 pm - 10:15 pm

GCM

MDW

9h 19m

1 stop

6:42 pm - 11:39 am

MDW

GCM

16h 57m

2 stops

$759Delta

Sat, Aug 1 - Sat, Aug 8

1:30 pm - 10:40 pm

GCM

MDW

10h 10m

2 stops

7:30 pm - 12:55 pm

MDW

GCM

16h 25m

2 stops

$779Southwest

Thu, Dec 31 - Wed, Jan 6

1:30 pm - 10:40 pm

GCM

MDW

10h 10m

2 stops

5:45 am - 12:55 pm

MDW

GCM

6h 10m

1 stop

$811Southwest

Thu, Dec 31 - Wed, Jan 6

11:30 am - 6:33 pm

GCM

MDW

31h 03m

3 stops

9:24 am - 9:00 pm

MDW

GCM

35h 36m

3 stops

$1,264Multiple Airlines

Tue, Aug 11 - Tue, Aug 18

10:40 am - 6:25 pm

GCM

MDW

31h 45m

2 stops

9:59 am - 9:15 pm

MDW

GCM

35h 16m

3 stops

$1,568Multiple Airlines

Sat, Aug 1 - Sat, Aug 8

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American Airlines flights from Cayman Islands to Illinois

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

American Airlines

Oct 8

GCM12:35 pmGeorge Town Owen Roberts Intl

10h 25m

1 stop

ORD11:00 pmChicago O'Hare Intl

Oct 13

ORD5:18 amChicago O'Hare Intl

6h 12m

1 stop

GCM11:30 amGeorge Town Owen Roberts Intl

$591

American Airlines

Oct 8

GCM12:00 pmGeorge Town Owen Roberts Intl

11h 00m

2 stops

ORD11:00 pmChicago O'Hare Intl

Oct 13

ORD5:18 amChicago O'Hare Intl

6h 12m

1 stop

GCM11:30 amGeorge Town Owen Roberts Intl

$596

American Airlines

Oct 8

GCM12:35 pmGeorge Town Owen Roberts Intl

10h 25m

1 stop

ORD11:00 pmChicago O'Hare Intl

Oct 13

ORD5:18 amChicago O'Hare Intl

6h 12m

1 stop

GCM11:30 amGeorge Town Owen Roberts Intl

$611

United Airlines flights from Cayman Islands to Illinois

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

United Airlines

Aug 1

GCM1:50 pmGeorge Town Owen Roberts Intl

4h 23m

ORD6:13 pmChicago O'Hare Intl

Aug 8

ORD7:35 amChicago O'Hare Intl

8h 00m

1 stop

GCM3:35 pmGeorge Town Owen Roberts Intl

$834

United Airlines

Aug 15

GCM2:45 pmGeorge Town Owen Roberts Intl

8h 37m

1 stop

ORD11:22 pmChicago O'Hare Intl

Dec 18

ORD8:45 amChicago O'Hare Intl

4h 00m

GCM1:45 pmGeorge Town Owen Roberts Intl

$870

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

8:40 pm-11:30 am

1 stop14h 50m

$478

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

3:40 pm-11:30 am

2 stops19h 50m

$482

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 10/8

12:35 pm-11:00 pm

1 stop10h 25m

Chicago O'Hare Intl

Tue 10/13

5:18 am-11:30 am

1 stop6h 12m

$591

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 10/8

12:00 pm-11:00 pm

2 stops11h 00m

Chicago O'Hare Intl

Tue 10/13

5:18 am-11:30 am

1 stop6h 12m

$596

Quickest round-trip

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Tue 8/4

1:04 pm-10:36 pm

1 stop9h 32m

Chicago Midway

Tue 8/11

6:05 am-11:39 am

1 stop5h 34m

$672

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 8/1

12:56 pm-10:15 pm

1 stop9h 19m

Chicago Midway

Sat 8/8

6:42 pm-11:39 am

2 stops16h 57m

$759

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 12/31

1:30 pm-10:40 pm

2 stops10h 10m

Chicago Midway

Wed 1/6

7:30 pm-12:55 pm

2 stops16h 25m

$779

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 12/31

1:30 pm-10:40 pm

2 stops10h 10m

Chicago Midway

Wed 1/6

5:45 am-12:55 pm

1 stop6h 10m

$811

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Tue 8/11

11:30 am-6:33 pm

3 stops31h 03m

Chicago Midway

Tue 8/18

9:24 am-9:00 pm

3 stops35h 36m

$1,264

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 8/1

10:40 am-6:25 pm

2 stops31h 45m

Chicago Midway

Sat 8/8

9:59 am-9:15 pm

3 stops35h 16m

$1,568

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 month to fly to Illinois?

The cheapest month to fly to Illinois from Cayman Islands is in September. Flight prices, which tend to average around $0, 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 September, 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 Saturday when prices can be found for as low as $470. 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 $571. 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 3 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 17% 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	$333
Fastest flight time	4h 14m
Direct flights	Wed, Thu, Fri, Sat and Sun
Airports in Illinois	98 airports

The best one-way flight to Illinois from Cayman Islands in the past 72 hours is $333. The best round-trip flight deal from Cayman Islands to Illinois found on momondo in the last 72 hours is $636.

The fastest flight from Cayman Islands to Illinois takes 4h 14m

Direct flights go from Cayman Islands to Illinois on Wednesday, Thursday, Friday, 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

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 many operators does momondo search for flights from Cayman Islands to Illinois?
There is 1 operator available for flights from Cayman Islands to Illinois as of July 2026.
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 MAX 8, making up 36.67% of the total bookings. Other popular models include Boeing 737-800 with 36.67%, Boeing 737-800 Passenger/BBJ2 (winglets) with 10.00%, and Airbus A320-100/200 with 6.67%.

Best airlines flying from Cayman Islands to Illinois

Compare and see reviews for airlines that fly from Cayman Islands to Illinois with momondo

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $389	Free Cancellation	Rating 7.1 11,782 reviews		Search American Airlines flights

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.