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

As of March 2026, 6 flights take off from Grand Cayman and land in Illinois each week. The most common flight departure day for this route is Thu, with 33% of weekly flights taking off on this day.

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

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

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

Prices for flights from Grand Cayman to Illinois are updated daily.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Grand Cayman 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.

$222 Cheap Flights from Grand Cayman to Illinois in 2026

1 adult

0 bags

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Find the cheapest flights from Grand Cayman to Illinois

Round-trip

One-way

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

11:30 am - 6:31 pm

GCM

ORD

7h 01m

1 stop

4:58 pm - 4:05 pm

ORD

GCM

23h 07m

1 stop

$405Multiple Airlines

Tue, Apr 14 - Mon, Apr 20

11:25 am - 8:03 am

GCM

ORD

20h 38m

1 stop

6:40 pm - 11:10 am

ORD

GCM

16h 30m

1 stop

$416Air Canada

Mon, Mar 30 - Mon, Apr 6

11:25 am - 8:03 am

GCM

ORD

20h 38m

1 stop

3:45 pm - 11:10 am

ORD

GCM

19h 25m

2 stops

$420Air Canada

Mon, Mar 30 - Mon, Apr 6

1:05 pm - 12:05 am

GCM

MDW

11h 00m

1 stop

5:35 am - 12:10 pm

MDW

GCM

6h 35m

1 stop

$422Southwest

Thu, Apr 23 - Mon, Apr 27

1:05 pm - 9:55 pm

GCM

ORD

8h 50m

1 stop

6:00 am - 12:10 pm

ORD

GCM

6h 10m

1 stop

$422Southwest

Thu, Apr 23 - Mon, Apr 27

1:05 pm - 11:30 pm

GCM

MDW

10h 25m

2 stops

5:35 am - 12:10 pm

MDW

GCM

6h 35m

1 stop

$427Southwest

Thu, Apr 23 - Mon, Apr 27

12:30 pm - 9:10 am

GCM

ORD

20h 40m

1 stop

6:40 pm - 11:10 am

ORD

GCM

16h 30m

1 stop

$431Air Canada

Tue, Mar 31 - Mon, Apr 6

11:30 am - 6:31 pm

GCM

ORD

7h 01m

1 stop

6:08 pm - 4:05 pm

ORD

GCM

21h 57m

2 stops

$432Multiple Airlines

Tue, Apr 14 - Tue, Apr 21

1:25 pm - 10:28 pm

GCM

MDW

9h 03m

1 stop

6:00 am - 12:00 pm

MDW

GCM

6h 00m

1 stop

$510Delta

Tue, Apr 14 - Tue, Apr 21

1:25 pm - 8:47 am

GCM

MDW

19h 22m

2 stops

1:24 pm - 12:00 pm

MDW

GCM

22h 36m

2 stops

$540Delta

Tue, Apr 14 - Thu, Apr 23

Air Canada flights from Grand Cayman to Illinois

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

Air Canada

Mar 30

GCM11:25 amGeorge Town Owen Roberts Intl

20h 38m

1 stop

ORD8:03 amChicago O'Hare Intl

Apr 6

ORD6:40 pmChicago O'Hare Intl

16h 30m

1 stop

GCM11:10 amGeorge Town Owen Roberts Intl

$416

Air Canada

Mar 30

GCM11:25 amGeorge Town Owen Roberts Intl

20h 38m

1 stop

ORD8:03 amChicago O'Hare Intl

Apr 6

ORD3:45 pmChicago O'Hare Intl

19h 25m

2 stops

GCM11:10 amGeorge Town Owen Roberts Intl

$420

Air Canada

Mar 31

GCM12:30 pmGeorge Town Owen Roberts Intl

20h 40m

1 stop

ORD9:10 amChicago O'Hare Intl

Apr 6

ORD6:40 pmChicago O'Hare Intl

16h 30m

1 stop

GCM11:10 amGeorge Town Owen Roberts Intl

$431

Spirit Airlines flights from Grand Cayman to Illinois

Our best Spirit Airlines deals on Grand Cayman to Illinois flight tickets

Spirit Airlines

Mar 28

GCM1:15 pmGeorge Town Owen Roberts Intl

18h 46m

2 stops

ORD8:01 amChicago O'Hare Intl

Apr 4

ORD5:05 amChicago O'Hare Intl

7h 15m

1 stop

GCM12:20 pmGeorge Town Owen Roberts Intl

$504

Spirit Airlines

Mar 28

GCM1:15 pmGeorge Town Owen Roberts Intl

18h 46m

2 stops

ORD8:01 amChicago O'Hare Intl

Apr 4

ORD12:45 pmChicago O'Hare Intl

24h 12m

3 stops

GCM12:57 pmGeorge Town Owen Roberts Intl

$563

Fly from

Fly to

Route

Depart

Return

Price

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 4/14

11:30 am-6:31 pm

1 stop7h 01m

Chicago O'Hare Intl

Mon 4/20

4:58 pm-4:05 pm

1 stop23h 07m

$405

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 3/30

11:25 am-8:03 am

1 stop20h 38m

Chicago O'Hare Intl

Mon 4/6

6:40 pm-11:10 am

1 stop16h 30m

$416

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 3/30

11:25 am-8:03 am

1 stop20h 38m

Chicago O'Hare Intl

Mon 4/6

3:45 pm-11:10 am

2 stops19h 25m

$420

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 4/23

1:05 pm-12:05 am

1 stop11h 00m

Chicago Midway

Mon 4/27

5:35 am-12:10 pm

1 stop6h 35m

$422

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 4/23

1:05 pm-9:55 pm

1 stop8h 50m

Chicago O'Hare Intl

Mon 4/27

6:00 am-12:10 pm

1 stop6h 10m

$422

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 4/23

1:05 pm-11:30 pm

2 stops10h 25m

Chicago Midway

Mon 4/27

5:35 am-12:10 pm

1 stop6h 35m

$427

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 3/31

12:30 pm-9:10 am

1 stop20h 40m

Chicago O'Hare Intl

Mon 4/6

6:40 pm-11:10 am

1 stop16h 30m

$431

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 4/14

11:30 am-6:31 pm

1 stop7h 01m

Chicago O'Hare Intl

Tue 4/21

6:08 pm-4:05 pm

2 stops21h 57m

$432

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Tue 4/14

1:25 pm-10:28 pm

1 stop9h 03m

Chicago Midway

Tue 4/21

6:00 am-12:00 pm

1 stop6h 00m

$510

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Tue 4/14

1:25 pm-8:47 am

2 stops19h 22m

Chicago Midway

Thu 4/23

1:24 pm-12:00 pm

2 stops22h 36m

$540

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 Grand Cayman 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 Grand Cayman to Illinois is on a Sunday when prices can be found for as low as $373. Flights from Grand Cayman 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 Grand Cayman 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 $707.

What is the cheapest Grand Cayman to Illinois flight route?

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

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

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

No. A direct flight is the cheapest option for a flight between Grand Cayman to Illinois.

Cheap Grand Cayman to Illinois flight deals and tips

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

Fastest flight time	4h 23m
Direct flights	Every day
Airports in Illinois	98 airports

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

Direct flights go from Grand Cayman to Illinois every day.

There are 98 airports in Illinois. From Grand Cayman there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

When did momondo last update prices for flights from Grand Cayman to Illinois?
Prices for flights from Grand Cayman to Illinois are updated daily.
How old do you have to be to fly from Grand Cayman to Illinois?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Grand Cayman 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 Grand Cayman to Illinois?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Grand Cayman to Illinois is Boeing 737-800 (17.95% of total bookings). The next most popular plane models are Airbus A321neo (12.92%), Boeing 737 MAX 8 (8.24%), and Boeing 737-900 (7.38%).

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Grand Cayman to Illinois. momondo saves you time and could save you money on your trip.

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

Yes. momondo enables you to select and highlight flights to Illinois from Grand Cayman with this policy.

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

Once you have performed a search for Grand Cayman to Illinois flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Grand Cayman to Illinois right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Illinois, momondo offers a useful price alert feature which will track prices for flights to Illinois from Grand Cayman and alert you when they change.