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Cheap flights from the Cayman Islands to Illinois from $176

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 1/22. 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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0 bags

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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
7:00 am - 6:16 pm
GCM
-
ORD
12h 16m1 stop
Multiple Airlines Logo
9:18 am - 2:50 pm
ORD
-
GCM
28h 32m2 stops
$460Multiple Airlines
Fri, Feb 6 - Fri, Feb 13
United Airlines Logo
2:50 pm - 6:04 pm
GCM
-
ORD
4h 14mnonstop
United Airlines Logo
9:15 pm - 4:20 pm
ORD
-
GCM
18h 05m1 stop
$473United Airlines
Fri, Feb 6 - Fri, Feb 13
American Airlines Logo
3:30 pm - 6:54 pm
GCM
-
ORD
4h 24mnonstop
American Airlines Logo
9:30 am - 2:33 pm
ORD
-
GCM
4h 03mnonstop
$572American Airlines
Fri, Feb 6 - Fri, Feb 13
Multiple Airlines Logo
3:40 pm - 5:44 pm
GCM
-
ORD
27h 04m2 stops
Multiple Airlines Logo
5:10 pm - 4:50 pm
ORD
-
GCM
22h 40m2 stops
$4,823Multiple Airlines
Fri, Feb 6 - Fri, Feb 13

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 December 26, 2025.
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

Fri 2/6

7:00 am-6:16 pm

1 stop12h 16m

Chicago O'Hare Intl

Fri 2/13

9:18 am-2:50 pm

2 stops28h 32m

$460

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 2/6

2:50 pm-6:04 pm

Nonstop4h 14m

Chicago O'Hare Intl

Fri 2/13

9:15 pm-4:20 pm

1 stop18h 05m

$473

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 2/6

3:30 pm-6:54 pm

Nonstop4h 24m

Chicago O'Hare Intl

Fri 2/13

9:30 am-2:33 pm

Nonstop4h 03m

$572

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 2/6

3:40 pm-5:44 pm

2 stops27h 04m

Chicago O'Hare Intl

Fri 2/13

5:10 pm-4:50 pm

2 stops22h 40m

$4,823

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 1/22

2:49 pm-11:46 pm

1 stop9h 57m

$176

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 1/22

2:49 pm-10:36 pm

1 stop8h 47m

$194

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 1/24

2:34 pm-9:03 pm

1 stop7h 29m

$202

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sun 2/22

2:49 pm-11:47 pm

1 stop9h 58m

$221

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 1/20

1:30 pm-10:05 pm

1 stop9h 35m

$225

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 1/19

1:30 pm-5:48 pm

1 stop29h 18m

$230

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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 Wednesday will generally be more expensive and average around $1,867. 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 morning are often more expensive with an average ticket price of $666.

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?

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

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

$258

Fastest flight time

4h 14m

Direct flights

Mon, Tue, 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 $258. The best round-trip flight deal from Cayman Islands to Illinois found on momondo in the last 72 hours is $497.
The fastest flight from Cayman Islands to Illinois takes 4h 14m
Direct flights go from Cayman Islands to Illinois on Monday, Tuesday, 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

  • 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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