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Cayman Islands

$58+ Cheap flights from Illinois to the Cayman Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Illinois to Cayman Islands

Cheapest flights from Illinois to Cayman Islands
Explore the most affordable flight options available from Illinois to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Orbitz deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:16 pm
ORD
-
GCM
1 stop16h 27m
Multiple Airlines
Mon 3/23:40 pm
GCM
-
ORD
1 stop21h 09m
Multiple Airlines
Deal found 1/27$346
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2112:06 pm
ORD
-
GCM
1 stop24h 37m
Multiple Airlines
Wed 2/2511:30 am
GCM
-
ORD
1 stop23h 09m
Multiple Airlines
Deal found 1/27$355
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:15 am
ORD
-
GCM
1 stop7h 28m
Multiple Airlines
Mon 3/24:45 pm
GCM
-
ORD
2 stops25h 07m
Multiple Airlines
Deal found 1/28$356
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/48:16 pm
ORD
-
GCM
1 stop16h 27m
Multiple Airlines
Sat 3/78:50 am
GCM
-
ORD
2 stops16h 31m
Multiple Airlines
Deal found 1/28$358
This Delta deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/25:55 am
MLI
-
GCM
1 stop5h 34m
Delta
Tue 3/101:12 pm
GCM
-
MLI
1 stop9h 18m
Delta
Deal found 1/28$359
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/39:23 am
ORD
-
GCM
1 stop29h 42m
Multiple Airlines
Thu 2/52:49 pm
GCM
-
ORD
1 stop7h 14m
Multiple Airlines
Deal found 1/27$361
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/85:15 am
ORD
-
GCM
1 stop7h 38m
Spirit Airlines
Thu 2/122:49 pm
GCM
-
ORD
2 stops18h 05m
Spirit Airlines
Deal found 1/27$363
This Mytrip deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/118:42 pm
ORD
-
GCM
2 stops16h 15m
Multiple Airlines
Wed 3/1811:30 am
GCM
-
ORD
1 stop7h 05m
Multiple Airlines
Deal found 1/27$365
This Mytrip deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/118:55 pm
ORD
-
GCM
2 stops16h 02m
Multiple Airlines
Wed 4/1511:30 am
GCM
-
ORD
1 stop6h 45m
Multiple Airlines
Deal found 1/27$366
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/45:32 pm
ORD
-
GCM
1 stop19h 21m
Multiple Airlines
Fri 2/64:45 pm
GCM
-
ORD
1 stop16h 33m
Multiple Airlines
Deal found 1/28$367
This Kiwi.com deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/258:16 pm
ORD
-
GCM
1 stop16h 27m
Multiple Airlines
Wed 3/411:30 am
GCM
-
ORD
2 stops21h 24m
Multiple Airlines
Deal found 1/26$368
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:15 am
ORD
-
GCM
1 stop7h 28m
Spirit Airlines
Thu 3/52:49 pm
GCM
-
ORD
2 stops10h 51m
Spirit Airlines
Deal found 1/27$369

Find flight deals from Illinois to Cayman Islands

Keep the following information in mind while searching for Illinois to Cayman Islands flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$346
(Orbitz)

One-way from

$58
(Expedia)

Popular in

December

Cheapest in

October

Average price

$560

Good round-trip deal

$498 or less

Good one-way deal

$288 or less
Provider with most accurate pricing for Chicago (CHI)-George Town Owen Roberts Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-George Town Owen Roberts Intl flights.
Search Deals
From Illinois to Cayman Islands
Search Deals
One-way flight from Illinois to Cayman Islands
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Illinois to Cayman Islands.
Search Deals
Price to beat on a one-way flight from Illinois to Cayman Islands.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Cayman Islands 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, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
Use the filters below to find and compare flights from Illinois to the Cayman Islands that are best for you.

Fly from

Illinois

Fly to

Cayman Islands

Route

Depart

Return

Price

MolineGeorge Town

MLI - GCM

MLIGCM

Moline Quad-City

Mon 3/2

5:55 am-12:29 pm

1 stop5h 34m

George Town Owen Roberts Intl

Tue 3/10

1:12 pm-10:30 pm

1 stop9h 18m

$359

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 3/14

8:55 pm-12:57 pm

2 stops16h 02m

George Town Owen Roberts Intl

Thu 3/19

1:52 pm-11:17 pm

1 stop9h 25m

$377

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Sat 2/14

6:00 am-2:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Sat 2/21

3:56 pm-11:23 pm

1 stop8h 27m

$405

MolineGeorge Town

MLI - GCM

MLIGCM

Moline Quad-City

Mon 3/2

7:00 am-8:15 pm

2 stops12h 15m

George Town Owen Roberts Intl

Tue 3/10

7:45 am-8:59 pm

2 stops13h 14m

$415

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 4/11

8:55 pm-12:57 pm

2 stops16h 02m

George Town Owen Roberts Intl

Wed 4/15

11:30 am-9:12 am

2 stops21h 42m

$422

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Sat 6/6

1:00 pm-11:30 am

2 stops46h 30m

George Town Owen Roberts Intl

Thu 6/11

12:25 pm-12:06 pm

1 stop23h 41m

$429

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 2/26

8:40 pm-12:25 pm

1 stop14h 45m

George Town Owen Roberts Intl

Tue 3/3

1:30 pm-12:48 pm

2 stops24h 18m

$432

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Sat 4/18

6:53 pm-11:32 am

1 stop16h 39m

George Town Owen Roberts Intl

Sat 5/2

3:13 pm-11:04 pm

1 stop7h 51m

$438

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 3/19

6:16 pm-6:00 pm

1 stop23h 44m

George Town Owen Roberts Intl

Mon 3/23

4:45 pm-8:25 am

1 stop15h 40m

$439

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Tue 3/31

6:00 am-12:30 pm

1 stop6h 30m

George Town Owen Roberts Intl

Wed 4/1

1:35 pm-10:28 pm

1 stop8h 53m

$477

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 50 results
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Best time to book a flight from Illinois to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Illinois with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Illinois to the Cayman Islands

What is the cheapest month to book a flight from Illinois to Cayman Islands?

Currently, December is the cheapest month in which you can book a flight from Illinois to Cayman Islands (average of $322). Flying from Illinois to Cayman Islands in September is currently the most expensive (average of $650). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from IL to KY?

Find hourly flight availability from Illinois to Cayman Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 29, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Cayman Islands as you normally would.

Related info for your journey

Find useful and relevant information for your journey from Illinois to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Illinois to Cayman Islands?

    Airlines like Delta, Spirit Airlines, and American Airlines fly from Illinois to Cayman Islands in about 5h 34m. The time it takes to get you to your destination can typically vary by up to 10h 28m. Airlines will cover a distance of 1622 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Illinois to Cayman Islands one-way?

    To fly one-way, consider booking your trip with Air Canada, which is currently one of the cheapest options available, starting at $137. American Airlines flights start at $250 while deals on United Airlines start at $288 one-way.

  • Can I find deals for flights from Illinois to Cayman Islands that include hotel bookings?

    Yes. In addition to deals on Illinois to Cayman Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Cayman Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Cayman Islands.

  • Can I find deals for business class flights from Illinois to Cayman Islands?

    Yes. Cheapflights offers flight deals from Illinois to Cayman Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Illinois to Cayman Islands?

    Currently, December is the cheapest month in which you can book a flight from Illinois to Cayman Islands (average of $322). Flying from Illinois to Cayman Islands in September is currently the most expensive (average of $650). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Illinois to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Illinois to Cayman Islands

Discover the top 2 airlines that operate flights from Illinois to Cayman Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$341Average$624FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$438Average$707FlexibilityNo cancel feeOn-time71%

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