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Cayman Islands

$124+ 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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap 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 September 15, 2025.

Round-trip from

$311
(Priceline)

One-way from

$124
(Priceline)

Popular in

December

Cheapest in

October

Average price

$569

Good round-trip deal

$555 or less

Good one-way deal

$582 or less
From Illinois to Cayman Islands
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One-way flight from Illinois to Cayman Islands
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Highest demand for flights based on searches. 8% potential increase in price ($59 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Illinois to Cayman Islands.
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Price to beat on a one-way flight from Illinois to Cayman Islands.
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Find 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 September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/126:05 amORD - GCM
1 stop5h 30mSouthwest
Thu 11/201:30 pmGCM - ORD
1 stop9h 20mSouthwest
Deal found 9/12$426
This Air Canada deal was found by Cheapflights users on 9/12. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/138:15 pmORD - GCM
1 stop15h 10mAir Canada
Fri 11/211:30 pmGCM - ORD
1 stop9h 35mAir Canada
Deal found 9/12$430
This JetBlue deal was found by Cheapflights users on 9/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/146:55 pmORD - GCM
1 stop15h 59mJetBlue
Sun 11/233:36 pmGCM - ORD
1 stop8h 14mJetBlue
Deal found 9/13$431
This Booking.com deal was found by Cheapflights users on 9/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/287:20 amORD - GCM
2 stops52h 05mAir Canada
Thu 11/61:30 pmGCM - ORD
1 stop26h 40mAir Canada
Deal found 9/13$438
This Booking.com deal was found by Cheapflights users on 9/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/26:05 pmORD - GCM
2 stops41h 20mAir Canada
Tue 12/91:30 pmGCM - ORD
2 stops43h 31mAir Canada
Deal found 9/14$439
This American Airlines deal was found by Cheapflights users on 9/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/145:20 amORD - GCM
1 stop6h 00mAmerican Airlines
Tue 10/2112:10 pmGCM - ORD
1 stop9h 13mAmerican Airlines
Deal found 9/14$446
This American Airlines deal was found by Cheapflights users on 9/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2112:51 pmSTL - GCM
1 stop22h 29mAmerican Airlines
Tue 10/2812:25 pmGCM - STL
1 stop10h 40mAmerican Airlines
Deal found 9/14$447
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/276:55 pmORD - GCM
1 stop16h 27mAmerican Airlines
Tue 9/3012:10 pmGCM - ORD
2 stops19h 32mAmerican Airlines
Deal found 9/13$450
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/75:50 amMDW - GCM
1 stop5h 45mSouthwest
Fri 12/121:30 pmGCM - MDW
2 stops11h 00mSouthwest
Deal found 9/14$450
This Delta deal was found by Cheapflights users on 9/13. 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.
Sun 11/167:52 pmORD - GCM
1 stop15h 43mDelta
Fri 11/211:50 pmGCM - ORD
1 stop11h 12mDelta
Deal found 9/13$452
This Delta deal was found by Cheapflights users on 9/12. 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.
Wed 11/125:32 amORD - GCM
1 stop6h 03mDelta
Wed 11/191:50 pmGCM - ORD
2 stops19h 16mDelta
Deal found 9/12$456
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/76:52 amSTL - GCM
1 stop6h 18mAmerican Airlines
Wed 11/121:20 pmGCM - STL
1 stop10h 07mAmerican Airlines
Deal found 9/15$460

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 September 15, 2025.
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

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 11/12

6:05 am-12:35 pm

1 stop5h 30m

George Town Owen Roberts Intl

Thu 11/20

1:30 pm-9:50 pm

1 stop9h 20m

$426

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 11/14

6:55 pm-11:54 am

1 stop15h 59m

George Town Owen Roberts Intl

Fri 11/21

3:43 pm-10:50 pm

1 stop8h 07m

$431

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 11/14

6:55 pm-11:54 am

1 stop15h 59m

George Town Owen Roberts Intl

Sun 11/23

3:36 pm-10:50 pm

1 stop8h 14m

$431

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Mon 1/26

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Wed 1/28

2:00 pm-11:40 pm

1 stop10h 40m

$446

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 12/7

9:40 pm-12:35 pm

2 stops13h 55m

George Town Owen Roberts Intl

Fri 12/12

1:30 pm-12:10 am

2 stops11h 40m

$450

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 12/4

8:49 am-4:30 pm

1 stop6h 41m

George Town Owen Roberts Intl

Tue 12/9

5:45 pm-12:15 am

1 stop7h 30m

$452

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 11/16

7:52 pm-12:35 pm

1 stop15h 43m

George Town Owen Roberts Intl

Fri 11/21

1:50 pm-12:02 am

1 stop11h 12m

$452

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Fri 11/7

6:52 am-2:10 pm

1 stop6h 18m

George Town Owen Roberts Intl

Wed 11/12

1:20 pm-11:07 pm

2 stops10h 47m

$464

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 12/15

7:35 am-4:30 pm

1 stop7h 55m

George Town Owen Roberts Intl

Fri 12/19

2:50 pm-6:04 pm

Nonstop4h 14m

$476

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 11/16

7:52 pm-12:35 pm

1 stop15h 43m

George Town Owen Roberts Intl

Sun 11/23

1:50 pm-12:02 am

1 stop11h 12m

$477

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 36 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, January is the cheapest month in which you can book a flight from Illinois to Cayman Islands (average of $467). Flying from Illinois to Cayman Islands in March is currently the most expensive (average of $594). 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 September 15, 2025.

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 Southwest, JetBlue, and Delta fly from Illinois to Cayman Islands in about 5h 30m. The time it takes to get you to your destination can typically vary by up to 10h 29m. Airlines will cover a distance of 1613 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $124. Air Canada flights start at $136 while deals on JetBlue start at $154 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, January is the cheapest month in which you can book a flight from Illinois to Cayman Islands (average of $467). Flying from Illinois to Cayman Islands in March is currently the most expensive (average of $594). 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

Browse thousands of different options on Cheapflights for your next trip

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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 3 airlines flying from Illinois to Cayman Islands

Discover the top 3 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$530Average$676FlexibilityNo cancel feeOn-time71%
DeltaCheapest$564Average$694FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$587Average$751FlexibilityNo cancel feeOn-time69%

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