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Cayman Islands

$101+ 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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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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 November 3, 2025.

This Priceline deal was found by Cheapflights users on 10/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/67:10 amORD - GCM
1 stop8h 45mSpirit Airlines
Sat 12/135:56 pmGCM - ORD
1 stop7h 13mSpirit Airlines
Deal found 10/31$271
This United Airlines deal was found by Cheapflights users on 10/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/298:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Sat 12/62:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 10/31$338
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/125:00 amORD - GCM
1 stop5h 59mAmerican Airlines
Fri 12/193:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 11/2$342
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Sun 12/145:00 amORD - GCM
1 stop6h 00mAmerican Airlines
Sun 12/213:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 11/2$347
This Delta deal was found by Cheapflights users on 11/2. 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 12/246:00 amMDW - GCM
1 stop5h 36mDelta
Sun 12/283:42 pmGCM - MDW
1 stop7h 40mDelta
Deal found 11/2$352
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/29:07 pmORD - GCM
2 stops14h 17mAmerican Airlines
Tue 12/91:25 pmGCM - ORD
2 stops11h 14mAmerican Airlines
Deal found 11/2$357
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Wed 12/249:24 amORD - GCM
Nonstop4h 11mAmerican Airlines
Wed 12/313:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 11/2$363
This United Airlines deal was found by Cheapflights users on 10/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/138:50 amORD - GCM
1 stop6h 40mUnited Airlines
Sat 11/152:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 10/31$374
This Delta deal was found by Cheapflights users on 11/1. 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.
Tue 12/166:00 amMDW - GCM
1 stop5h 40mDelta
Tue 12/233:42 pmGCM - MDW
1 stop7h 40mDelta
Deal found 11/1$385
This Delta deal was found by Cheapflights users on 11/2. 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.
Thu 11/136:00 amMDW - GCM
1 stop5h 35mDelta
Sat 11/151:50 pmGCM - MDW
1 stop10h 50mDelta
Deal found 11/2$414
This Southwest deal was found by Cheapflights users on 11/1. 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.
Tue 12/165:05 amMDW - GCM
1 stop6h 30mSouthwest
Tue 12/231:30 pmGCM - MDW
2 stops10h 35mSouthwest
Deal found 11/1$441
This Delta deal was found by Cheapflights users on 11/2. 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 12/246:00 amMDW - GCM
1 stop5h 36mDelta
Tue 12/301:52 pmGCM - MDW
1 stop9h 30mDelta
Deal found 11/2$443

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 November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$271
(Priceline)

One-way from

$101
(Expedia)

Popular in

December

Cheapest in

October

Average price

$804

Good round-trip deal

$448 or less

Good one-way deal

$582 or less
Provider with most accurate pricing for Chicago (CHI)-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-George Town Owen Roberts Intl flights.
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From Illinois to Cayman Islands
Search Deals
One-way flight from Illinois to Cayman Islands
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($72 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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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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 November 3, 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

Sat 11/29

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Sat 12/6

2:50 pm-6:04 pm

Nonstop4h 14m

$338

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 12/6

9:59 am-3:09 pm

Nonstop4h 10m

George Town Owen Roberts Intl

Sat 12/13

4:09 pm-7:19 pm

Nonstop4h 10m

$338

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/24

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Sat 1/31

2:50 pm-6:04 pm

Nonstop4h 14m

$342

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/24

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Sun 2/1

2:50 pm-6:04 pm

Nonstop4h 14m

$342

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 12/14

5:30 am-12:35 pm

1 stop6h 05m

George Town Owen Roberts Intl

Sun 12/21

1:52 pm-9:14 pm

1 stop8h 22m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 12/12

5:40 pm-11:29 am

1 stop16h 49m

George Town Owen Roberts Intl

Fri 12/19

12:55 pm-10:34 pm

1 stop10h 39m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 12/29

7:59 pm-12:36 pm

1 stop15h 37m

George Town Owen Roberts Intl

Wed 12/31

1:52 pm-7:38 pm

1 stop6h 46m

$352

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 12/24

6:00 am-12:36 pm

1 stop5h 36m

George Town Owen Roberts Intl

Wed 12/31

1:52 pm-10:22 pm

1 stop9h 30m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 12/5

7:35 am-4:30 pm

1 stop7h 55m

George Town Owen Roberts Intl

Wed 12/10

5:45 pm-7:42 am

1 stop14h 57m

$352

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 12/24

6:00 am-12:36 pm

1 stop5h 36m

George Town Owen Roberts Intl

Sun 12/28

3:42 pm-10:22 pm

1 stop7h 40m

$352

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 56 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 $356). 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 November 3, 2025.

It’s optimal to fly from Illinois to Cayman Islands at noon. By choosing this option you can save up to 41% on the cost of your flight, compared to a flight in the morning.

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 United Airlines, American Airlines, and Delta fly from Illinois to Cayman Islands in about 4h. The time it takes to get you to your destination can typically vary by up to 1h 36m. 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 $101. Air Canada flights start at $136 while deals on Southwest start at $155 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 $356). 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

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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$434Average$721FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$488Average$692FlexibilityNo cancel feeOn-time71%
DeltaCheapest$564Average$694FlexibilityNo cancel feeOn-timeN/A

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