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Cayman Islands

$179+ 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$430
(American Airlines)

One-way from

$179
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$655

Good round-trip deal

$619 or less

Good one-way deal

$288 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. 11% potential increase in price ($83 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/11. 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 10/15:28 amSTL - GCM
1 stop5h 42mAmerican Airlines
Tue 10/78:30 amGCM - STL
1 stop14h 39mAmerican Airlines
Deal found 6/11$430
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Tue 7/81:43 pmORD - GCM
1 stop26h 27mMultiple Airlines
Mon 7/144:45 pmGCM - ORD
1 stop23h 26mMultiple Airlines
Deal found 6/11$467
This Southwest deal was found by Cheapflights users on 6/11. 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.
Sat 11/17:20 pmMDW - GCM
2 stops17h 15mSouthwest
Thu 11/61:30 pmGCM - MDW
1 stop10h 20mSouthwest
Deal found 6/11$489
This United Airlines deal was found by Cheapflights users on 6/11. 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 7/266:33 amSTL - GCM
1 stop6h 57mUnited Airlines
Sat 8/24:45 pmGCM - STL
1 stop16h 43mUnited Airlines
Deal found 6/11$510
This Air Canada deal was found by Cheapflights users on 6/10. 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.
Sun 10/196:20 pmORD - GCM
1 stop17h 35mAir Canada
Thu 10/3012:35 pmGCM - ORD
1 stop24h 16mAir Canada
Deal found 6/10$515
This Delta deal was found by Cheapflights users on 6/11. 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 12/106:00 amORD - GCM
1 stop5h 37mDelta
Tue 1/132:00 pmGCM - ORD
1 stop10h 54mDelta
Deal found 6/11$520
This Delta deal was found by Cheapflights users on 6/10. 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 10/196:00 amMDW - GCM
1 stop5h 42mDelta
Thu 10/301:02 pmGCM - MDW
1 stop8h 42mDelta
Deal found 6/10$520
This American Airlines deal was found by Cheapflights users on 6/11. 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 9/148:44 pmORD - GCM
1 stop14h 41mAmerican Airlines
Fri 9/1912:10 pmGCM - ORD
2 stops11h 02mAmerican Airlines
Deal found 6/11$524
This Southwest deal was found by Cheapflights users on 6/11. 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 11/196:05 amORD - GCM
1 stop5h 30mSouthwest
Tue 12/21:30 pmGCM - ORD
1 stop9h 20mSouthwest
Deal found 6/11$543
This American Airlines deal was found by Cheapflights users on 6/11. 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 7/226:37 pmMLI - GCM
2 stops16h 33mAmerican Airlines
Sun 7/272:10 pmGCM - MLI
2 stops25h 39mAmerican Airlines
Deal found 6/11$578
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Wed 12/106:00 amORD - GCM
1 stop9h 25mUnited Airlines
Mon 1/122:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 6/11$600
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Fri 9/56:21 amMDW - GCM
1 stop9h 39mMultiple Airlines
Tue 9/911:30 amGCM - MDW
2 stops11h 28mMultiple Airlines
Deal found 6/10$654

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 June 12, 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

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Wed 10/1

5:28 am-11:10 am

1 stop5h 42m

George Town Owen Roberts Intl

Tue 10/7

8:30 am-11:09 pm

1 stop14h 39m

$430

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 7/8

1:43 pm-4:10 pm

1 stop26h 27m

George Town Owen Roberts Intl

Mon 7/14

4:45 pm-4:11 pm

1 stop23h 26m

$467

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 11/1

7:20 pm-12:35 pm

2 stops17h 15m

George Town Owen Roberts Intl

Thu 11/6

1:30 pm-10:50 pm

1 stop10h 20m

$489

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Sat 7/26

6:33 am-1:30 pm

1 stop6h 57m

George Town Owen Roberts Intl

Sat 8/2

4:45 pm-9:28 am

1 stop16h 43m

$510

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 10/19

6:20 pm-11:55 am

1 stop17h 35m

George Town Owen Roberts Intl

Sun 10/26

12:35 pm-10:58 am

1 stop22h 23m

$515

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 10/20

6:00 am-11:42 am

1 stop5h 42m

George Town Owen Roberts Intl

Fri 10/24

1:02 pm-9:12 pm

1 stop8h 10m

$520

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 10/19

6:00 am-11:42 am

1 stop5h 42m

George Town Owen Roberts Intl

Thu 10/30

1:02 pm-9:44 pm

1 stop8h 42m

$520

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 9/14

8:44 pm-11:25 am

1 stop14h 41m

George Town Owen Roberts Intl

Fri 9/19

12:10 pm-11:12 pm

2 stops11h 02m

$524

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 11/19

6:05 am-12:35 pm

1 stop5h 30m

George Town Owen Roberts Intl

Tue 12/2

1:30 pm-9:50 pm

1 stop9h 20m

$543

MolineGeorge Town

MLI - GCM

MLIGCM

Moline Quad-City

Tue 7/22

6:37 pm-11:10 am

2 stops16h 33m

George Town Owen Roberts Intl

Sun 7/27

2:10 pm-3:49 pm

2 stops25h 39m

$578

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 26 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 June 12, 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.

Reviews of airlines servicing Cayman Islands

Get insights into the airlines that provide service to Cayman Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Cayman Islands. Reviews last updated June 12, 2025.
To help decide which airline to fly from Illinois to Cayman Islands, see what other customers have to say about Southwest, Delta and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
WestJet
7.2
Good
2,868 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

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

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $190. American Airlines flights start at $216 while deals on Air Canada start at $237 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

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Alternative routes for Illinois to Cayman Islands

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$446Average$670FlexibilityNo cancel feeOn-time71%
DeltaCheapest$463Average$668FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$522Average$721FlexibilityNo cancel feeOn-time69%

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