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Cayman Islands

$174+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$425
(American Airlines)

One-way from

$174
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$621

Good round-trip deal

$515 or less

Good one-way deal

$358 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 ($60 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 July 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 July 31, 2025.

This American Airlines deal was found by Cheapflights users on 7/30. 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.
Mon 8/255:26 amSTL - GCM
1 stop7h 46mAmerican Airlines
Sat 8/302:15 pmGCM - STL
1 stop8h 59mAmerican Airlines
Deal found 7/30$425
This Air Canada deal was found by Cheapflights users on 7/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/158:25 pmORD - GCM
1 stop15h 30mAir Canada
Mon 10/2012:50 pmGCM - ORD
2 stops21h 01mAir Canada
Deal found 7/28$451
This American Airlines deal was found by Cheapflights users on 7/29. 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 8/306:30 pmORD - GCM
1 stop16h 55mAmerican Airlines
Thu 9/412:25 pmGCM - ORD
1 stop8h 02mAmerican Airlines
Deal found 7/29$452
This Mytrip deal was found by Cheapflights users on 7/29. 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.
Fri 9/1210:27 amORD - GCM
1 stop10h 53mMultiple Airlines
Fri 9/194:45 pmGCM - ORD
1 stop16h 33mMultiple Airlines
Deal found 7/29$461
This Delta deal was found by Cheapflights users on 7/29. 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.
Sat 8/306:00 amMDW - GCM
1 stop5h 37mDelta
Thu 9/412:50 pmGCM - MDW
1 stop8h 36mDelta
Deal found 7/29$477
This Southwest deal was found by Cheapflights users on 7/29. 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.
Mon 12/155:05 amMDW - GCM
1 stop6h 30mSouthwest
Sat 12/204:10 pmGCM - MDW
1 stop8h 10mSouthwest
Deal found 7/29$481
This Southwest deal was found by Cheapflights users on 7/30. 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.
Fri 11/73:15 pmSTL - GCM
2 stops20h 45mSouthwest
Tue 11/111:30 pmGCM - STL
2 stops9h 40mSouthwest
Deal found 7/30$485
This Expedia deal was found by Cheapflights users on 7/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/158:50 amORD - GCM
2 stops28h 41mJetBlue
Sat 11/221:57 pmGCM - ORD
1 stop22h 59mJetBlue
Deal found 7/30$489
This Air Canada deal was found by Cheapflights users on 7/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/294:05 pmSTL - GCM
1 stop19h 15mAir Canada
Fri 12/51:30 pmGCM - STL
1 stop26h 59mAir Canada
Deal found 7/31$502
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Sun 12/147:35 amORD - GCM
1 stop7h 55mUnited Airlines
Fri 12/192:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 7/31$510
This Delta deal was found by Cheapflights users on 7/29. 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 12/227:59 pmORD - GCM
1 stop15h 31mDelta
Tue 12/301:55 pmGCM - ORD
1 stop11h 03mDelta
Deal found 7/29$520
This Southwest deal was found by Cheapflights users on 7/29. 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 12/36:05 amORD - GCM
1 stop5h 30mSouthwest
Sun 12/71:30 pmGCM - ORD
1 stop9h 20mSouthwest
Deal found 7/29$529

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 July 31, 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

Mon 8/25

5:26 am-1:12 pm

1 stop7h 46m

George Town Owen Roberts Intl

Sat 8/30

2:15 pm-11:14 pm

1 stop8h 59m

$425

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 1/12

7:55 pm-12:55 pm

2 stops16h 00m

George Town Owen Roberts Intl

Wed 1/21

1:50 pm-9:00 pm

1 stop8h 10m

$438

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 1/12

6:05 am-12:55 pm

1 stop5h 50m

George Town Owen Roberts Intl

Wed 1/21

1:50 pm-9:50 pm

1 stop9h 00m

$448

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 10/15

8:25 pm-11:55 am

1 stop15h 30m

George Town Owen Roberts Intl

Mon 10/20

12:50 pm-9:51 am

2 stops21h 01m

$451

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 8/30

6:30 pm-11:25 am

1 stop16h 55m

George Town Owen Roberts Intl

Thu 9/4

12:25 pm-8:27 pm

1 stop8h 02m

$452

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 9/12

10:27 am-9:20 pm

1 stop10h 53m

George Town Owen Roberts Intl

Fri 9/19

4:45 pm-9:18 am

1 stop16h 33m

$461

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 8/30

6:00 am-11:37 am

1 stop5h 37m

George Town Owen Roberts Intl

Thu 9/4

12:50 pm-9:26 pm

1 stop8h 36m

$477

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Fri 11/7

3:15 pm-1:00 pm

2 stops20h 45m

George Town Owen Roberts Intl

Tue 11/11

1:30 pm-10:10 pm

2 stops9h 40m

$485

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 11/15

8:50 am-2:31 pm

2 stops28h 41m

George Town Owen Roberts Intl

Sat 11/22

1:57 pm-11:56 am

1 stop22h 59m

$489

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Sat 11/29

4:05 pm-12:20 pm

1 stop19h 15m

George Town Owen Roberts Intl

Fri 12/5

1:30 pm-3:29 pm

1 stop26h 59m

$502

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 31 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 July 31, 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 July 31, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Illinois to the Cayman Islands by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
WestJet
7.2
Good
2,978 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 Air Canada, which is currently one of the cheapest options available, starting at $178. Delta flights start at $199 while deals on American Airlines start at $260 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

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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$463Average$668FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$512Average$683FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$573Average$732FlexibilityNo cancel feeOn-time69%

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