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Cayman Islands

$169+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$434
(Delta)

One-way from

$195
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$648

Good round-trip deal

$735 or less

Good one-way deal

$313 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
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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 ($62 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 April 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 April 30, 2025.

This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/36:00 amSTL - GCM
1 stop5h 25mDelta
Fri 8/812:40 pmGCM - STL
1 stop9h 01mDelta
Deal found 4/27$434
This American Airlines deal was found by Cheapflights users on 4/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/35:20 amSTL - GCM
1 stop6h 02mAmerican Airlines
Fri 8/812:25 pmGCM - STL
2 stops19h 40mAmerican Airlines
Deal found 4/27$438
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/43:11 pmORD - GCM
1 stop20h 29mMultiple Airlines
Wed 10/811:30 amGCM - ORD
1 stop11h 17mMultiple Airlines
Deal found 4/29$464
This United Airlines deal was found by Cheapflights users on 4/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/86:00 amSTL - GCM
1 stop6h 30mUnited Airlines
Sun 5/111:35 pmGCM - STL
1 stop6h 57mUnited Airlines
Deal found 4/28$484
This Air Canada deal was found by Cheapflights users on 4/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/18:25 pmORD - GCM
1 stop15h 30mAir Canada
Thu 6/512:50 pmGCM - ORD
1 stop9h 15mAir Canada
Deal found 4/29$511
This Air Canada deal was found by Cheapflights users on 4/28. 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.
Sun 6/81:30 pmSTL - GCM
2 stops22h 25mAir Canada
Thu 6/1212:50 pmGCM - STL
1 stop23h 46mAir Canada
Deal found 4/28$524
This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/46:00 pmMDW - GCM
2 stops17h 35mSouthwest
Mon 12/81:30 pmGCM - MDW
2 stops16h 35mSouthwest
Deal found 4/28$542
This United Airlines deal was found by Cheapflights users on 4/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:45 amMLI - GCM
2 stops8h 50mUnited Airlines
Fri 12/125:35 pmGCM - MLI
2 stops28h 23mUnited Airlines
Deal found 4/28$542
This American Airlines deal was found by Cheapflights users on 4/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/64:16 pmMLI - GCM
1 stop18h 49mAmerican Airlines
Fri 12/121:40 pmGCM - MLI
1 stop9h 05mAmerican Airlines
Deal found 4/28$548
This Southwest deal was found by Cheapflights users on 4/29. 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.
Sat 9/66:00 amORD - GCM
1 stop6h 10mSouthwest
Sat 9/131:10 pmGCM - ORD
1 stop8h 20mSouthwest
Deal found 4/29$576
This Delta deal was found by Cheapflights users on 4/29. 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 7/145:35 amORD - GCM
1 stop5h 50mDelta
Tue 7/2212:40 pmGCM - ORD
1 stop8h 50mDelta
Deal found 4/29$610
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/36:00 amMDW - GCM
1 stop5h 25mDelta
Fri 8/812:40 pmGCM - MDW
1 stop9h 01mDelta
Deal found 4/27$610

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 April 30, 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

Sun 8/3

6:00 am-11:25 am

1 stop5h 25m

George Town Owen Roberts Intl

Fri 8/8

12:40 pm-9:41 pm

1 stop9h 01m

$434

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Sun 8/3

5:20 am-11:22 am

1 stop6h 02m

George Town Owen Roberts Intl

Fri 8/8

12:25 pm-8:05 am

2 stops19h 40m

$438

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 10/4

3:11 pm-11:40 am

1 stop20h 29m

George Town Owen Roberts Intl

Wed 10/8

11:30 am-10:47 pm

1 stop11h 17m

$464

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 6/1

8:25 pm-11:55 am

1 stop15h 30m

George Town Owen Roberts Intl

Thu 6/5

12:50 pm-10:05 pm

1 stop9h 15m

$511

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Sun 6/8

1:30 pm-11:55 am

2 stops22h 25m

George Town Owen Roberts Intl

Thu 6/12

12:50 pm-12:36 pm

1 stop23h 46m

$524

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 7/18

9:45 pm-10:35 am

1 stop12h 50m

George Town Owen Roberts Intl

Mon 7/21

12:45 pm-11:40 pm

1 stop10h 55m

$562

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 9/6

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

Sat 9/13

1:10 pm-9:30 pm

1 stop8h 20m

$576

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 7/14

5:35 am-11:25 am

1 stop5h 50m

George Town Owen Roberts Intl

Wed 7/23

12:40 pm-9:30 pm

1 stop8h 50m

$610

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 8/3

6:00 am-11:25 am

1 stop5h 25m

George Town Owen Roberts Intl

Fri 8/8

12:40 pm-9:41 pm

1 stop9h 01m

$610

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 5/28

5:00 am-11:10 am

1 stop6h 10m

George Town Owen Roberts Intl

Tue 6/3

12:10 pm-11:56 pm

2 stops11h 46m

$614

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 27 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 April 30, 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 April 30, 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
4,295 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,929 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
WestJet
7.2
Good
2,826 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 $197. Southwest flights start at $231 while deals on Delta start at $289 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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$446Average$684FlexibilityNo cancel feeOn-time71%
DeltaCheapest$463Average$668FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$501Average$705FlexibilityNo cancel feeOn-time69%

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