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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Dec 27 — Jan 31
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Cheap flight deals from Illinois to Cayman Islands

Discover tips and strategies to find the most affordable flight options for your journey from Illinois (USIL) to Cayman Islands (KY0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 22, 2024.

Round-trip from

$526
(Delta)

One-way from

$179
(Kiwi.com)
From Illinois to Cayman Islands
One-way flight from Illinois to Cayman Islands

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 December 22, 2024.

This Delta deal was found by Cheapflights users on 12/22. 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 12/256:00 amSTL - GCM
1 stop5h 27mDelta
Mon 12/303:47 pmGCM - STL
1 stop8h 53mDelta
Deal found 12/22$659
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Tue 12/315:07 pmORD - GCM
1 stop22h 03mMultiple Airlines
Tue 1/711:30 amGCM - ORD
1 stop29h 42mMultiple Airlines
Deal found 12/21$704
This Southwest deal was found by Cheapflights users on 12/21. 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 12/256:10 amSTL - GCM
1 stop5h 45mSouthwest
Fri 12/271:50 pmGCM - STL
1 stop8h 15mSouthwest
Deal found 12/21$724
This American Airlines deal was found by Cheapflights users on 12/22. 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 12/251:45 pmSTL - GCM
2 stops21h 15mAmerican Airlines
Mon 12/301:35 pmGCM - STL
2 stops9h 53mAmerican Airlines
Deal found 12/22$740
This Air Canada deal was found by Cheapflights users on 12/22. 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 12/223:50 pmSTL - GCM
1 stop20h 50mAir Canada
Thu 12/264:00 pmGCM - STL
1 stop24h 06mAir Canada
Deal found 12/22$775
This Southwest deal was found by Cheapflights users on 12/20. 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 12/216:15 amORD - GCM
1 stop6h 05mSouthwest
Sat 12/282:15 pmGCM - ORD
1 stop9h 20mSouthwest
Deal found 12/20$784
This United deal was found by Cheapflights users on 12/22. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/226:25 amSTL - GCM
1 stop6h 20mUnited Airlines
Thu 12/265:40 pmGCM - STL
2 stops18h 07mUnited Airlines
Deal found 12/22$809
This American Airlines deal was found by Cheapflights users on 12/21. 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 12/315:02 amORD - GCM
2 stops8h 28mAmerican Airlines
Tue 1/73:15 pmGCM - ORD
1 stop18h 44mAmerican Airlines
Deal found 12/21$844
This Air Canada deal was found by Cheapflights users on 12/21. 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 12/228:25 pmORD - GCM
1 stop16h 15mAir Canada
Sun 12/294:00 pmGCM - ORD
1 stop17h 57mAir Canada
Deal found 12/21$855
This Delta deal was found by Cheapflights users on 12/21. 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 12/307:05 amORD - GCM
1 stop6h 27mDelta
Wed 1/13:47 pmGCM - ORD
1 stop9h 09mDelta
Deal found 12/21$858
This Delta deal was found by Cheapflights users on 12/22. 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 12/255:58 amMLI - GCM
1 stop5h 29mDelta
Wed 1/11:52 pmGCM - MLI
1 stop7h 39mDelta
Deal found 12/22$858
This Kiwi.com deal was found by Cheapflights users on 12/20. 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.
Thu 12/265:52 pmMDW - GCM
1 stop20h 53mMultiple Airlines
Sun 12/297:00 amGCM - MDW
1 stop7h 36mMultiple Airlines
Deal found 12/20$904

Find flights from Illinois to Cayman Islands within your budget

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Fri 1/31

6:00 am-12:38 pm

1 stop5h 38m

George Town Owen Roberts Intl

Tue 2/11

2:04 pm-11:36 pm

1 stop10h 32m

$526

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Fri 1/31

5:23 am-12:35 pm

1 stop6h 12m

George Town Owen Roberts Intl

Sat 2/15

5:40 pm-9:52 am

2 stops17h 12m

$531

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Thu 1/30

3:50 pm-1:40 pm

1 stop20h 50m

George Town Owen Roberts Intl

Sun 2/16

4:00 pm-3:06 pm

1 stop24h 06m

$568

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 1/28

1:55 pm-1:40 pm

2 stops46h 45m

George Town Owen Roberts Intl

Sun 2/2

4:00 pm-1:11 pm

1 stop22h 11m

$578

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 2/5

3:56 pm-6:40 pm

2 stops25h 44m

George Town Owen Roberts Intl

Wed 2/12

11:30 am-10:37 am

1 stop24h 07m

$580

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 3/19

3:14 pm-6:45 pm

1 stop27h 31m

George Town Owen Roberts Intl

Mon 3/24

2:00 pm-11:00 pm

1 stop9h 00m

$583

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 5/3

6:40 am-12:10 pm

1 stop5h 30m

George Town Owen Roberts Intl

Thu 5/8

12:45 pm-10:40 pm

1 stop9h 55m

$584

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 2/10

7:04 am-2:30 pm

1 stop6h 26m

George Town Owen Roberts Intl

Fri 3/7

1:45 pm-9:39 pm

1 stop8h 54m

$598

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 3/25

6:00 am-11:25 am

1 stop5h 25m

George Town Owen Roberts Intl

Tue 4/1

12:50 pm-10:27 pm

1 stop9h 37m

$598

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Sat 2/1

8:15 am-4:35 pm

1 stop7h 20m

George Town Owen Roberts Intl

Wed 2/12

2:25 pm-11:30 pm

1 stop10h 05m

$616

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

Showing 1-10 of 30 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.

Travel insights for flights from Illinois to Cayman Islands

Get recent, data-driven insights about flights from Illinois to Cayman Islands including ideal travel times, pricing trends, and more.

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 December 22, 2024.

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.

Weekly flight availability from Illinois to Cayman Islands

Explore weekly flight availability from Illinois to Cayman Islands. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 22, 2024.

The most flights from USIL to KY0 are scheduled on a Saturday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 December 22, 2024.
To help decide which airline to fly from Illinois to Cayman Islands, see what other customers have to say about American Airlines, United Airlines and Delta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.1
Very good
4,804 reviews

Boarding

8.2

Comfort

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.1
Very good
4,804 reviews
8.1
Very good
4,804 reviews

Boarding

8.2

Comfort

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
8,594 reviews
8.1
Very good
4,804 reviews

Boarding

8.2

Comfort

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
9,028 reviews
8.1
Very good
4,804 reviews

Boarding

8.2

Comfort

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.3
Good
2,812 reviews
8.1
Very good
4,804 reviews

Boarding

8.2

Comfort

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.2
Good
10,000 reviews
8.1
Very good
4,804 reviews

Boarding

8.2

Comfort

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 American Airlines, which is currently one of the cheapest options available, starting at $211. Air Canada flights start at $214 while deals on Sun Country Air start at $233 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.

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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$351Average$501FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$367Average$625FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$429Average$683FlexibilityNo cancel feeOn-time69%
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