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Cayman Islands

$180+ 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
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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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 November 21, 2024.

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 21, 2024.

This Delta deal was found by Cheapflights users on 11/21. 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 12/96:00 amSTL - GCM
1 stop5h 42mDelta
Tue 12/171:57 pmGCM - STL
1 stop7h 46mDelta
Deal found 11/21$517
This American Airlines deal was found by Cheapflights users on 11/21. 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.
Wed 12/115:29 pmSTL - GCM
2 stops17h 31mAmerican Airlines
Tue 12/171:40 pmGCM - STL
1 stop6h 50mAmerican Airlines
Deal found 11/21$522
This United Airlines deal was found by Cheapflights users on 11/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/128:40 amSTL - GCM
1 stop6h 45mUnited Airlines
Mon 12/165:35 pmGCM - STL
1 stop17h 15mUnited Airlines
Deal found 11/21$540
This Southwest deal was found by Cheapflights users on 11/19. 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 12/96:00 amMDW - GCM
1 stop5h 55mSouthwest
Thu 12/121:50 pmGCM - MDW
2 stops9h 30mSouthwest
Deal found 11/19$575
This Delta deal was found by Cheapflights users on 11/21. 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.
Tue 12/247:05 amORD - GCM
1 stop6h 27mDelta
Tue 12/313:47 pmGCM - ORD
1 stop9h 09mDelta
Deal found 11/21$618
This Delta deal was found by Cheapflights users on 11/21. 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.
Tue 12/246:00 amMDW - GCM
1 stop7h 32mDelta
Tue 12/313:47 pmGCM - MDW
1 stop7h 19mDelta
Deal found 11/21$618
This American Airlines deal was found by Cheapflights users on 11/21. 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 1/71:40 pmGCM - ORD
1 stop6h 46mAmerican Airlines
Deal found 11/21$623
This Kiwi.com deal was found by Cheapflights users on 11/20. 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 12/196:00 amMDW - GCM
1 stop14h 20mMultiple Airlines
Thu 12/264:45 pmGCM - MDW
2 stops21h 39mMultiple Airlines
Deal found 11/20$669
This CheapOair deal was found by Cheapflights users on 11/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/36:10 pmORD - GCM
2 stops42h 30mAir Canada
Sun 12/84:00 pmGCM - ORD
1 stop22h 11mAir Canada
Deal found 11/21$689
This United Airlines deal was found by Cheapflights users on 11/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/198:48 amORD - GCM
Nonstop3h 57mUnited Airlines
Thu 12/262:50 pmGCM - ORD
Nonstop4h 16mUnited Airlines
Deal found 11/20$694
This United deal was found by Cheapflights users on 11/20. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/255:39 pmMLI - GCM
2 stops21h 46mUnited Airlines
Wed 1/15:35 pmGCM - MLI
2 stops17h 43mUnited Airlines
Deal found 11/20$700
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Sun 12/88:02 pmORD - GCM
1 stop19h 08mMultiple Airlines
Sun 12/152:00 pmGCM - ORD
1 stop30h 07mMultiple Airlines
Deal found 11/20$734

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 2,612,795 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Mon 1/13

6:00 am-12:44 pm

1 stop5h 44m

George Town Owen Roberts Intl

Thu 1/16

2:09 pm-11:37 pm

1 stop10h 28m

$440

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Mon 1/13

3:41 pm-12:00 pm

2 stops19h 19m

George Town Owen Roberts Intl

Thu 1/16

3:35 pm-10:28 pm

1 stop7h 53m

$445

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 2/19

7:25 am-4:10 pm

1 stop7h 45m

George Town Owen Roberts Intl

Fri 2/28

4:45 pm-8:44 am

1 stop16h 59m

$488

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 1/16

1:34 pm-11:40 am

1 stop21h 06m

George Town Owen Roberts Intl

Tue 1/21

11:30 am-12:45 pm

2 stops26h 15m

$498

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 2/25

5:45 am-12:55 pm

1 stop6h 10m

George Town Owen Roberts Intl

Sat 3/1

2:10 pm-11:15 pm

2 stops10h 05m

$532

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Thu 12/12

8:40 am-4:25 pm

1 stop6h 45m

George Town Owen Roberts Intl

Mon 12/16

5:35 pm-9:50 am

1 stop17h 15m

$540

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 2/1

6:30 pm-12:35 pm

1 stop17h 05m

George Town Owen Roberts Intl

Wed 2/5

1:00 pm-7:19 pm

1 stop7h 19m

$588

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 2/23

6:00 am-12:44 pm

1 stop5h 44m

George Town Owen Roberts Intl

Fri 2/28

2:09 pm-10:20 pm

1 stop9h 11m

$588

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 1/29

4:00 pm-1:40 pm

1 stop20h 40m

George Town Owen Roberts Intl

Sun 2/2

4:00 pm-1:11 pm

1 stop22h 11m

$592

MolineGeorge Town

MLI - GCM

MLIGCM

Moline Quad-City

Thu 1/23

5:00 am-12:35 pm

1 stop6h 35m

George Town Owen Roberts Intl

Sun 2/2

1:40 pm-10:22 pm

1 stop9h 42m

$592

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

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 June is currently the most expensive (average of $560). 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 21, 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.

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 November 21, 2024.
To help decide which airline to fly from Illinois to Cayman Islands, see what other customers have to say about Delta, American Airlines 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
8.1
Very good
5,005 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,172 reviews
Southwest
8.1
Very good
5,005 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,811 reviews
Southwest
8.1
Very good
5,005 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
5,005 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $240. Sun Country Air flights start at $272 while deals on Delta start at $297 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 June is currently the most expensive (average of $560). 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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$348Average$476FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$368Average$625FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$420Average$671FlexibilityNo cancel feeOn-time69%
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