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Grand Cayman

$136+ Cheap flights from Illinois to Grand Cayman

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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Illinois to Grand Cayman

Keep the following information in mind while searching for Illinois to Grand Cayman flight deals. Data was last updated September 17, 2025.

Round-trip from

$311
(Priceline)

One-way from

$136
(Air Canada)

Popular in

December

Cheapest in

October

Average price

$569
From Illinois to Grand Cayman
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One-way flight from Illinois to Grand Cayman
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Highest demand for flights based on searches. 8% potential increase in price ($59 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 September 2025
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Find flight deals from Illinois to Grand Cayman

Cheapest flights from Illinois to Grand Cayman
Explore the most affordable flight options available from Illinois to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:59 pmORD - GCM
1 stop16h 01mSpirit Airlines
Sat 12/1311:55 amGCM - ORD
1 stop10h 05mSpirit Airlines
Deal found 9/15$311
This Air Canada deal was found by Cheapflights users on 9/16. 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.
Thu 11/273:35 pmORD - GCM
2 stops19h 50mAir Canada
Tue 12/21:30 pmGCM - ORD
1 stop20h 43mAir Canada
Deal found 9/16$394
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 12/41:35 pmORD - GCM
1 stop21h 00mMultiple Airlines
Sun 12/1411:55 amGCM - ORD
1 stop8h 26mMultiple Airlines
Deal found 9/17$419
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 12/31:35 pmORD - GCM
1 stop21h 00mMultiple Airlines
Sun 12/1411:55 amGCM - ORD
1 stop12h 47mMultiple Airlines
Deal found 9/16$420
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 12/41:35 pmORD - GCM
1 stop21h 00mMultiple Airlines
Thu 12/1111:55 amGCM - ORD
1 stop10h 05mMultiple Airlines
Deal found 9/17$424
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Wed 12/31:35 pmORD - GCM
1 stop21h 00mMultiple Airlines
Thu 12/1111:55 amGCM - ORD
1 stop10h 05mMultiple Airlines
Deal found 9/17$425
This Booking.com deal was found by Cheapflights users on 9/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/26:05 pmORD - GCM
2 stops41h 20mAir Canada
Tue 12/91:30 pmGCM - ORD
2 stops24h 21mAir Canada
Deal found 9/16$426
This Air Canada deal was found by Cheapflights users on 9/16. 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.
Mon 12/89:10 pmORD - GCM
1 stop14h 15mAir Canada
Thu 12/111:30 pmGCM - ORD
1 stop24h 31mAir Canada
Deal found 9/16$430
This Southwest deal was found by Cheapflights users on 9/16. 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 12/35:05 amMDW - GCM
1 stop6h 30mSouthwest
Wed 12/101:30 pmGCM - MDW
1 stop7h 00mSouthwest
Deal found 9/16$446
This Delta deal was found by Cheapflights users on 9/16. 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 amSTL - GCM
1 stop5h 35mDelta
Thu 10/2312:55 pmGCM - STL
1 stop8h 33mDelta
Deal found 9/16$446
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Fri 11/76:52 amSTL - GCM
1 stop6h 18mAmerican Airlines
Wed 11/121:20 pmGCM - STL
1 stop10h 07mAmerican Airlines
Deal found 9/15$460
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Fri 10/316:15 amSTL - GCM
1 stop9h 15mUnited Airlines
Fri 11/75:45 pmGCM - STL
2 stops19h 43mUnited Airlines
Deal found 9/16$464

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Grand Cayman 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 September 17, 2025.
Use the filters below to find and compare flights from Illinois to Grand Cayman that are best for you.

Fly from

Illinois

Fly to

Grand Cayman

Route

Depart

Return

Price

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 11/27

3:35 pm-12:25 pm

2 stops19h 50m

George Town Owen Roberts Intl

Tue 12/2

1:30 pm-9:13 am

1 stop20h 43m

$394

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/3

1:35 pm-11:35 am

1 stop21h 00m

George Town Owen Roberts Intl

Sun 12/14

11:55 am-7:21 pm

1 stop8h 26m

$420

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 12/4

1:35 pm-11:35 am

1 stop21h 00m

George Town Owen Roberts Intl

Sat 12/13

11:55 am-9:00 pm

1 stop10h 05m

$424

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Mon 1/26

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Wed 1/28

2:00 pm-11:40 pm

1 stop10h 40m

$438

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Mon 1/26

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Thu 1/29

2:00 pm-8:39 pm

1 stop7h 39m

$438

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 12/7

10:05 pm-9:15 pm

2 stops22h 10m

George Town Owen Roberts Intl

Sun 12/14

11:55 am-11:42 pm

1 stop12h 47m

$439

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Mon 1/26

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Tue 2/3

2:00 pm-11:40 pm

1 stop10h 40m

$439

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/3

6:05 am-12:35 pm

1 stop5h 30m

George Town Owen Roberts Intl

Wed 12/10

1:30 pm-9:50 pm

1 stop9h 20m

$446

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 9/29

5:30 am-11:36 am

1 stop6h 06m

George Town Owen Roberts Intl

Fri 10/3

12:52 pm-9:25 pm

1 stop8h 33m

$446

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Sun 10/19

6:00 am-11:35 am

1 stop5h 35m

George Town Owen Roberts Intl

Thu 10/23

12:55 pm-9:28 pm

1 stop8h 33m

$446

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 40 results
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Best time to book a flight from Illinois to Grand Cayman

Have a flexible travel schedule? Discover the best time to fly to Grand Cayman 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 Grand Cayman

What is the cheapest month to book a flight from Illinois to Grand Cayman?

Currently, January is the cheapest month in which you can book a flight from Illinois to Grand Cayman (average of $467). Flying from Illinois to Grand Cayman 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 LAW?

Find hourly flight availability from Illinois to Grand Cayman. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Grand Cayman as you normally would.

Related info for your journey

Find useful and relevant information for your journey from Illinois to Grand Cayman. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Illinois to Grand Cayman?

    Airlines like Air Canada, Delta, and Southwest fly from Illinois to Grand Cayman in about 5h 35m. The time it takes to get you to your destination can typically vary by up to 14h 15m. The distance from Illinois to Grand Cayman is about 1448 mi. This flight may include one or multiple stops.

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

    $136 is the cheapest one-way deal found within the past few days, from Air Canada. You may also be able to find cheap deals on JetBlue and Southwest, with prices starting from $163 and $171, respectively.

  • Can I find deals for flights from Illinois to Grand Cayman that include hotel bookings?

    Yes. In addition to deals on Illinois to Grand Cayman flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Grand Cayman?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Grand Cayman.

  • Can I find deals for business class flights from Illinois to Grand Cayman?

    Yes. Cheapflights offers flight deals from Illinois to Grand Cayman 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 Grand Cayman?

    Currently, January is the cheapest month in which you can book a flight from Illinois to Grand Cayman (average of $467). Flying from Illinois to Grand Cayman 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 Grand Cayman

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 Grand Cayman

Discover the top 3 airlines that operate flights from Illinois to Grand Cayman. 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$530Average$676FlexibilityNo cancel feeOn-time71%
DeltaCheapest$564Average$694FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$587Average$751FlexibilityNo cancel feeOn-time69%

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