$72+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Jan 17 — Jan 241
1 adult, Economy
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Illinois to Grand Cayman
Cheapest flights from Illinois to Grand CaymanExplore 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 December 18, 2025.
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 December 18, 2025.
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/316:05 pmORD - GCM
1 stop16h 30mMultiple Airlines
Wed 1/711:30 amGCM - ORD
1 stop21h 48mMultiple Airlines
Deal found 12/17![Multiple Airlines logo]()
$368
This United Airlines deal was found by Cheapflights users on 12/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Wed 12/312:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 12/17![United Airlines logo]()
$438
This Delta deal was found by Cheapflights users on 12/16. 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.
Wed 12/245:30 amORD - GCM
1 stop6h 06mDelta
Wed 12/313:42 pmGCM - ORD
1 stop9h 20mDelta
Deal found 12/16![Delta logo]()
$452
This American Airlines deal was found by Cheapflights users on 12/18. 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 12/249:24 amORD - GCM
Nonstop4h 11mAmerican Airlines
Wed 12/313:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 12/18![American Airlines logo]()
$463
This United Airlines deal was found by Cheapflights users on 12/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/188:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Thu 12/252:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 12/17![United Airlines logo]()
$468
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/248:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Mon 12/295:10 pmGCM - ORD
1 stop7h 34mUnited Airlines
Deal found 12/16![United Airlines logo]()
$478
This Delta deal was found by Cheapflights users on 12/16. 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.
Thu 12/255:30 amORD - GCM
1 stop7h 57mDelta
Wed 12/311:52 pmGCM - ORD
1 stop11h 10mDelta
Deal found 12/16![Delta logo]()
$482
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/259:24 amORD - GCM
Nonstop4h 11mAmerican Airlines
Wed 12/313:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 12/16![American Airlines logo]()
$493
This Southwest deal was found by Cheapflights users on 12/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/185:50 amMDW - GCM
1 stop5h 45mSouthwest
Thu 12/251:30 pmGCM - MDW
1 stop8h 10mSouthwest
Deal found 12/17![Southwest logo]()
$522
This Delta deal was found by Cheapflights users on 12/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:00 amMDW - GCM
1 stop5h 36mDelta
Wed 12/311:52 pmGCM - MDW
1 stop9h 30mDelta
Deal found 12/17![Delta logo]()
$559
This Delta deal was found by Cheapflights users on 12/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:00 amMDW - GCM
1 stop7h 27mDelta
Wed 12/313:42 pmGCM - MDW
1 stop7h 40mDelta
Deal found 12/17![Delta logo]()
$651
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Sat 12/206:35 pmSTL - GCM
2 stops20h 25mUnited Airlines
Sat 12/275:45 pmGCM - STL
1 stop17h 04mUnited Airlines
Deal found 12/16![United Airlines logo]()
$657
Find 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 December 18, 2025.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $240 (Mytrip) |
One-way from | $72 (Priceline) |
Popular in | December |
Cheapest in | October |
Average price | $827 |
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 December 18, 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
St. LouisGeorge Town
STL - GCM
STLGCM
Lambert-St Louis
Mon 1/26
6:00 am-12:40 pm
1 stop5h 40m
George Town Owen Roberts Intl
Tue 2/3
2:05 pm-8:37 pm
1 stop7h 32m
$352
St. LouisGeorge Town
STL - GCM
STLGCM
Lambert-St Louis
Wed 1/28
6:00 am-12:40 pm
1 stop5h 40m
George Town Owen Roberts Intl
Tue 2/3
2:05 pm-11:37 pm
1 stop10h 32m
$352
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 3/28
3:55 pm-11:10 am
1 stop19h 15m
George Town Owen Roberts Intl
Fri 4/3
12:30 pm-10:03 pm
1 stop9h 33m
$361
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 3/29
4:43 pm-11:10 am
1 stop18h 27m
George Town Owen Roberts Intl
Fri 4/3
12:30 pm-9:55 am
1 stop21h 25m
$361
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Thu 1/15
8:45 pm-12:25 pm
1 stop14h 40m
George Town Owen Roberts Intl
Mon 1/19
1:30 pm-10:05 pm
1 stop9h 35m
$361
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 1/10
4:38 pm-1:53 pm
3 stops20h 15m
George Town Owen Roberts Intl
Sat 1/17
2:34 pm-9:12 am
2 stops19h 38m
$364
St. LouisGeorge Town
STL - GCM
STLGCM
Lambert-St Louis
Mon 2/16
6:25 am-1:45 pm
1 stop6h 20m
George Town Owen Roberts Intl
Mon 2/23
2:50 pm-10:59 pm
1 stop9h 09m
$372
St. LouisGeorge Town
STL - GCM
STLGCM
Lambert-St Louis
Sat 1/24
4:05 pm-12:25 pm
1 stop19h 20m
George Town Owen Roberts Intl
Thu 1/29
1:30 pm-3:29 pm
1 stop26h 59m
$373
St. LouisGeorge Town
STL - GCM
STLGCM
Lambert-St Louis
Sat 1/24
4:05 pm-12:25 pm
1 stop19h 20m
George Town Owen Roberts Intl
Mon 2/2
1:30 pm-3:29 pm
1 stop26h 59m
$373
St. LouisGeorge Town
STL - GCM
STLGCM
Lambert-St Louis
Fri 1/23
9:59 am-12:50 pm
2 stops25h 51m
George Town Owen Roberts Intl
Tue 2/3
2:05 pm-8:37 pm
1 stop7h 32m
$376
Showing 1-10 of 43 results
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, December is the cheapest month in which you can book a flight from Illinois to Grand Cayman (average of $339). Flying from Illinois to Grand Cayman in September is currently the most expensive (average of $650). 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 December 18, 2025.
When flying from Illinois to Grand Cayman, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 41% versus a flight in the morning.
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.
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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.
Top 2 airlines flying from Illinois to Grand Cayman
Discover the top 2 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 December 18, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$680 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$452 | Average$724 | FlexibilityNo cancel fee | On-time71% |