$176+ 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
jun. 23 — jun. 301
1 adult, Economy
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1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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
Keep the following information in mind while searching for Illinois to Grand Cayman flight deals. Data was last updated junio 18, 2025.
Round-trip from | $454 (Delta) |
|---|---|
One-way from | $176 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $657 |
Find 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 junio 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 junio 18, 2025.
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/76:00 amSTL - GCM
1 stop5h 22mDelta
jue. 8/1412:52 pmGCM - STL
1 stop8h 35mDelta
Deal found 6/18![Delta logo]()
$454
This American Airlines deal was found by Cheapflights users on 6/16. 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.
sáb. 10/187:00 pmSTL - GCM
1 stop16h 05mAmerican Airlines
sáb. 10/258:30 amGCM - STL
1 stop14h 39mAmerican Airlines
Deal found 6/16![American Airlines logo]()
$457
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
mar. 7/11:43 pmORD - GCM
1 stop26h 27mMultiple Airlines
mar. 7/811:30 amGCM - ORD
1 stop28h 41mMultiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$463
This lol.travel deal was found by Cheapflights users on 6/18. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/75:30 pmSTL - GCM
2 stops19h 00mUnited Airlines
jue. 8/141:35 pmGCM - STL
2 stops22h 52mUnited Airlines
Deal found 6/18![United Airlines logo]()
$503
This American Airlines deal was found by Cheapflights users on 6/16. 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.
mar. 12/238:10 amORD - GCM
Nonstop3h 46mAmerican Airlines
vie. 12/262:15 pmGCM - ORD
1 stop8h 16mAmerican Airlines
Deal found 6/16![American Airlines logo]()
$515
This United Airlines deal was found by Cheapflights users on 6/16. 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.
jue. 10/306:00 amORD - GCM
1 stop9h 25mUnited Airlines
mar. 11/45:35 pmGCM - ORD
1 stop15h 06mUnited Airlines
Deal found 6/16![United Airlines logo]()
$520
This Delta deal was found by Cheapflights users on 6/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/126:00 amMDW - GCM
1 stop5h 42mDelta
dom. 10/191:02 pmGCM - MDW
1 stop8h 42mDelta
Deal found 6/15![Delta logo]()
$545
This Delta deal was found by Cheapflights users on 6/17. 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.
sáb. 12/66:00 amORD - GCM
1 stop5h 37mDelta
jue. 12/112:02 pmGCM - ORD
1 stop8h 10mDelta
Deal found 6/17![Delta logo]()
$555
This Southwest deal was found by Cheapflights users on 6/16. 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.
dom. 7/205:25 pmORD - GCM
2 stops18h 25mSouthwest
vie. 7/2512:45 pmGCM - ORD
2 stops20h 40mSouthwest
Deal found 6/16![Southwest logo]()
$597
This Southwest deal was found by Cheapflights users on 6/17. 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.
sáb. 9/66:15 amMDW - GCM
1 stop5h 55mSouthwest
sáb. 9/131:10 pmGCM - MDW
1 stop7h 10mSouthwest
Deal found 6/17![Southwest logo]()
$626
This Air Canada deal was found by Cheapflights users on 6/16. 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.
mié. 11/198:25 pmORD - GCM
1 stop14h 55mAir Canada
vie. 11/281:35 pmGCM - ORD
1 stop20h 22mAir Canada
Deal found 6/16![Air Canada logo]()
$636
This Mytrip deal was found by Cheapflights users on 6/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/2311:24 amSTL - GCM
3 stops33h 56mMultiple Airlines
mié. 7/3011:30 amGCM - STL
3 stops31h 11mMultiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$640
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 junio 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
jue. 8/7
6:00 am-11:22 am
1 stop5h 22m
George Town Owen Roberts Intl
jue. 8/14
12:52 pm-9:27 pm
1 stop8h 35m
$454
St. LouisGeorge Town
STL - GCM
STLGCM
Lambert-St Louis
sáb. 10/18
7:00 pm-11:05 am
1 stop16h 05m
George Town Owen Roberts Intl
sáb. 10/25
8:30 am-11:09 pm
1 stop14h 39m
$457
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
mar. 7/1
1:43 pm-4:10 pm
1 stop26h 27m
George Town Owen Roberts Intl
mar. 7/8
11:30 am-4:11 pm
1 stop28h 41m
$463
St. LouisGeorge Town
STL - GCM
STLGCM
Lambert-St Louis
jue. 8/7
5:30 pm-12:30 pm
2 stops19h 00m
George Town Owen Roberts Intl
jue. 8/14
1:35 pm-12:27 pm
2 stops22h 52m
$503
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
sáb. 8/30
6:30 pm-11:25 am
1 stop16h 55m
George Town Owen Roberts Intl
jue. 9/4
12:10 pm-9:22 pm
1 stop9h 12m
$570
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
sáb. 8/30
6:00 am-11:37 am
1 stop5h 37m
George Town Owen Roberts Intl
jue. 9/4
12:50 pm-9:26 pm
1 stop8h 36m
$595
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
dom. 8/3
6:00 am-12:30 pm
1 stop6h 30m
George Town Owen Roberts Intl
vie. 8/8
1:35 pm-9:33 pm
1 stop7h 58m
$595
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
dom. 7/20
5:25 pm-11:50 am
2 stops18h 25m
George Town Owen Roberts Intl
vie. 7/25
12:45 pm-9:25 am
2 stops20h 40m
$597
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
mié. 7/23
5:35 am-11:22 am
1 stop5h 47m
George Town Owen Roberts Intl
mié. 7/30
12:37 pm-9:30 pm
1 stop8h 53m
$620
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
sáb. 9/6
6:15 am-12:10 pm
1 stop5h 55m
George Town Owen Roberts Intl
sáb. 9/13
1:10 pm-8:20 pm
1 stop7h 10m
$626
Showing 1-10 of 25 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, 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 junio 18, 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.
Reviews of airlines servicing Grand Cayman
Get insights into the airlines that provide service to Grand Cayman. 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 Grand Cayman. Reviews last updated junio 18, 2025.
Read reviews from past customers who have flown Southwest, Delta and United Airlines from Illinois to Grand Cayman. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.6
Comfort
8.0
Food
7.1
Boarding
8.2
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Entertainment
7.6
Comfort
8.0
Food
7.1
Boarding
8.2
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Entertainment
7.6
Comfort
8.0
Food
7.1
Boarding
8.2
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Entertainment
7.6
Comfort
8.0
Food
7.1
Boarding
8.2
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Entertainment
7.6
Comfort
8.0
Food
7.1
Boarding
8.2
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Entertainment
7.6
Comfort
8.0
Food
7.1
Boarding
8.2
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
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 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 junio 18, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$446 | Average$676 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$463 | Average$628 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$522 | Average$722 | FlexibilityNo cancel fee | On-time69% |