$59+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Mar 5 — Mar 121
1 adult, Economy
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Find cheap flights from Illinois to Grand Cayman with Cheapflights
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
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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 February 3, 2026.
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 February 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/265:15 am
ORD
- GCM
1 stop7h 28m
Multiple Airlines
Sun 3/12:49 pm
GCM
- ORD
2 stops27h 34m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$357
This Mytrip deal was found by Cheapflights users on 2/2. 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.
Sat 2/216:51 pm
ORD
- GCM
2 stops17h 52m
Spirit Airlines
Thu 2/262:49 pm
GCM
- ORD
2 stops10h 51m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$358
This Delta deal was found by Cheapflights users on 2/2. 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 3/25:55 am
MLI
- GCM
1 stop5h 34m
Delta
Tue 3/101:12 pm
GCM
- MLI
1 stop9h 18m
Delta
Deal found 2/2![Delta logo]()
$359
This Orbitz deal was found by Cheapflights users on 2/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/64:15 pm
ORD
- GCM
1 stop18h 55m
Multiple Airlines
Thu 4/91:52 pm
GCM
- ORD
1 stop9h 25m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$362
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/258:16 pm
ORD
- GCM
1 stop16h 27m
Multiple Airlines
Sun 3/12:49 pm
GCM
- ORD
2 stops24h 41m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$364
This Mytrip deal was found by Cheapflights users on 2/3. 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.
Sun 3/157:17 am
ORD
- GCM
1 stop5h 40m
Spirit Airlines
Thu 3/191:52 pm
GCM
- ORD
2 stops20h 28m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/195:15 am
ORD
- GCM
1 stop7h 28m
Multiple Airlines
Wed 2/2511:30 am
GCM
- ORD
2 stops21h 24m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 3/15:15 am
ORD
- GCM
1 stop7h 28m
Multiple Airlines
Sat 3/78:50 am
GCM
- ORD
2 stops24h 32m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$367
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Tue 3/316:00 am
STL
- GCM
1 stop6h 30m
United Airlines
Tue 4/71:35 pm
GCM
- STL
1 stop8h 53m
United Airlines
Deal found 2/1![United Airlines logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Sat 2/2112:06 pm
ORD
- GCM
1 stop24h 37m
Multiple Airlines
Wed 2/2511:30 am
GCM
- ORD
2 stops21h 24m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/1811:51 am
ORD
- GCM
2 stops22h 44m
Multiple Airlines
Thu 2/262:49 pm
GCM
- ORD
1 stop9h 16m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/16:15 am
MDW
- GCM
1 stop28h 20m
Multiple Airlines
Sun 3/81:49 pm
GCM
- MDW
2 stops29h 58m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$371
Best flights from Illinois to Grand CaymanDiscover carefully curated flight deals from Illinois to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
Discover carefully curated flight deals from Illinois to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
This Delta deal was found by Cheapflights users on 2/2. 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 3/25:55 am
MLI
- GCM
1 stop5h 34m
Delta
Tue 3/101:12 pm
GCM
- MLI
1 stop9h 18m
Delta
Deal found 2/2![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 1/31. 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 3/185:00 am
STL
- GCM
1 stop7h 45m
United Airlines
Wed 3/251:50 pm
GCM
- STL
1 stop7h 52m
United Airlines
Deal found 1/31![United Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 2/2. 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 3/319:35 am
STL
- GCM
2 stops9h 40m
American Airlines
Tue 4/77:45 am
GCM
- STL
1 stop14h 39m
American Airlines
Deal found 2/2![American Airlines logo]()
$372
This Southwest deal was found by Cheapflights users on 2/3. 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.
Sun 3/16:05 am
MDW
- GCM
1 stop5h 50m
Southwest
Wed 3/41:50 pm
GCM
- MDW
1 stop8h 10m
Southwest
Deal found 2/3![Southwest logo]()
$384
This Air Canada deal was found by Cheapflights users on 2/1. 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.
Sat 4/184:05 pm
STL
- GCM
1 stop18h 50m
Air Canada
Sat 5/212:25 pm
GCM
- STL
1 stop23h 41m
Air Canada
Deal found 2/1![Air Canada logo]()
$396
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Sat 3/146:00 am
MDW
- GCM
2 stops8h 50m
Multiple Airlines
Thu 3/197:00 am
GCM
- MDW
1 stop6h 41m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$419
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Tue 3/316:00 am
STL
- GCM
1 stop6h 30m
United Airlines
Tue 4/71:35 pm
GCM
- STL
1 stop8h 53m
United Airlines
Deal found 2/1![United Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 1/31. 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 3/257:00 am
STL
- GCM
1 stop7h 25m
American Airlines
Mon 3/303:50 pm
GCM
- STL
1 stop17h 05m
American Airlines
Deal found 1/31![American Airlines logo]()
$392
This United Airlines deal was found by Cheapflights users on 2/1. 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 4/236:30 am
STL
- GCM
1 stop6h 15m
United Airlines
Mon 4/271:35 pm
GCM
- STL
1 stop8h 53m
United Airlines
Deal found 2/1![United Airlines logo]()
$372
This American Airlines deal was found by Cheapflights users on 1/31. 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 3/195:12 am
STL
- GCM
1 stop9h 13m
American Airlines
Tue 3/243:30 pm
GCM
- STL
1 stop7h 52m
American Airlines
Deal found 1/31![American Airlines logo]()
$392
This Southwest deal was found by Cheapflights users on 2/3. 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 3/25:30 am
MDW
- GCM
1 stop6h 25m
Southwest
Thu 3/51:40 pm
GCM
- MDW
1 stop7h 35m
Southwest
Deal found 2/3![Southwest logo]()
$435
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Sat 3/146:00 am
MDW
- GCM
2 stops8h 50m
Multiple Airlines
Tue 3/174:25 pm
GCM
- MDW
1 stop17h 40m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$437
This Delta deal was found by Cheapflights users on 2/2. 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 2/175:25 am
ORD
- GCM
1 stop6h 04m
Delta
Fri 2/271:54 pm
GCM
- ORD
1 stop11h 02m
Delta
Deal found 2/2![Delta logo]()
$469
This American Airlines deal was found by Cheapflights users on 2/3. 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 3/317:05 am
STL
- GCM
2 stops12h 10m
American Airlines
Mon 4/63:50 pm
GCM
- STL
1 stop17h 04m
American Airlines
Deal found 2/3![American Airlines logo]()
$397
This Delta deal was found by Cheapflights users on 2/2. 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 5/66:00 am
MDW
- GCM
1 stop6h 00m
Delta
Wed 5/131:19 pm
GCM
- MDW
1 stop7h 50m
Delta
Deal found 2/2![Delta logo]()
$473
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Mon 3/26:00 am
MLI
- GCM
1 stop7h 35m
American Airlines
Tue 3/1012:00 pm
GCM
- MLI
1 stop8h 59m
American Airlines
Deal found 2/1![American Airlines logo]()
$410
This Delta deal was found by Cheapflights users on 2/2. 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 5/46:00 am
MDW
- GCM
1 stop6h 00m
Delta
Wed 5/131:19 pm
GCM
- MDW
1 stop7h 50m
Delta
Deal found 2/2![Delta logo]()
$473
This United Airlines deal was found by Cheapflights users on 2/2. 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.
Mon 4/68:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Thu 4/91:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 2/2![United Airlines logo]()
$491
This Delta deal was found by Cheapflights users on 2/2. 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 5/56:00 am
MDW
- GCM
1 stop6h 00m
Delta
Wed 5/131:19 pm
GCM
- MDW
1 stop7h 50m
Delta
Deal found 2/2![Delta logo]()
$473
This Delta deal was found by Cheapflights users on 2/2. 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 5/66:00 am
MDW
- GCM
1 stop6h 00m
Delta
Tue 5/121:19 pm
GCM
- MDW
1 stop7h 50m
Delta
Deal found 2/2![Delta logo]()
$473
This Delta deal was found by Cheapflights users on 2/2. 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 2/169:34 am
MDW
- GCM
2 stops25h 55m
Delta
Tue 2/241:54 pm
GCM
- MDW
1 stop9h 39m
Delta
Deal found 2/2![Delta logo]()
$474
This Delta deal was found by Cheapflights users on 2/2. 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 2/229:34 am
MDW
- GCM
2 stops25h 55m
Delta
Thu 2/261:54 pm
GCM
- MDW
1 stop9h 37m
Delta
Deal found 2/2![Delta logo]()
$474
This Delta deal was found by Cheapflights users on 2/2. 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 5/55:04 pm
ORD
- GCM
2 stops18h 56m
Delta
Tue 5/121:19 pm
GCM
- ORD
2 stops21h 08m
Delta
Deal found 2/2![Delta logo]()
$478
This Delta deal was found by Cheapflights users on 2/3. 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 5/107:05 pm
ORD
- GCM
2 stops16h 49m
Delta
Fri 5/151:19 pm
GCM
- ORD
2 stops18h 39m
Delta
Deal found 2/3![Delta logo]()
$478
This Delta deal was found by Cheapflights users on 2/3. 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 5/125:20 pm
ORD
- GCM
2 stops18h 34m
Delta
Thu 5/141:19 pm
GCM
- ORD
2 stops18h 39m
Delta
Deal found 2/3![Delta logo]()
$478
This Delta deal was found by Cheapflights users on 2/1. 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 2/245:25 am
ORD
- GCM
1 stop6h 04m
Delta
Sat 2/2812:25 pm
GCM
- ORD
1 stop12h 31m
Delta
Deal found 2/1![Delta logo]()
$499
This Delta deal was found by Cheapflights users on 1/31. 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 4/265:10 am
ORD
- GCM
1 stop6h 50m
Delta
Wed 4/291:25 pm
GCM
- ORD
1 stop8h 00m
Delta
Deal found 1/31![Delta logo]()
$505
This Delta deal was found by Cheapflights users on 2/2. 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 5/257:45 pm
ORD
- GCM
1 stop16h 09m
Delta
Wed 6/31:19 pm
GCM
- ORD
1 stop10h 40m
Delta
Deal found 2/2![Delta logo]()
$507
This Delta deal was found by Cheapflights users on 2/2. 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 5/510:49 am
ORD
- GCM
2 stops25h 11m
Delta
Sun 5/101:19 pm
GCM
- ORD
1 stop8h 30m
Delta
Deal found 2/2![Delta logo]()
$508
This Delta deal was found by Cheapflights users on 2/3. 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.
Sat 5/96:00 am
ORD
- GCM
1 stop5h 54m
Delta
Wed 5/131:19 pm
GCM
- ORD
2 stops21h 08m
Delta
Deal found 2/3![Delta logo]()
$508
Last-minute flights from Illinois to Grand CaymanDiscover last-minute flight deals from Illinois to Grand Cayman. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Grand Cayman. Data last updated February 3, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/1811:51 am
ORD
- GCM
2 stops22h 44m
Multiple Airlines
Thu 2/262:49 pm
GCM
- ORD
1 stop9h 16m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/195:15 am
ORD
- GCM
1 stop7h 28m
Multiple Airlines
Wed 2/2511:30 am
GCM
- ORD
2 stops21h 24m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$366
This Mytrip deal was found by Cheapflights users on 2/2. 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.
Sat 2/216:51 pm
ORD
- GCM
2 stops17h 52m
Spirit Airlines
Thu 2/262:49 pm
GCM
- ORD
2 stops10h 51m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Sat 2/2112:06 pm
ORD
- GCM
1 stop24h 37m
Multiple Airlines
Wed 2/2511:30 am
GCM
- ORD
2 stops21h 24m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/258:16 pm
ORD
- GCM
1 stop16h 27m
Multiple Airlines
Sun 3/12:49 pm
GCM
- ORD
2 stops24h 41m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/265:15 am
ORD
- GCM
1 stop7h 28m
Multiple Airlines
Sun 3/12:49 pm
GCM
- ORD
2 stops27h 34m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 3/15:15 am
ORD
- GCM
1 stop7h 28m
Multiple Airlines
Sat 3/78:50 am
GCM
- ORD
2 stops24h 32m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/16:15 am
MDW
- GCM
1 stop28h 20m
Multiple Airlines
Sun 3/81:49 pm
GCM
- MDW
2 stops29h 58m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 2/2. 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 3/25:55 am
MLI
- GCM
1 stop5h 34m
Delta
Tue 3/101:12 pm
GCM
- MLI
1 stop9h 18m
Delta
Deal found 2/2![Delta logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Mon 3/211:33 am
ORD
- GCM
1 stop8h 42m
Multiple Airlines
Sun 3/81:49 pm
GCM
- ORD
2 stops21h 07m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$371
This Mytrip deal was found by Cheapflights users on 2/3. 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.
Sun 3/157:17 am
ORD
- GCM
1 stop5h 40m
Spirit Airlines
Thu 3/191:52 pm
GCM
- ORD
2 stops20h 28m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$365
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Tue 3/316:00 am
STL
- GCM
1 stop6h 30m
United Airlines
Tue 4/71:35 pm
GCM
- STL
1 stop8h 53m
United Airlines
Deal found 2/1![United Airlines logo]()
$367
One-way flights from Illinois to Grand CaymanSearch for one-way flight options from Illinois to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
Search for one-way flight options from Illinois to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
This Orbitz deal was found by Cheapflights users on 1/31. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:16 pm
ORD
- GCM
1 stop16h 27m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$59
This FlightHub deal was found by Cheapflights users on 2/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/15:15 am
ORD
- GCM
1 stop7h 28m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/48:16 pm
ORD
- GCM
1 stop16h 27m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 4/291:27 pm
ORD
- GCM
1 stop23h 16m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$90
This Delta deal was found by Cheapflights users on 2/2. 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 2/236:00 am
STL
- GCM
1 stop5h 29m
Delta
Deal found 2/2![Delta logo]()
$106
This Trip.com deal was found by Cheapflights users on 2/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/211:33 am
ORD
- GCM
1 stop8h 42m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$111
This Trip.com deal was found by Cheapflights users on 2/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/315:05 am
ORD
- GCM
1 stop7h 40m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$113
This Priceline deal was found by Cheapflights users on 2/1. 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.
Sun 3/155:05 am
ORD
- GCM
1 stop7h 52m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/155:15 am
ORD
- GCM
1 stop7h 28m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$117
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Mon 2/239:37 am
STL
- GCM
2 stops9h 38m
American Airlines
Deal found 2/1![American Airlines logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/116:15 am
MDW
- GCM
2 stops30h 28m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$128
This Gotogate deal was found by Cheapflights users on 2/2. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/207:30 am
STL
- GCM
1 stop28h 00m
Air Canada
Deal found 2/2![Air Canada logo]()
$138
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 February 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $357 (Kiwi.com) |
One-way from | $59 (Orbitz) |
Popular in | December |
Cheapest in | October |
Average price | $570 |
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 February 3, 2026.
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
MolineGeorge Town
MLI - GCM
MLIGCM
Moline Quad-City
Mon 3/2
5:55 am-12:29 pm
1 stop5h 34m
George Town Owen Roberts Intl
Tue 3/10
1:12 pm-10:30 pm
1 stop9h 18m
$359
St. LouisGeorge Town
STL - GCM
STLGCM
Lambert-St Louis
Wed 3/18
5:00 am-12:45 pm
1 stop7h 45m
George Town Owen Roberts Intl
Wed 3/25
1:50 pm-9:42 pm
1 stop7h 52m
$367
St. LouisGeorge Town
STL - GCM
STLGCM
Lambert-St Louis
Tue 3/31
6:00 am-12:30 pm
1 stop6h 30m
George Town Owen Roberts Intl
Tue 4/7
1:35 pm-10:28 pm
1 stop8h 53m
$367
St. LouisGeorge Town
STL - GCM
STLGCM
Lambert-St Louis
Tue 3/31
9:35 am-7:15 pm
2 stops9h 40m
George Town Owen Roberts Intl
Tue 4/7
7:45 am-10:24 pm
1 stop14h 39m
$372
St. LouisGeorge Town
STL - GCM
STLGCM
Lambert-St Louis
Thu 4/23
6:30 am-12:45 pm
1 stop6h 15m
George Town Owen Roberts Intl
Mon 4/27
1:35 pm-10:28 pm
1 stop8h 53m
$372
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Sun 3/1
6:05 am-12:55 pm
1 stop5h 50m
George Town Owen Roberts Intl
Wed 3/4
1:50 pm-9:00 pm
1 stop8h 10m
$384
St. LouisGeorge Town
STL - GCM
STLGCM
Lambert-St Louis
Wed 3/25
7:00 am-2:25 pm
1 stop7h 25m
George Town Owen Roberts Intl
Mon 3/30
3:50 pm-8:55 am
1 stop17h 05m
$392
St. LouisGeorge Town
STL - GCM
STLGCM
Lambert-St Louis
Thu 3/19
5:12 am-2:25 pm
1 stop9h 13m
George Town Owen Roberts Intl
Tue 3/24
3:30 pm-11:22 pm
1 stop7h 52m
$392
St. LouisGeorge Town
STL - GCM
STLGCM
Lambert-St Louis
Sat 4/18
4:05 pm-10:55 am
1 stop18h 50m
George Town Owen Roberts Intl
Sat 5/2
12:25 pm-12:06 pm
1 stop23h 41m
$396
St. LouisGeorge Town
STL - GCM
STLGCM
Lambert-St Louis
Tue 3/31
7:05 am-7:15 pm
2 stops12h 10m
George Town Owen Roberts Intl
Mon 4/6
3:50 pm-8:54 am
1 stop17h 04m
$397
Showing 1-10 of 55 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.
ORD-GCM
MLI-GCM
STL-GCM
MDW-GCM
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
USIL-zzLAW
ORD-GCM
MLI-GCM
STL-GCM
MDW-GCM
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 $322). 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 February 3, 2026.
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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.
Complete your trip
Complete your trip to Grand Cayman by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Illinois to Grand Cayman by cabin class
Find flights from Illinois to Grand Cayman, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Illinois and Grand Cayman flights
Browse other Illinois and Grand Cayman flight options. Last updated on February 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Grand Cayman
Find the right flight back to Illinois after your stay in Grand Cayman
Illinois to Grand Cayman flights
Consider these flights traveling from Illinois to Grand Cayman.
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 February 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$622 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$438 | Average$700 | FlexibilityNo cancel fee | On-time71% |