$94+ Cheap flights from Chicago (CHI) 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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Mar 27 — Apr 31
1 adult, Economy
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Find cheap flights from Chicago 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 Chicago to Grand Cayman
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Cheapest flights from Chicago to Grand CaymanExplore the most affordable flight options available from Chicago to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 25, 2026.
Explore the most affordable flight options available from Chicago to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 25, 2026.
This Priceline deal was found by Cheapflights users on 2/23. 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.
Wed 2/258:16 pm
ORD
- GCM
1 stop16h 27m
Spirit Airlines
Sun 3/12:49 pm
GCM
- ORD
1 stop9h 58m
Spirit Airlines
Deal found 2/23![Spirit Airlines logo]()
$458
This Mytrip deal was found by Cheapflights users on 2/22. 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 3/158:00 am
ORD
- GCM
1 stop26h 25m
Multiple Airlines
Sun 3/225:05 pm
GCM
- ORD
1 stop15h 20m
Multiple Airlines
Deal found 2/22![Multiple Airlines logo]()
$459
This Travelocity deal was found by Cheapflights users on 2/22. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:22 pm
ORD
- GCM
2 stops41h 08m
Multiple Airlines
Tue 6/22:05 pm
GCM
- ORD
2 stops20h 12m
Multiple Airlines
Deal found 2/22![Multiple Airlines logo]()
$460
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:02 pm
ORD
- GCM
2 stops21h 03m
Multiple Airlines
Wed 3/118:00 am
GCM
- ORD
1 stop10h 29m
Multiple Airlines
Deal found 2/21![Multiple Airlines logo]()
$461
This Kiwi.com deal was found by Cheapflights users on 2/24. 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.
Fri 3/136:10 pm
ORD
- GCM
1 stop18h 10m
Multiple Airlines
Thu 3/191:52 pm
GCM
- ORD
2 stops10h 21m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$462
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 3/27:23 pm
ORD
- GCM
1 stop19h 42m
Multiple Airlines
Sat 3/78:50 am
GCM
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$463
This Air Canada deal was found by Cheapflights users on 2/24. 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 4/93:45 pm
ORD
- GCM
2 stops18h 25m
Air Canada
Thu 4/1611:55 am
GCM
- ORD
2 stops20h 03m
Air Canada
Deal found 2/24![Air Canada logo]()
$464
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 3/164:51 pm
ORD
- GCM
1 stop23h 14m
Multiple Airlines
Sat 3/211:15 pm
GCM
- ORD
1 stop6h 54m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$465
This Mytrip deal was found by Cheapflights users on 2/24. 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.
Thu 3/125:05 am
ORD
- GCM
1 stop7h 52m
Multiple Airlines
Mon 3/164:45 pm
GCM
- ORD
3 stops30h 32m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$466
This Kiwi.com deal was found by Cheapflights users on 2/22. 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 3/126:00 am
MDW
- GCM
1 stop15h 15m
Multiple Airlines
Thu 3/197:00 am
GCM
- MDW
2 stops12h 47m
Multiple Airlines
Deal found 2/22![Multiple Airlines logo]()
$467
This Mytrip deal was found by Cheapflights users on 2/24. 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.
Wed 3/253:55 pm
ORD
- GCM
1 stop19h 30m
Multiple Airlines
Sat 3/281:15 pm
GCM
- ORD
2 stops18h 46m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$467
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:20 am
ORD
- GCM
1 stop29h 00m
Multiple Airlines
Fri 4/175:05 pm
GCM
- ORD
2 stops21h 15m
Multiple Airlines
Deal found 2/21![Multiple Airlines logo]()
$468
Best flights from Chicago to Grand CaymanDiscover carefully curated flight deals from Chicago to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 25, 2026.
Discover carefully curated flight deals from Chicago to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 25, 2026.
This Delta deal was found by Cheapflights users on 2/22. 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 4/276:00 am
MDW
- GCM
1 stop6h 00m
Delta
Thu 4/301:25 pm
GCM
- MDW
1 stop9h 03m
Delta
Deal found 2/22![Delta logo]()
$499
This Southwest deal was found by Cheapflights users on 2/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:15 pm
MDW
- GCM
2 stops17h 25m
Southwest
Wed 5/271:05 pm
GCM
- MDW
2 stops16h 20m
Southwest
Deal found 2/21![Southwest logo]()
$548
This United Airlines deal was found by Cheapflights users on 2/22. 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.
Sun 3/158:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Sun 3/224:45 pm
GCM
- ORD
1 stop7h 14m
United Airlines
Deal found 2/22![United Airlines logo]()
$561
This Delta deal was found by Cheapflights users on 2/23. 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 3/316:00 am
MDW
- GCM
1 stop5h 47m
Delta
Tue 4/71:12 pm
GCM
- MDW
1 stop9h 19m
Delta
Deal found 2/23![Delta logo]()
$499
This Southwest deal was found by Cheapflights users on 2/23. 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.
Tue 7/216:00 am
ORD
- GCM
1 stop5h 50m
Southwest
Wed 7/2912:45 pm
GCM
- ORD
1 stop11h 10m
Southwest
Deal found 2/23![Southwest logo]()
$559
This United Airlines deal was found by Cheapflights users on 2/23. 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 4/238:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Mon 4/271:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 2/23![United Airlines logo]()
$571
This Delta deal was found by Cheapflights users on 2/21. 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.
Wed 4/15:30 am
ORD
- GCM
1 stop6h 17m
Delta
Sun 4/51:12 pm
GCM
- ORD
1 stop10h 42m
Delta
Deal found 2/21![Delta logo]()
$529
This Southwest deal was found by Cheapflights users on 2/23. 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.
Tue 7/215:10 am
MDW
- GCM
1 stop6h 40m
Southwest
Wed 7/2912:45 pm
GCM
- MDW
2 stops10h 35m
Southwest
Deal found 2/23![Southwest logo]()
$564
This Delta deal was found by Cheapflights users on 2/23. 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 4/106:00 am
MDW
- GCM
1 stop5h 47m
Delta
Thu 4/161:25 pm
GCM
- MDW
1 stop9h 03m
Delta
Deal found 2/23![Delta logo]()
$529
This United Airlines deal was found by Cheapflights users on 2/23. 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 6/276:30 am
ORD
- GCM
1 stop8h 35m
United Airlines
Sat 7/41:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 2/23![United Airlines logo]()
$611
This Southwest deal was found by Cheapflights users on 2/22. 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 4/99:15 pm
MDW
- GCM
2 stops14h 55m
Southwest
Thu 4/161:05 pm
GCM
- MDW
2 stops10h 25m
Southwest
Deal found 2/22![Southwest logo]()
$578
This Delta deal was found by Cheapflights users on 2/21. 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 3/305:30 am
ORD
- GCM
1 stop6h 17m
Delta
Sun 4/51:12 pm
GCM
- ORD
1 stop10h 42m
Delta
Deal found 2/21![Delta logo]()
$560
This United Airlines deal was found by Cheapflights users on 2/21. 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.
Sun 4/58:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Sun 4/121:35 pm
GCM
- ORD
1 stop11h 51m
United Airlines
Deal found 2/21![United Airlines logo]()
$630
This Southwest deal was found by Cheapflights users on 2/22. 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.
Fri 4/179:15 pm
MDW
- GCM
2 stops17h 45m
Southwest
Mon 4/201:05 pm
GCM
- MDW
1 stop11h 00m
Southwest
Deal found 2/22![Southwest logo]()
$588
This United Airlines deal was found by Cheapflights users on 2/24. 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 3/318:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Wed 4/11:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 2/24![United Airlines logo]()
$631
This Southwest deal was found by Cheapflights users on 2/23. 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.
Sat 5/305:30 pm
MDW
- GCM
2 stops18h 25m
Southwest
Sat 6/61:05 pm
GCM
- MDW
1 stop9h 20m
Southwest
Deal found 2/23![Southwest logo]()
$592
This Delta deal was found by Cheapflights users on 2/22. 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 7/296:00 am
ORD
- GCM
1 stop5h 26m
Delta
Sun 8/212:40 pm
GCM
- ORD
1 stop8h 36m
Delta
Deal found 2/22![Delta logo]()
$596
This United Airlines deal was found by Cheapflights users on 2/24. 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 3/258:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Tue 4/71:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 2/24![United Airlines logo]()
$631
This United Airlines deal was found by Cheapflights users on 2/21. 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.
Sun 4/2610:45 pm
ORD
- GCM
1 stop13h 45m
United Airlines
Wed 4/291:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 2/21![United Airlines logo]()
$635
This Delta deal was found by Cheapflights users on 2/21. 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.
Fri 3/276:00 am
MDW
- GCM
1 stop5h 47m
Delta
Mon 3/301:12 pm
GCM
- MDW
1 stop9h 19m
Delta
Deal found 2/21![Delta logo]()
$670
This Southwest deal was found by Cheapflights users on 2/22. 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 3/129:40 pm
MDW
- GCM
2 stops14h 05m
Southwest
Thu 3/1912:40 pm
GCM
- MDW
2 stops11h 25m
Southwest
Deal found 2/22![Southwest logo]()
$702
Last-minute flights from Chicago to Grand CaymanDiscover last-minute flight deals from Chicago to Grand Cayman. Data last updated February 25, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Grand Cayman. Data last updated February 25, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 2/23. 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.
Wed 2/258:16 pm
ORD
- GCM
1 stop16h 27m
Spirit Airlines
Sun 3/12:49 pm
GCM
- ORD
1 stop9h 58m
Spirit Airlines
Deal found 2/23![Spirit Airlines logo]()
$458
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 3/27:23 pm
ORD
- GCM
1 stop19h 42m
Multiple Airlines
Sat 3/78:50 am
GCM
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$463
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:02 pm
ORD
- GCM
2 stops21h 03m
Multiple Airlines
Wed 3/118:00 am
GCM
- ORD
1 stop10h 29m
Multiple Airlines
Deal found 2/21![Multiple Airlines logo]()
$461
This Mytrip deal was found by Cheapflights users on 2/24. 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.
Thu 3/125:05 am
ORD
- GCM
1 stop7h 52m
Multiple Airlines
Mon 3/164:45 pm
GCM
- ORD
3 stops30h 32m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$466
This Kiwi.com deal was found by Cheapflights users on 2/22. 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 3/126:00 am
MDW
- GCM
1 stop15h 15m
Multiple Airlines
Thu 3/197:00 am
GCM
- MDW
2 stops12h 47m
Multiple Airlines
Deal found 2/22![Multiple Airlines logo]()
$467
This Kiwi.com deal was found by Cheapflights users on 2/24. 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.
Fri 3/136:10 pm
ORD
- GCM
1 stop18h 10m
Multiple Airlines
Thu 3/191:52 pm
GCM
- ORD
2 stops10h 21m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$462
This Mytrip deal was found by Cheapflights users on 2/24. 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.
Fri 3/1312:45 pm
ORD
- GCM
3 stops23h 35m
Spirit Airlines
Thu 3/191:52 pm
GCM
- ORD
1 stop9h 25m
Spirit Airlines
Deal found 2/24![Spirit Airlines logo]()
$475
This Mytrip deal was found by Cheapflights users on 2/22. 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 3/158:00 am
ORD
- GCM
1 stop26h 25m
Multiple Airlines
Sun 3/225:05 pm
GCM
- ORD
1 stop15h 20m
Multiple Airlines
Deal found 2/22![Multiple Airlines logo]()
$459
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 3/164:51 pm
ORD
- GCM
1 stop23h 14m
Multiple Airlines
Sat 3/211:15 pm
GCM
- ORD
1 stop6h 54m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$465
This Air Canada deal was found by Cheapflights users on 2/24. 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.
Tue 3/246:04 pm
ORD
- GCM
2 stops41h 21m
Air Canada
Mon 3/3011:25 am
GCM
- ORD
2 stops31h 28m
Air Canada
Deal found 2/24![Air Canada logo]()
$471
This Mytrip deal was found by Cheapflights users on 2/24. 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.
Wed 3/253:55 pm
ORD
- GCM
1 stop19h 30m
Multiple Airlines
Sat 3/281:15 pm
GCM
- ORD
2 stops18h 46m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$467
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 3/256:10 pm
ORD
- GCM
1 stop18h 47m
Multiple Airlines
Sun 3/291:52 pm
GCM
- ORD
2 stops21h 00m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$470
One-way flights from Chicago to Grand CaymanSearch for one-way flight options from Chicago to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated February 25, 2026.
Search for one-way flight options from Chicago to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated February 25, 2026.
This Priceline deal was found by Cheapflights users on 2/22. 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.
Thu 3/125:05 am
ORD
- GCM
1 stop7h 52m
Spirit Airlines
Deal found 2/22![Spirit Airlines logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 2/22. 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 2/2812:06 pm
ORD
- GCM
1 stop24h 37m
Multiple Airlines
Deal found 2/22![Multiple Airlines logo]()
$117
This Air Canada deal was found by Cheapflights users on 2/24. 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 4/236:40 pm
ORD
- GCM
1 stop15h 30m
Air Canada
Deal found 2/24![Air Canada logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 2/23. 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 3/256:10 pm
ORD
- GCM
1 stop18h 47m
Spirit Airlines
Deal found 2/23![Spirit Airlines logo]()
$127
This FlightHub deal was found by Cheapflights users on 2/24. 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 5/33:50 pm
ORD
- GCM
1 stop19h 35m
Air Canada
Deal found 2/24![Air Canada logo]()
$128
This Air Canada deal was found by Cheapflights users on 2/24. 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.
Wed 4/226:21 pm
ORD
- GCM
2 stops39h 49m
Air Canada
Deal found 2/24![Air Canada logo]()
$130
This Air Canada deal was found by Cheapflights users on 2/24. 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 4/63:45 pm
ORD
- GCM
2 stops19h 25m
Air Canada
Deal found 2/24![Air Canada logo]()
$131
This Air Canada deal was found by Cheapflights users on 2/23. 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 3/268:40 pm
ORD
- GCM
1 stop14h 45m
Air Canada
Deal found 2/23![Air Canada logo]()
$132
This Air Canada deal was found by Cheapflights users on 2/21. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/208:20 pm
ORD
- GCM
1 stop15h 10m
Air Canada
Deal found 2/21![Air Canada logo]()
$133
This Air Canada deal was found by Cheapflights users on 2/24. 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.
Tue 4/216:01 pm
ORD
- GCM
2 stops40h 54m
Air Canada
Deal found 2/24![Air Canada logo]()
$134
This Trip.com deal was found by Cheapflights users on 2/23. 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.
Thu 3/126:00 am
MDW
- GCM
1 stop15h 15m
Multiple Airlines
Deal found 2/23![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 5/37:30 am
MDW
- GCM
1 stop10h 30m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$148
Find flight deals from Chicago to Grand Cayman
Keep the following information in mind while searching for Chicago to Grand Cayman flight deals. Data was last updated February 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $458 (Mytrip) |
One-way from | $94 (Priceline) |
Popular in | December |
Cheapest in | February |
Average price | $527 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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 25, 2026.
Use the filters below to find and compare flights from Chicago to Grand Cayman that are best for you.
Fly from
Chicago
Fly to
Grand Cayman
Route
Depart
Return
Price
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Mon 4/27
6:00 am-12:00 pm
1 stop6h 00m
George Town Owen Roberts Intl
Thu 4/30
1:25 pm-10:28 pm
1 stop9h 03m
$499
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Tue 3/31
6:00 am-11:47 am
1 stop5h 47m
George Town Owen Roberts Intl
Tue 4/7
1:12 pm-10:31 pm
1 stop9h 19m
$499
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 4/1
5:30 am-11:47 am
1 stop6h 17m
George Town Owen Roberts Intl
Sun 4/5
1:12 pm-11:54 pm
1 stop10h 42m
$529
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Fri 4/10
6:00 am-11:47 am
1 stop5h 47m
George Town Owen Roberts Intl
Thu 4/16
1:25 pm-10:28 pm
1 stop9h 03m
$529
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Fri 5/22
9:15 pm-2:40 pm
2 stops17h 25m
George Town Owen Roberts Intl
Wed 5/27
1:05 pm-5:25 am
2 stops16h 20m
$548
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 7/21
6:00 am-11:50 am
1 stop5h 50m
George Town Owen Roberts Intl
Wed 7/29
12:45 pm-11:55 pm
1 stop11h 10m
$559
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Mon 3/30
5:30 am-11:47 am
1 stop6h 17m
George Town Owen Roberts Intl
Sun 4/5
1:12 pm-11:54 pm
1 stop10h 42m
$560
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 3/15
8:45 am-12:45 pm
Nonstop4h 00m
George Town Owen Roberts Intl
Sun 3/22
4:45 pm-11:59 pm
1 stop7h 14m
$561
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Tue 7/21
5:10 am-11:50 am
1 stop6h 40m
George Town Owen Roberts Intl
Wed 7/29
12:45 pm-11:20 pm
2 stops10h 35m
$564
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Thu 4/23
8:45 am-12:45 pm
Nonstop4h 00m
George Town Owen Roberts Intl
Mon 4/27
1:50 pm-6:13 pm
Nonstop4h 23m
$571
Showing 1-10 of 41 results
Best time to book a flight from Chicago to Grand Cayman
Have a flexible travel schedule? Discover the best time to fly to Grand Cayman from Chicago with our price prediction graph.
ORD-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 Chicago to Grand Cayman
CHI-zzLAW
ORD-GCM
MDW-GCM
What is the cheapest month to book a flight from Chicago to Grand Cayman?
Currently, December is the cheapest month in which you can book a flight from Chicago to Grand Cayman (average of $322). Flying from Chicago to Grand Cayman in September is currently the most expensive (average of $661). 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 CHI to LAW?
Find hourly flight availability from Chicago 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 25, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Grand Cayman as you normally would.
Weekly flight availability from Chicago to Grand Cayman
Explore weekly flight availability from Chicago to Grand Cayman. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 25, 2026.
The most flights from CHI to zzLAW are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).
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 February 25, 2026.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Chicago to Grand Cayman. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Chicago 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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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 Chicago to Grand Cayman by cabin class
Find flights from Chicago to Grand Cayman, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Grand Cayman flights
Browse other Chicago and Grand Cayman flight options. Last updated on February 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Chicago to Grand Cayman
Discover the top 2 airlines that operate flights from Chicago 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 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$610 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$438 | Average$669 | FlexibilityNo cancel fee | On-time71% |