$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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
may. 2 — may. 91
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Grand Cayman with Cheapflights
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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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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 abril 2, 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 abril 2, 2026.
This Travelocity deal was found by Cheapflights users on 4/1. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 6/206:04 pm
ORD
- GCM
2 stops41h 21m
Air Canada
jue. 6/2512:25 pm
GCM
- ORD
1 stop28h 32m
Air Canada
Deal found 4/1![Air Canada logo]()
$338
This FlightHub deal was found by Cheapflights users on 3/30. 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.
sáb. 4/45:05 am
ORD
- GCM
1 stop7h 15m
Spirit Airlines
jue. 4/91:52 pm
GCM
- ORD
1 stop9h 25m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$339
This Expedia deal was found by Cheapflights users on 3/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/59:55 am
ORD
- GCM
1 stop24h 05m
Air Canada
lun. 6/812:25 pm
GCM
- ORD
1 stop20h 40m
Air Canada
Deal found 3/31![Air Canada logo]()
$345
This Expedia deal was found by Cheapflights users on 3/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/125:05 am
ORD
- GCM
1 stop7h 52m
Multiple Airlines
jue. 4/1611:55 am
GCM
- ORD
1 stop25h 10m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$346
This Travelocity deal was found by Cheapflights users on 3/30. 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.
dom. 6/218:40 pm
ORD
- GCM
1 stop14h 45m
Air Canada
lun. 6/2912:25 pm
GCM
- ORD
1 stop24h 57m
Air Canada
Deal found 3/30![Air Canada logo]()
$360
This Air Canada deal was found by Cheapflights users on 3/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/298:20 pm
ORD
- GCM
1 stop13h 40m
Air Canada
jue. 6/412:25 pm
GCM
- ORD
1 stop20h 40m
Air Canada
Deal found 3/31![Air Canada logo]()
$363
This Southwest deal was found by Cheapflights users on 3/29. 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.
mar. 4/286:00 am
MDW
- GCM
1 stop6h 10m
Southwest
mar. 5/51:05 pm
GCM
- MDW
2 stops18h 30m
Southwest
Deal found 3/29![Southwest logo]()
$507
This Southwest deal was found by Cheapflights users on 3/29. 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. 4/198:55 pm
MDW
- GCM
2 stops15h 15m
Southwest
mar. 4/281:05 pm
GCM
- MDW
2 stops8h 45m
Southwest
Deal found 3/29![Southwest logo]()
$528
This Southwest deal was found by Cheapflights users on 3/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/15:35 am
MDW
- GCM
1 stop6h 35m
Southwest
vie. 5/81:05 pm
GCM
- MDW
1 stop7h 35m
Southwest
Deal found 3/31![Southwest logo]()
$530
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
lun. 5/116:00 am
MDW
- GCM
2 stops15h 15m
Multiple Airlines
sáb. 5/161:45 pm
GCM
- MDW
1 stop20h 00m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$552
This Southwest deal was found by Cheapflights users on 4/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/235:35 am
MDW
- GCM
1 stop6h 35m
Southwest
mié. 4/291:05 pm
GCM
- MDW
1 stop8h 20m
Southwest
Deal found 4/1![Southwest logo]()
$575
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 abril 2, 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 abril 2, 2026.
This Southwest deal was found by Cheapflights users on 3/29. 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.
mié. 5/137:15 pm
ORD
- GCM
2 stops16h 55m
Southwest
mié. 5/201:05 pm
GCM
- ORD
1 stop8h 50m
Southwest
Deal found 3/29![Southwest logo]()
$497
This Delta deal was found by Cheapflights users on 4/1. 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.
dom. 5/36:38 pm
MDW
- GCM
2 stops17h 22m
Delta
vie. 5/291:19 pm
GCM
- MDW
2 stops19h 24m
Delta
Deal found 4/1![Delta logo]()
$600
This United Airlines deal was found by Cheapflights users on 3/27. 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.
vie. 4/248:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
lun. 4/271:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/27![United Airlines logo]()
$631
This Southwest deal was found by Cheapflights users on 3/29. 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.
mar. 4/286:00 am
MDW
- GCM
1 stop6h 10m
Southwest
mar. 5/51:05 pm
GCM
- MDW
1 stop6h 40m
Southwest
Deal found 3/29![Southwest logo]()
$516
This Southwest deal was found by Cheapflights users on 3/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/15:35 am
MDW
- GCM
1 stop6h 35m
Southwest
vie. 5/81:05 pm
GCM
- MDW
1 stop7h 35m
Southwest
Deal found 3/31![Southwest logo]()
$530
This Delta deal was found by Cheapflights users on 4/1. 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.
dom. 5/37:45 pm
ORD
- GCM
1 stop16h 15m
Delta
vie. 5/291:19 pm
GCM
- ORD
2 stops21h 10m
Delta
Deal found 4/1![Delta logo]()
$600
This United Airlines deal was found by Cheapflights users on 3/30. 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.
sáb. 5/99:29 am
ORD
- GCM
Nonstop4h 01m
United Airlines
sáb. 5/161:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/30![United Airlines logo]()
$631
This Southwest deal was found by Cheapflights users on 3/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/16:00 am
ORD
- GCM
1 stop6h 10m
Southwest
vie. 5/81:05 pm
GCM
- ORD
1 stop8h 50m
Southwest
Deal found 3/31![Southwest logo]()
$544
This Delta deal was found by Cheapflights users on 4/1. 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.
dom. 5/36:38 pm
MDW
- GCM
2 stops17h 22m
Delta
dom. 5/311:19 pm
GCM
- MDW
1 stop7h 50m
Delta
Deal found 4/1![Delta logo]()
$625
This United Airlines deal was found by Cheapflights users on 3/28. 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.
sáb. 5/305:30 am
ORD
- GCM
1 stop7h 00m
United Airlines
sáb. 6/61:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/28![United Airlines logo]()
$678
This Southwest deal was found by Cheapflights users on 4/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/236:00 am
ORD
- GCM
1 stop6h 10m
Southwest
mié. 4/291:05 pm
GCM
- ORD
1 stop8h 50m
Southwest
Deal found 4/1![Southwest logo]()
$565
This Delta deal was found by Cheapflights users on 4/1. 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.
dom. 5/37:43 pm
ORD
- GCM
2 stops16h 17m
Delta
dom. 5/311:19 pm
GCM
- ORD
1 stop8h 34m
Delta
Deal found 4/1![Delta logo]()
$625
This United Airlines deal was found by Cheapflights users on 3/27. 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.
dom. 4/268:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
mié. 4/291:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/27![United Airlines logo]()
$701
This Delta deal was found by Cheapflights users on 3/28. 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. 5/96:23 am
MDW
- GCM
1 stop5h 31m
Delta
sáb. 5/161:19 pm
GCM
- MDW
1 stop7h 50m
Delta
Deal found 3/28![Delta logo]()
$645
This Southwest deal was found by Cheapflights users on 3/29. 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.
jue. 5/145:35 am
MDW
- GCM
1 stop6h 35m
Southwest
jue. 5/211:05 pm
GCM
- MDW
1 stop7h 35m
Southwest
Deal found 3/29![Southwest logo]()
$603
This Delta deal was found by Cheapflights users on 3/28. 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. 8/226:00 am
MDW
- GCM
1 stop5h 41m
Delta
mié. 8/2612:56 pm
GCM
- MDW
1 stop8h 50m
Delta
Deal found 3/28![Delta logo]()
$646
This Delta deal was found by Cheapflights users on 3/31. 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.
vie. 5/296:23 am
MDW
- GCM
1 stop5h 31m
Delta
jue. 6/41:19 pm
GCM
- MDW
1 stop7h 50m
Delta
Deal found 3/31![Delta logo]()
$653
Last-minute flights from Chicago to Grand CaymanDiscover last-minute flight deals from Chicago to Grand Cayman. Data last updated abril 2, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Grand Cayman. Data last updated abril 2, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 3/30. 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.
sáb. 4/45:05 am
ORD
- GCM
1 stop7h 15m
Spirit Airlines
jue. 4/91:52 pm
GCM
- ORD
1 stop9h 25m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
mié. 4/86:10 pm
ORD
- GCM
1 stop18h 47m
Multiple Airlines
sáb. 4/111:15 pm
GCM
- ORD
1 stop6h 56m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$383
This Expedia deal was found by Cheapflights users on 3/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/125:05 am
ORD
- GCM
1 stop7h 52m
Multiple Airlines
jue. 4/1611:55 am
GCM
- ORD
1 stop25h 10m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 3/29. 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.
dom. 4/125:05 am
ORD
- GCM
1 stop7h 52m
Multiple Airlines
mié. 4/1511:30 am
GCM
- ORD
1 stop25h 35m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$386
This Southwest deal was found by Cheapflights users on 3/29. 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. 4/198:55 pm
MDW
- GCM
2 stops15h 15m
Southwest
mar. 4/281:05 pm
GCM
- MDW
2 stops8h 45m
Southwest
Deal found 3/29![Southwest logo]()
$528
This Southwest deal was found by Cheapflights users on 4/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/235:35 am
MDW
- GCM
1 stop6h 35m
Southwest
mié. 4/291:05 pm
GCM
- MDW
1 stop8h 20m
Southwest
Deal found 4/1![Southwest logo]()
$575
This Southwest deal was found by Cheapflights users on 3/29. 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.
mar. 4/286:00 am
MDW
- GCM
1 stop6h 10m
Southwest
mar. 5/51:05 pm
GCM
- MDW
2 stops18h 30m
Southwest
Deal found 3/29![Southwest logo]()
$507
This Southwest deal was found by Cheapflights users on 3/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/15:35 am
MDW
- GCM
1 stop6h 35m
Southwest
vie. 5/81:05 pm
GCM
- MDW
1 stop7h 35m
Southwest
Deal found 3/31![Southwest logo]()
$530
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
lun. 5/116:00 am
MDW
- GCM
2 stops15h 15m
Multiple Airlines
sáb. 5/161:45 pm
GCM
- MDW
1 stop20h 00m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$552
This Air Canada deal was found by Cheapflights users on 3/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/298:20 pm
ORD
- GCM
1 stop13h 40m
Air Canada
jue. 6/412:25 pm
GCM
- ORD
1 stop20h 40m
Air Canada
Deal found 3/31![Air Canada logo]()
$363
This Expedia deal was found by Cheapflights users on 3/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/293:50 pm
ORD
- GCM
1 stop18h 10m
Air Canada
lun. 6/112:25 pm
GCM
- ORD
2 stops21h 53m
Air Canada
Deal found 3/29![Air Canada logo]()
$366
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 abril 2, 2026.
Search for one-way flight options from Chicago to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated abril 2, 2026.
This Priceline deal was found by Cheapflights users on 3/28. 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.
sáb. 4/115:05 am
ORD
- GCM
1 stop7h 15m
Spirit Airlines
Deal found 3/28![Spirit Airlines logo]()
$94
This Air Canada deal was found by Cheapflights users on 4/1. 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.
mié. 6/38:20 pm
ORD
- GCM
1 stop15h 05m
Air Canada
Deal found 4/1![Air Canada logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
dom. 4/125:05 am
ORD
- GCM
1 stop7h 52m
Spirit Airlines
Deal found 3/28![Spirit Airlines logo]()
$123
This Air Canada deal was found by Cheapflights users on 3/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/21:55 pm
ORD
- GCM
2 stops45h 30m
Air Canada
Deal found 3/31![Air Canada logo]()
$128
This Air Canada deal was found by Cheapflights users on 4/1. 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.
mié. 4/294:15 pm
ORD
- GCM
1 stop18h 55m
Air Canada
Deal found 4/1![Air Canada logo]()
$136
This Air Canada deal was found by Cheapflights users on 4/1. 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.
dom. 5/318:35 pm
ORD
- GCM
1 stop14h 50m
Air Canada
Deal found 4/1![Air Canada logo]()
$138
This Expedia deal was found by Cheapflights users on 3/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/299:55 am
ORD
- GCM
1 stop24h 05m
Air Canada
Deal found 3/31![Air Canada logo]()
$141
This Expedia deal was found by Cheapflights users on 3/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/278:45 am
ORD
- GCM
2 stops26h 40m
Air Canada
Deal found 3/28![Air Canada logo]()
$144
This Air Canada deal was found by Cheapflights users on 3/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/275:35 pm
ORD
- GCM
1 stop17h 55m
Air Canada
Deal found 3/31![Air Canada logo]()
$148
This Air Canada deal was found by Cheapflights users on 3/29. 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.
dom. 4/267:13 am
ORD
- GCM
2 stops27h 02m
Air Canada
Deal found 3/29![Air Canada logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
sáb. 4/116:25 pm
MDW
- GCM
2 stops18h 32m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$197
This Southwest deal was found by Cheapflights users on 4/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 6/36:05 pm
MDW
- GCM
2 stops17h 45m
Southwest
Deal found 4/1![Southwest logo]()
$251
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 abril 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $345 (Expedia) |
One-way from | $94 (Priceline) |
Popular in | December |
Cheapest in | February |
Average price | $637 |
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 abril 2, 2026.
Use the filters below to find and compare flights from Chicago to Grand Cayman that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
mié. 5/13
7:15 pm-12:10 pm
2 stops16h 55m
George Town Owen Roberts Intl
mié. 5/20
1:05 pm-9:55 pm
1 stop8h 50m
$497
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
mar. 4/28
6:00 am-12:10 pm
1 stop6h 10m
George Town Owen Roberts Intl
mar. 5/5
1:05 pm-7:45 pm
1 stop6h 40m
$516
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
vie. 5/1
5:35 am-12:10 pm
1 stop6h 35m
George Town Owen Roberts Intl
vie. 5/8
1:05 pm-8:40 pm
1 stop7h 35m
$530
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
vie. 5/1
6:00 am-12:10 pm
1 stop6h 10m
George Town Owen Roberts Intl
vie. 5/8
1:05 pm-9:55 pm
1 stop8h 50m
$544
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
jue. 4/23
6:00 am-12:10 pm
1 stop6h 10m
George Town Owen Roberts Intl
mié. 4/29
1:05 pm-9:55 pm
1 stop8h 50m
$565
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
dom. 5/3
6:38 pm-12:00 pm
2 stops17h 22m
George Town Owen Roberts Intl
vie. 5/29
1:19 pm-8:43 am
2 stops19h 24m
$600
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
dom. 5/3
7:45 pm-12:00 pm
1 stop16h 15m
George Town Owen Roberts Intl
vie. 5/29
1:19 pm-10:29 am
2 stops21h 10m
$600
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
jue. 5/14
5:35 am-12:10 pm
1 stop6h 35m
George Town Owen Roberts Intl
jue. 5/21
1:05 pm-8:40 pm
1 stop7h 35m
$603
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
dom. 5/3
6:38 pm-12:00 pm
2 stops17h 22m
George Town Owen Roberts Intl
dom. 5/31
1:19 pm-9:09 pm
1 stop7h 50m
$625
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
dom. 5/3
7:43 pm-12:00 pm
2 stops16h 17m
George Town Owen Roberts Intl
dom. 5/31
1:19 pm-9:53 pm
1 stop8h 34m
$625
Showing 1-10 of 36 resultsSorted by cheapest first
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 abril 2, 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.
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 abril 2, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited 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.
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
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Chicago and Grand Cayman flights
Browse other Chicago and Grand Cayman flight options. Last updated on abril 2, 2026.
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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 abril 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$601 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$429 | Average$669 | FlexibilityNo cancel fee | On-time71% |