$170+ 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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Aug 11 — Aug 181
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 July 12, 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 July 12, 2026.
This Southwest deal was found by Cheapflights users on 7/10. 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 11/38:50 pm
MDW
- GCM
2 stops14h 45m
Southwest
Thu 11/121:30 pm
GCM
- MDW
1 stop6h 25m
Southwest
Deal found 7/10![Southwest logo]()
$425
This Air Canada deal was found by Cheapflights users on 7/11. 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.
Fri 9/115:35 pm
ORD
- GCM
1 stop16h 10m
Air Canada
Thu 9/1712:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 7/11![Air Canada logo]()
$429
This Travelocity deal was found by Cheapflights users on 7/10. 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.
Sat 10/33:40 pm
ORD
- GCM
2 stops43h 50m
Air Canada
Sat 10/1012:25 pm
GCM
- ORD
1 stop24h 58m
Air Canada
Deal found 7/10![Air Canada logo]()
$461
This Southwest deal was found by Cheapflights users on 7/8. 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 8/225:00 am
MDW
- GCM
1 stop7h 05m
Southwest
Sat 8/291:00 pm
GCM
- MDW
2 stops16h 40m
Southwest
Deal found 7/8![Southwest logo]()
$463
This Orbitz deal was found by Cheapflights users on 7/11. 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.
Thu 10/156:21 pm
ORD
- GCM
2 stops41h 09m
Air Canada
Mon 10/1912:25 pm
GCM
- ORD
1 stop28h 33m
Air Canada
Deal found 7/11![Air Canada logo]()
$469
This Mytrip deal was found by Cheapflights users on 7/11. 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 10/248:40 pm
ORD
- GCM
1 stop14h 30m
Air Canada
Sat 10/3112:10 pm
GCM
- ORD
1 stop8h 03m
Air Canada
Deal found 7/11![Air Canada logo]()
$472
This Expedia deal was found by Cheapflights users on 7/7. 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.
Wed 9/233:45 pm
ORD
- GCM
1 stop19h 40m
Air Canada
Sat 9/2610:40 am
GCM
- ORD
1 stop26h 43m
Air Canada
Deal found 7/7![Air Canada logo]()
$481
This Southwest deal was found by Cheapflights users on 7/7. 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 11/25:10 am
MDW
- GCM
1 stop6h 25m
Southwest
Thu 11/121:30 pm
GCM
- MDW
1 stop8h 05m
Southwest
Deal found 7/7![Southwest logo]()
$482
This Justfly.com deal was found by Cheapflights users on 7/9. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/143:45 pm
ORD
- GCM
1 stop19h 45m
Air Canada
Mon 10/1912:25 pm
GCM
- ORD
1 stop9h 41m
Air Canada
Deal found 7/9![Air Canada logo]()
$490
This Southwest deal was found by Cheapflights users on 7/7. 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.
Wed 11/44:15 pm
MDW
- GCM
2 stops19h 20m
Southwest
Thu 11/121:30 pm
GCM
- MDW
2 stops10h 35m
Southwest
Deal found 7/7![Southwest logo]()
$504
This Southwest deal was found by Cheapflights users on 7/7. 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 11/55:10 am
MDW
- GCM
1 stop6h 25m
Southwest
Thu 11/121:30 pm
GCM
- MDW
1 stop8h 05m
Southwest
Deal found 7/7![Southwest logo]()
$510
This Southwest deal was found by Cheapflights users on 7/8. 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 11/35:15 am
MDW
- GCM
1 stop6h 20m
Southwest
Fri 11/131:30 pm
GCM
- MDW
1 stop6h 25m
Southwest
Deal found 7/8![Southwest logo]()
$513
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 July 12, 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 July 12, 2026.
This Southwest deal was found by Cheapflights users on 7/10. 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 11/38:50 pm
MDW
- GCM
2 stops14h 45m
Southwest
Thu 11/121:30 pm
GCM
- MDW
1 stop6h 25m
Southwest
Deal found 7/10![Southwest logo]()
$425
This Mytrip deal was found by Cheapflights users on 7/11. 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 10/248:40 pm
ORD
- GCM
1 stop14h 30m
Air Canada
Sat 10/3112:10 pm
GCM
- ORD
1 stop8h 03m
Air Canada
Deal found 7/11![Air Canada logo]()
$472
This Delta deal was found by Cheapflights users on 7/11. 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 1/36:00 am
MDW
- GCM
1 stop5h 40m
Delta
Wed 1/132:05 pm
GCM
- MDW
1 stop9h 05m
Delta
Deal found 7/11![Delta logo]()
$611
This United Airlines deal was found by Cheapflights users on 7/9. 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 12/218:42 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Fri 12/252:50 pm
GCM
- ORD
Nonstop4h 14m
United Airlines
Deal found 7/9![United Airlines logo]()
$622
This Southwest deal was found by Cheapflights users on 7/7. 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 11/28:25 pm
MDW
- GCM
2 stops15h 10m
Southwest
Thu 11/121:30 pm
GCM
- MDW
2 stops7h 50m
Southwest
Deal found 7/7![Southwest logo]()
$455
This Southwest deal was found by Cheapflights users on 7/10. 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 11/38:50 pm
MDW
- GCM
2 stops14h 45m
Southwest
Fri 11/131:30 pm
GCM
- MDW
2 stops10h 35m
Southwest
Deal found 7/10![Southwest logo]()
$487
This Delta deal was found by Cheapflights users on 7/8. 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 11/115:30 am
ORD
- GCM
1 stop5h 55m
Delta
Fri 11/201:50 pm
GCM
- ORD
2 stops19h 14m
Delta
Deal found 7/8![Delta logo]()
$616
This United Airlines deal was found by Cheapflights users on 7/7. 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 11/37:40 am
ORD
- GCM
1 stop7h 50m
United Airlines
Sat 11/142:50 pm
GCM
- ORD
Nonstop4h 14m
United Airlines
Deal found 7/7![United Airlines logo]()
$636
This Delta deal was found by Cheapflights users on 7/9. 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 11/175:30 am
ORD
- GCM
1 stop5h 55m
Delta
Mon 11/231:50 pm
GCM
- ORD
1 stop8h 20m
Delta
Deal found 7/9![Delta logo]()
$646
This United Airlines deal was found by Cheapflights users on 7/7. 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 11/56:00 am
ORD
- GCM
1 stop9h 30m
United Airlines
Thu 11/125:45 pm
GCM
- ORD
1 stop16h 21m
United Airlines
Deal found 7/7![United Airlines logo]()
$646
This Delta deal was found by Cheapflights users on 7/8. 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 11/157:55 pm
ORD
- GCM
1 stop15h 30m
Delta
Mon 11/231:50 pm
GCM
- ORD
1 stop8h 20m
Delta
Deal found 7/8![Delta logo]()
$646
This Delta deal was found by Cheapflights users on 7/9. 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 11/115:30 am
ORD
- GCM
1 stop5h 55m
Delta
Mon 11/231:50 pm
GCM
- ORD
1 stop8h 20m
Delta
Deal found 7/9![Delta logo]()
$646
This Delta deal was found by Cheapflights users on 7/8. 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 11/115:30 am
ORD
- GCM
1 stop5h 55m
Delta
Sun 11/221:50 pm
GCM
- ORD
1 stop11h 00m
Delta
Deal found 7/8![Delta logo]()
$646
This Delta deal was found by Cheapflights users on 7/7. 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 9/145:30 am
ORD
- GCM
1 stop6h 10m
Delta
Fri 9/181:00 pm
GCM
- ORD
1 stop10h 59m
Delta
Deal found 7/7![Delta logo]()
$661
This Delta deal was found by Cheapflights users on 7/7. 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 8/216:05 am
MDW
- GCM
1 stop5h 34m
Delta
Fri 8/281:04 pm
GCM
- MDW
1 stop9h 32m
Delta
Deal found 7/7![Delta logo]()
$681
This Delta deal was found by Cheapflights users on 7/12. 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 8/266:05 am
MDW
- GCM
1 stop5h 34m
Delta
Wed 9/21:04 pm
GCM
- MDW
1 stop9h 32m
Delta
Deal found 7/12![Delta logo]()
$681
This Delta deal was found by Cheapflights users on 7/10. 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 8/286:05 am
MDW
- GCM
1 stop5h 34m
Delta
Mon 8/311:04 pm
GCM
- MDW
1 stop9h 32m
Delta
Deal found 7/10![Delta logo]()
$681
This Delta deal was found by Cheapflights users on 7/9. 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 9/56:05 am
MDW
- GCM
1 stop5h 34m
Delta
Sat 9/121:05 pm
GCM
- MDW
1 stop9h 40m
Delta
Deal found 7/9![Delta logo]()
$681
This Delta deal was found by Cheapflights users on 7/8. 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 8/86:30 pm
ORD
- GCM
1 stop17h 09m
Delta
Thu 8/201:04 pm
GCM
- ORD
1 stop7h 51m
Delta
Deal found 7/8![Delta logo]()
$681
This Delta deal was found by Cheapflights users on 7/9. 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 11/135:30 am
ORD
- GCM
1 stop5h 55m
Delta
Mon 11/231:50 pm
GCM
- ORD
1 stop8h 20m
Delta
Deal found 7/9![Delta logo]()
$681
Last-minute flights from Chicago to Grand CaymanDiscover last-minute flight deals from Chicago to Grand Cayman. Data last updated July 12, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Grand Cayman. Data last updated July 12, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:30 am
ORD
- GCM
1 stop6h 09m
Delta
Thu 8/201:04 pm
GCM
- ORD
1 stop7h 51m
Delta
Deal found 7/8![Delta logo]()
$681
This American Airlines deal was found by Cheapflights users on 7/7. 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 8/206:59 am
ORD
- GCM
1 stop6h 11m
American Airlines
Thu 8/272:10 pm
GCM
- ORD
1 stop10h 25m
American Airlines
Deal found 7/7![American Airlines logo]()
$671
This Trip.com deal was found by Cheapflights users on 7/7. 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.
Fri 8/216:05 am
MDW
- GCM
2 stops15h 10m
Multiple Airlines
Fri 8/287:00 am
GCM
- MDW
2 stops15h 47m
Multiple Airlines
Deal found 7/7![Multiple Airlines logo]()
$616
This Southwest deal was found by Cheapflights users on 7/8. 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 8/225:00 am
MDW
- GCM
1 stop7h 05m
Southwest
Sat 8/291:00 pm
GCM
- MDW
2 stops16h 40m
Southwest
Deal found 7/8![Southwest logo]()
$463
This Mytrip deal was found by Cheapflights users on 7/7. 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 8/239:50 am
ORD
- GCM
1 stop25h 35m
Air Canada
Mon 8/3112:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 7/7![Air Canada logo]()
$659
This Delta deal was found by Cheapflights users on 7/9. 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 8/236:05 am
MDW
- GCM
1 stop5h 34m
Delta
Sun 8/301:04 pm
GCM
- MDW
1 stop9h 32m
Delta
Deal found 7/9![Delta logo]()
$681
This American Airlines deal was found by Cheapflights users on 7/10. 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 8/245:00 am
ORD
- GCM
1 stop8h 10m
American Airlines
Mon 8/312:10 pm
GCM
- ORD
1 stop10h 25m
American Airlines
Deal found 7/10![American Airlines logo]()
$673
This American Airlines deal was found by Cheapflights users on 7/12. 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 8/268:53 pm
ORD
- GCM
2 stops14h 07m
American Airlines
Wed 9/212:30 pm
GCM
- ORD
1 stop11h 22m
American Airlines
Deal found 7/12![American Airlines logo]()
$687
This Trip.com deal was found by Cheapflights users on 7/8. 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 8/276:05 am
MDW
- GCM
2 stops15h 10m
Multiple Airlines
Sun 8/307:00 am
GCM
- MDW
2 stops15h 47m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$581
This Trip.com deal was found by Cheapflights users on 7/8. 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 8/277:05 am
ORD
- GCM
2 stops14h 10m
Multiple Airlines
Sun 8/307:00 am
GCM
- ORD
2 stops24h 29m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$603
This Orbitz deal was found by Cheapflights users on 7/10. 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.
Fri 8/283:45 pm
ORD
- GCM
1 stop18h 00m
Air Canada
Mon 8/3112:25 pm
GCM
- ORD
1 stop28h 32m
Air Canada
Deal found 7/10![Air Canada logo]()
$553
This Kiwi.com deal was found by Cheapflights users on 7/10. 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 8/283:15 pm
MDW
- GCM
1 stop21h 30m
Multiple Airlines
Mon 8/317:00 am
GCM
- MDW
2 stops15h 47m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$711
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 July 12, 2026.
Search for one-way flight options from Chicago to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated July 12, 2026.
This Air Canada deal was found by Cheapflights users on 7/11. 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.
Sun 9/138:50 am
ORD
- GCM
1 stop26h 35m
Air Canada
Deal found 7/11![Air Canada logo]()
$170
This Air Canada deal was found by Cheapflights users on 7/11. 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 9/911:05 am
ORD
- GCM
2 stops24h 20m
Air Canada
Deal found 7/11![Air Canada logo]()
$173
This Air Canada deal was found by Cheapflights users on 7/11. 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 10/78:40 pm
ORD
- GCM
1 stop14h 50m
Air Canada
Deal found 7/11![Air Canada logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 7/10. 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 9/108:00 am
ORD
- GCM
2 stops27h 35m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$192
This Travelocity deal was found by Cheapflights users on 7/10. 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 9/83:40 pm
ORD
- GCM
2 stops43h 45m
Air Canada
Deal found 7/10![Air Canada logo]()
$194
This Air Canada deal was found by Cheapflights users on 7/8. 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.
Sun 10/47:09 am
ORD
- GCM
1 stop28h 21m
Air Canada
Deal found 7/8![Air Canada logo]()
$196
This Air Canada deal was found by Cheapflights users on 7/8. 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 9/102:01 pm
ORD
- GCM
2 stops43h 44m
Air Canada
Deal found 7/8![Air Canada logo]()
$199
This Air Canada deal was found by Cheapflights users on 7/10. 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 10/314:30 pm
ORD
- GCM
1 stop19h 40m
Air Canada
Deal found 7/10![Air Canada logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 9/36:00 am
ORD
- GCM
2 stops39h 15m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 8/49:34 pm
ORD
- GCM
2 stops38h 01m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 7/10. 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 8/119:34 pm
ORD
- GCM
2 stops38h 01m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$207
This Southwest deal was found by Cheapflights users on 7/9. 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 10/317:10 pm
MDW
- GCM
2 stops17h 25m
Southwest
Deal found 7/9![Southwest logo]()
$220
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 July 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $425 (Southwest) |
One-way from | $170 (Air Canada) |
Popular in | July |
Cheapest in | October |
Average price | $853 |
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 July 12, 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
MDW - GCM
MDWGCM
Chicago Midway
Tue 11/3
8:50 pm-12:35 pm
2 stops14h 45m
George Town Owen Roberts Intl
Thu 11/12
1:30 pm-6:55 pm
1 stop6h 25m
$425
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Mon 11/2
8:25 pm-12:35 pm
2 stops15h 10m
George Town Owen Roberts Intl
Thu 11/12
1:30 pm-8:20 pm
2 stops7h 50m
$455
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 10/24
8:40 pm-11:10 am
1 stop14h 30m
George Town Owen Roberts Intl
Sat 10/31
12:10 pm-8:13 pm
1 stop8h 03m
$472
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Tue 11/3
8:50 pm-12:35 pm
2 stops14h 45m
George Town Owen Roberts Intl
Fri 11/13
1:30 pm-11:05 pm
2 stops10h 35m
$487
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Sun 1/3
6:00 am-12:40 pm
1 stop5h 40m
George Town Owen Roberts Intl
Wed 1/13
2:05 pm-10:10 pm
1 stop9h 05m
$611
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 11/11
5:30 am-12:25 pm
1 stop5h 55m
George Town Owen Roberts Intl
Fri 11/20
1:50 pm-8:04 am
2 stops19h 14m
$616
Quickest round-trip
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Mon 12/21
8:42 am-1:42 pm
Nonstop4h 00m
George Town Owen Roberts Intl
Fri 12/25
2:50 pm-6:04 pm
Nonstop4h 14m
$622
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 11/3
7:40 am-4:30 pm
1 stop7h 50m
George Town Owen Roberts Intl
Sat 11/14
2:50 pm-6:04 pm
Nonstop4h 14m
$636
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 11/17
5:30 am-12:25 pm
1 stop5h 55m
George Town Owen Roberts Intl
Mon 11/23
1:50 pm-9:10 pm
1 stop8h 20m
$646
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Thu 11/5
6:00 am-4:30 pm
1 stop9h 30m
George Town Owen Roberts Intl
Thu 11/12
5:45 pm-9:06 am
1 stop16h 21m
$646
Showing 1-10 of 35 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 $172). Flying from Chicago to Grand Cayman in September is currently the most expensive (average of $621). 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 July 12, 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 July 12, 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.
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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
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Chicago and Grand Cayman flights
Browse other Chicago and Grand Cayman flight options. Last updated on July 12, 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 July 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$611 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$438 | Average$683 | FlexibilityNo cancel fee | On-time71% |