$102+ 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
Apr 13 — Apr 201
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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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 March 14, 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 March 14, 2026.
This Mytrip deal was found by Cheapflights users on 3/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/412:45 pm
ORD
- GCM
3 stops24h 12m
Spirit Airlines
Thu 4/91:52 pm
GCM
- ORD
1 stop9h 25m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$449
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/55:05 am
ORD
- GCM
1 stop7h 52m
Multiple Airlines
Tue 4/1411:30 am
GCM
- ORD
1 stop7h 01m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$456
This FlightHub deal was found by Cheapflights users on 3/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/67:55 am
ORD
- GCM
1 stop27h 15m
Multiple Airlines
Mon 4/134:59 pm
GCM
- ORD
1 stop14h 42m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$457
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:05 am
ORD
- GCM
1 stop7h 15m
Multiple Airlines
Mon 5/254:45 pm
GCM
- ORD
2 stops39h 10m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$459
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 4/282:09 pm
ORD
- GCM
1 stop27h 51m
Multiple Airlines
Mon 5/44:45 pm
GCM
- ORD
2 stops39h 10m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$464
This Air Canada deal was found by Cheapflights users on 3/12. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/41:55 pm
ORD
- GCM
2 stops21h 00m
Air Canada
Thu 4/911:55 am
GCM
- ORD
1 stop7h 30m
Air Canada
Deal found 3/12![Air Canada logo]()
$466
This Air Canada deal was found by Cheapflights users on 3/10. 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.
Wed 4/154:15 pm
ORD
- GCM
1 stop18h 40m
Air Canada
Thu 4/2311:55 am
GCM
- ORD
1 stop21h 15m
Air Canada
Deal found 3/10![Air Canada logo]()
$467
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/55:05 am
ORD
- GCM
1 stop7h 52m
Multiple Airlines
Wed 4/88:00 am
GCM
- ORD
1 stop16h 22m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$468
This Air Canada deal was found by Cheapflights users on 3/10. 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.
Mon 4/136:40 pm
ORD
- GCM
1 stop16h 30m
Air Canada
Fri 4/1711:10 am
GCM
- ORD
1 stop8h 15m
Air Canada
Deal found 3/10![Air Canada logo]()
$469
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:10 pm
ORD
- GCM
1 stop18h 47m
Multiple Airlines
Wed 5/2711:30 am
GCM
- ORD
2 stops20h 25m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$471
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Wed 4/811:25 am
ORD
- GCM
2 stops25h 32m
Multiple Airlines
Fri 4/1711:25 am
GCM
- ORD
1 stop12h 33m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$472
This Priceline deal was found by Cheapflights users on 3/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/91:55 pm
ORD
- GCM
2 stops20h 15m
Multiple Airlines
Tue 4/143:05 pm
GCM
- ORD
2 stops30h 34m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$473
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 March 14, 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 March 14, 2026.
This Southwest deal was found by Cheapflights users on 3/9. 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.
Wed 4/86:50 pm
MDW
- GCM
2 stops17h 20m
Southwest
Fri 4/171:05 pm
GCM
- MDW
1 stop11h 00m
Southwest
Deal found 3/9![Southwest logo]()
$528
This Delta deal was found by Cheapflights users on 3/11. 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.
Tue 8/116:00 am
ORD
- GCM
1 stop5h 41m
Delta
Thu 11/51:55 pm
GCM
- ORD
1 stop8h 15m
Delta
Deal found 3/11![Delta logo]()
$611
This United Airlines deal was found by Cheapflights users on 3/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Mon 4/131:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/12![United Airlines logo]()
$667
This Southwest deal was found by Cheapflights users on 3/11. 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 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
Tue 4/141:05 pm
GCM
- MDW
1 stop8h 20m
Southwest
Deal found 3/11![Southwest logo]()
$559
This Southwest deal was found by Cheapflights users on 3/13. 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 4/46:20 pm
MDW
- GCM
2 stops17h 40m
Southwest
Thu 4/91:05 pm
GCM
- MDW
2 stops9h 40m
Southwest
Deal found 3/13![Southwest logo]()
$573
This Delta deal was found by Cheapflights users on 3/14. 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 8/266:00 am
ORD
- GCM
1 stop5h 41m
Delta
Sun 8/3012:56 pm
GCM
- ORD
1 stop8h 24m
Delta
Deal found 3/14![Delta logo]()
$656
This United Airlines deal was found by Cheapflights users on 3/9. 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.
Wed 4/88:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Fri 4/171:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/9![United Airlines logo]()
$667
This Southwest deal was found by Cheapflights users on 3/12. 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 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 5/281:05 pm
GCM
- MDW
1 stop11h 00m
Southwest
Deal found 3/12![Southwest logo]()
$582
This United Airlines deal was found by Cheapflights users on 3/13. 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 7/165:30 am
ORD
- GCM
1 stop7h 00m
United Airlines
Sat 7/251:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/13![United Airlines logo]()
$671
This Delta deal was found by Cheapflights users on 3/10. 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.
Thu 8/276:00 am
ORD
- GCM
1 stop5h 41m
Delta
Sun 8/3012:56 pm
GCM
- ORD
1 stop11h 01m
Delta
Deal found 3/10![Delta logo]()
$681
This Southwest deal was found by Cheapflights users on 3/12. 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 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
Mon 4/131:05 pm
GCM
- MDW
1 stop11h 00m
Southwest
Deal found 3/12![Southwest logo]()
$584
This United Airlines deal was found by Cheapflights users on 3/14. 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 8/19:29 am
ORD
- GCM
Nonstop4h 01m
United Airlines
Sat 8/84:45 pm
GCM
- ORD
1 stop8h 00m
United Airlines
Deal found 3/14![United Airlines logo]()
$677
This Southwest deal was found by Cheapflights users on 3/9. 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.
Sun 6/77:55 pm
ORD
- GCM
2 stops15h 55m
Southwest
Wed 6/1712:45 pm
GCM
- ORD
1 stop11h 10m
Southwest
Deal found 3/9![Southwest logo]()
$588
This United Airlines deal was found by Cheapflights users on 3/9. 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.
Fri 4/108:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Thu 4/161:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/9![United Airlines logo]()
$692
This Southwest deal was found by Cheapflights users on 3/10. 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.
Thu 4/26:00 am
MDW
- GCM
1 stop5h 25m
Southwest
Thu 4/91:05 pm
GCM
- MDW
1 stop11h 00m
Southwest
Deal found 3/10![Southwest logo]()
$597
This Southwest deal was found by Cheapflights users on 3/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/176:00 am
ORD
- GCM
1 stop5h 50m
Southwest
Wed 7/2212:45 pm
GCM
- ORD
1 stop11h 10m
Southwest
Deal found 3/12![Southwest logo]()
$603
This Southwest deal was found by Cheapflights users on 3/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
ORD
- GCM
1 stop6h 10m
Southwest
Sun 5/3112:50 pm
GCM
- ORD
1 stop9h 05m
Southwest
Deal found 3/11![Southwest logo]()
$603
This Southwest deal was found by Cheapflights users on 3/10. 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.
Fri 6/126:30 am
MDW
- GCM
1 stop5h 20m
Southwest
Wed 6/1712:45 pm
GCM
- MDW
2 stops10h 25m
Southwest
Deal found 3/10![Southwest logo]()
$628
This Southwest deal was found by Cheapflights users on 3/9. 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.
Fri 4/105:30 am
MDW
- GCM
2 stops6h 40m
Southwest
Thu 4/161:05 pm
GCM
- MDW
2 stops10h 50m
Southwest
Deal found 3/9![Southwest logo]()
$652
Last-minute flights from Chicago to Grand CaymanDiscover last-minute flight deals from Chicago to Grand Cayman. Data last updated March 14, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Grand Cayman. Data last updated March 14, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 3/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/412:45 pm
ORD
- GCM
3 stops24h 12m
Spirit Airlines
Thu 4/91:52 pm
GCM
- ORD
1 stop9h 25m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$449
This Air Canada deal was found by Cheapflights users on 3/12. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/41:55 pm
ORD
- GCM
2 stops21h 00m
Air Canada
Thu 4/911:55 am
GCM
- ORD
1 stop7h 30m
Air Canada
Deal found 3/12![Air Canada logo]()
$466
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/55:05 am
ORD
- GCM
1 stop7h 52m
Multiple Airlines
Tue 4/1411:30 am
GCM
- ORD
1 stop7h 01m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$456
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/55:05 am
ORD
- GCM
1 stop7h 52m
Multiple Airlines
Wed 4/88:00 am
GCM
- ORD
1 stop16h 22m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$468
This FlightHub deal was found by Cheapflights users on 3/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/67:55 am
ORD
- GCM
1 stop27h 15m
Multiple Airlines
Mon 4/134:59 pm
GCM
- ORD
1 stop14h 42m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$457
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:10 pm
ORD
- GCM
1 stop18h 47m
Multiple Airlines
Wed 5/2711:30 am
GCM
- ORD
2 stops20h 25m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$471
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Wed 4/811:25 am
ORD
- GCM
2 stops25h 32m
Multiple Airlines
Fri 4/1711:25 am
GCM
- ORD
1 stop12h 33m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$472
This Priceline deal was found by Cheapflights users on 3/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/91:55 pm
ORD
- GCM
2 stops20h 15m
Multiple Airlines
Tue 4/143:05 pm
GCM
- ORD
2 stops30h 34m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$473
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:05 am
ORD
- GCM
1 stop7h 15m
Multiple Airlines
Mon 5/254:45 pm
GCM
- ORD
2 stops39h 10m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$459
This Air Canada deal was found by Cheapflights users on 3/10. 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.
Mon 4/136:40 pm
ORD
- GCM
1 stop16h 30m
Air Canada
Fri 4/1711:10 am
GCM
- ORD
1 stop8h 15m
Air Canada
Deal found 3/10![Air Canada logo]()
$469
This Air Canada deal was found by Cheapflights users on 3/10. 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.
Wed 4/154:15 pm
ORD
- GCM
1 stop18h 40m
Air Canada
Thu 4/2311:55 am
GCM
- ORD
1 stop21h 15m
Air Canada
Deal found 3/10![Air Canada logo]()
$467
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 4/282:09 pm
ORD
- GCM
1 stop27h 51m
Multiple Airlines
Mon 5/44:45 pm
GCM
- ORD
2 stops39h 10m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$464
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 March 14, 2026.
Search for one-way flight options from Chicago to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated March 14, 2026.
This FlightHub deal was found by Cheapflights users on 3/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:05 am
ORD
- GCM
1 stop7h 15m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$102
This FlightHub deal was found by Cheapflights users on 3/14. 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 4/57:17 am
ORD
- GCM
1 stop5h 40m
Spirit Airlines
Deal found 3/14![Spirit Airlines logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 4/106:10 pm
ORD
- GCM
1 stop18h 10m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
Wed 4/88:10 am
ORD
- GCM
1 stop28h 47m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/84:36 pm
ORD
- GCM
1 stop20h 21m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$127
This Expedia deal was found by Cheapflights users on 3/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/298:20 pm
ORD
- GCM
1 stop13h 55m
Air Canada
Deal found 3/12![Air Canada logo]()
$136
This Expedia deal was found by Cheapflights users on 3/13. 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.
Mon 4/138:40 am
ORD
- GCM
2 stops26h 30m
Air Canada
Deal found 3/13![Air Canada logo]()
$140
This Air Canada deal was found by Cheapflights users on 3/12. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/99:20 pm
ORD
- GCM
1 stop12h 50m
Air Canada
Deal found 3/12![Air Canada logo]()
$141
This Priceline deal was found by Cheapflights users on 3/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:05 am
ORD
- GCM
1 stop7h 52m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$142
This Trip.com deal was found by Cheapflights users on 3/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:30 am
MDW
- GCM
1 stop15h 05m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/39:20 am
MDW
- GCM
2 stops51h 37m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/286:55 am
MDW
- GCM
2 stops30h 02m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$218
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 March 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $449 (Mytrip) |
One-way from | $102 (FlightHub) |
Popular in | December |
Cheapest in | February |
Average price | $685 |
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 March 14, 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
Wed 4/8
6:50 pm-12:10 pm
2 stops17h 20m
George Town Owen Roberts Intl
Fri 4/17
1:05 pm-12:05 am
1 stop11h 00m
$528
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Thu 4/9
9:15 pm-12:10 pm
2 stops14h 55m
George Town Owen Roberts Intl
Tue 4/14
1:05 pm-9:25 pm
1 stop8h 20m
$559
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Sat 4/4
6:20 pm-12:00 pm
2 stops17h 40m
George Town Owen Roberts Intl
Thu 4/9
1:05 pm-10:45 pm
2 stops9h 40m
$573
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Thu 4/9
9:15 pm-12:10 pm
2 stops14h 55m
George Town Owen Roberts Intl
Thu 5/28
1:05 pm-12:05 am
1 stop11h 00m
$582
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Thu 4/9
9:15 pm-12:10 pm
2 stops14h 55m
George Town Owen Roberts Intl
Mon 4/13
1:05 pm-12:05 am
1 stop11h 00m
$584
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 6/7
7:55 pm-11:50 am
2 stops15h 55m
George Town Owen Roberts Intl
Wed 6/17
12:45 pm-11:55 pm
1 stop11h 10m
$588
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Thu 4/2
6:00 am-11:25 am
1 stop5h 25m
George Town Owen Roberts Intl
Thu 4/9
1:05 pm-12:05 am
1 stop11h 00m
$597
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Fri 7/17
6:00 am-11:50 am
1 stop5h 50m
George Town Owen Roberts Intl
Wed 7/22
12:45 pm-11:55 pm
1 stop11h 10m
$603
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Thu 5/28
6:00 am-12:10 pm
1 stop6h 10m
George Town Owen Roberts Intl
Sun 5/31
12:50 pm-9:55 pm
1 stop9h 05m
$603
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 8/11
6:00 am-11:41 am
1 stop5h 41m
George Town Owen Roberts Intl
Thu 11/5
1:55 pm-9:10 pm
1 stop8h 15m
$611
Showing 1-10 of 40 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.
MDW-GCM
ORD-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
MDW-GCM
ORD-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 March 14, 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 March 14, 2026.
The most flights from CHI to zzLAW are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 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 March 14, 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.
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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 March 14, 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 March 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$593 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$429 | Average$663 | FlexibilityNo cancel fee | On-time71% |