$102+ Cheap flights from O'Hare Intl (ORD) 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.
ORD — GCM
Apr 12 — Apr 191
Round-trip
1 adult, Economy
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Cheapest flights from O'Hare Intl to Grand CaymanExplore the most affordable flight options available from O'Hare Intl to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 13, 2026.
Explore the most affordable flight options available from O'Hare Intl to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 13, 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 Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/151:55 pm
ORD
- GCM
2 stops21h 00m
Air Canada
Thu 4/2311:55 am
GCM
- ORD
2 stops20h 05m
Air Canada
Deal found 3/13![Air Canada logo]()
$450
This Mytrip deal was found by Cheapflights users on 3/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/152:00 pm
ORD
- GCM
1 stop20h 55m
Multiple Airlines
Mon 4/204:45 pm
GCM
- ORD
2 stops24h 26m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$455
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 3/9. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/23:45 pm
ORD
- GCM
2 stops18h 25m
Air Canada
Thu 4/911:55 am
GCM
- ORD
2 stops20h 03m
Air Canada
Deal found 3/9![Air Canada logo]()
$465
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/266:04 pm
ORD
- GCM
2 stops17h 21m
Air Canada
Thu 4/911:55 am
GCM
- ORD
2 stops20h 03m
Air Canada
Deal found 3/9![Air Canada logo]()
$466
This Air Canada 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 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
Mon 4/2011:25 am
GCM
- ORD
1 stop21h 45m
Air Canada
Deal found 3/9![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
Best flights from O'Hare Intl to Grand CaymanDiscover carefully curated flight deals from O'Hare Intl to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 13, 2026.
Discover carefully curated flight deals from O'Hare Intl to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 13, 2026.
This Mytrip deal was found by Cheapflights users on 3/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/159:50 am
ORD
- GCM
1 stop25h 05m
Multiple Airlines
Mon 4/204:45 pm
GCM
- ORD
2 stops24h 26m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$455
This Southwest deal was found by Cheapflights users on 3/8. 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.
Sun 5/176:00 am
ORD
- GCM
1 stop5h 55m
Southwest
Fri 5/221:05 pm
GCM
- ORD
1 stop8h 50m
Southwest
Deal found 3/8![Southwest logo]()
$478
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:45 am
ORD
- GCM
1 stop8h 08m
JetBlue
Sat 5/302:15 pm
GCM
- ORD
1 stop8h 42m
JetBlue
Deal found 3/12![JetBlue logo]()
$573
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 3/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:30 am
ORD
- GCM
1 stop7h 00m
United Airlines
Sat 5/231:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/10![United Airlines logo]()
$615
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.
Tue 5/267:15 pm
ORD
- GCM
2 stops16h 55m
Southwest
Sun 5/3112:50 pm
GCM
- ORD
1 stop9h 05m
Southwest
Deal found 3/11![Southwest logo]()
$573
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 7/85:30 am
ORD
- GCM
1 stop7h 00m
United Airlines
Sat 7/184:45 pm
GCM
- ORD
1 stop8h 00m
United Airlines
Deal found 3/9![United Airlines logo]()
$636
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 FlightHub deal was found by Cheapflights users on 3/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/294:15 pm
ORD
- GCM
1 stop18h 00m
Multiple Airlines
Sat 4/410:35 am
GCM
- ORD
1 stop21h 30m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$658
This United Airlines deal was found by Cheapflights users on 3/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/158:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Mon 4/201:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/8![United Airlines logo]()
$647
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
Last-minute flights from O'Hare Intl to Grand CaymanDiscover last-minute flight deals from O'Hare Intl to Grand Cayman. Data last updated March 13, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Grand Cayman. Data last updated March 13, 2026 and is based on user searches.
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/266:04 pm
ORD
- GCM
2 stops17h 21m
Air Canada
Thu 4/911:55 am
GCM
- ORD
2 stops20h 03m
Air Canada
Deal found 3/9![Air Canada logo]()
$466
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/23:45 pm
ORD
- GCM
2 stops18h 25m
Air Canada
Thu 4/911:55 am
GCM
- ORD
2 stops20h 03m
Air Canada
Deal found 3/9![Air Canada logo]()
$465
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 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.
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 3/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/151:55 pm
ORD
- GCM
2 stops21h 00m
Air Canada
Thu 4/2311:55 am
GCM
- ORD
2 stops20h 05m
Air Canada
Deal found 3/13![Air Canada logo]()
$450
This Mytrip deal was found by Cheapflights users on 3/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/152:00 pm
ORD
- GCM
1 stop20h 55m
Multiple Airlines
Mon 4/204:45 pm
GCM
- ORD
2 stops24h 26m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$455
This Air Canada 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 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
Mon 4/2011:25 am
GCM
- ORD
1 stop21h 45m
Air Canada
Deal found 3/9![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 O'Hare Intl to Grand CaymanSearch for one-way flight options from O'Hare Intl to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated March 13, 2026.
Search for one-way flight options from O'Hare Intl to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated March 13, 2026.
This Priceline 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 Priceline 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 Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
ORD
- GCM
1 stop7h 52m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$107
This FlightHub 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 FlightHub 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
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$109
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 4/107:20 am
ORD
- GCM
1 stop29h 00m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 3/8. 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.
Wed 4/84:36 pm
ORD
- GCM
1 stop20h 21m
Spirit Airlines
Deal found 3/8![Spirit Airlines logo]()
$121
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.
Sun 4/128:40 am
ORD
- GCM
2 stops25h 35m
Air Canada
Deal found 3/13![Air Canada logo]()
$140
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/97:55 am
ORD
- GCM
1 stop26h 15m
Air Canada
Deal found 3/13![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 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 4/1011:25 am
ORD
- GCM
2 stops24h 55m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$144
Find flight deals from O'Hare Intl to Grand Cayman
Keep the following information in mind while searching for O'Hare Intl to Grand Cayman flight deals. Data was last updated March 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $449 (Mytrip) |
One-way from | $102 (Priceline) |
Popular in | December |
Cheapest in | February |
Average price | $685 |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl 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 13, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport 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
Wed 4/15
9:50 am-10:55 am
1 stop25h 05m
George Town Owen Roberts Intl
Mon 4/20
4:45 pm-5:11 pm
2 stops24h 26m
$455
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 5/17
6:00 am-11:55 am
1 stop5h 55m
George Town Owen Roberts Intl
Fri 5/22
1:05 pm-9:55 pm
1 stop8h 50m
$478
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 4/8
7:45 am-3:53 pm
1 stop8h 08m
George Town Owen Roberts Intl
Sat 5/30
2:15 pm-10:57 pm
1 stop8h 42m
$573
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 5/26
7:15 pm-12:10 pm
2 stops16h 55m
George Town Owen Roberts Intl
Sun 5/31
12:50 pm-9:55 pm
1 stop9h 05m
$573
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
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
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 5/16
5:30 am-12:30 pm
1 stop7h 00m
George Town Owen Roberts Intl
Sat 5/23
1:50 pm-6:13 pm
Nonstop4h 23m
$615
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 7/8
5:30 am-12:30 pm
1 stop7h 00m
George Town Owen Roberts Intl
Sat 7/18
4:45 pm-12:45 am
1 stop8h 00m
$636
Quickest round-trip
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 4/15
8:45 am-12:45 pm
Nonstop4h 00m
George Town Owen Roberts Intl
Mon 4/20
1:50 pm-6:13 pm
Nonstop4h 23m
$647
Showing 1-10 of 22 resultsSorted by cheapest first
Best time to book a flight from O'Hare Intl to Grand Cayman
Have a flexible travel schedule? Discover the best time to fly to Grand Cayman from O'Hare Intl with our price prediction graph.
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 O'Hare Intl Airport to Grand Cayman
ORD-zzLAW
ORD-GCM
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Grand Cayman?
Currently, December is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Grand Cayman (average of $322). Flying from Chicago O'Hare Intl Airport 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 ORD to LAW?
Find hourly flight availability from O'Hare Intl 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 13, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago O'Hare Intl Airport 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 March 13, 2026.
Get a feel of what it's like to fly with United Airlines and American Airlines from Chicago O'Hare Intl Airport to Grand Cayman by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.7
Overall
7.4
Food
6.6
Crew
8.1
Comfort
7.3
Entertainment
7.1
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Boarding
7.7
Overall
7.4
Food
6.6
Crew
8.1
Comfort
7.3
Entertainment
7.1
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Boarding
7.7
Overall
7.4
Food
6.6
Crew
8.1
Comfort
7.3
Entertainment
7.1
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl to Grand Cayman. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
Complete your trip to Grand Cayman by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from O'Hare Intl to Grand Cayman by cabin class
Find flights from O'Hare Intl to Grand Cayman, based on your preferred cabin class, be it economy, premium economy, business, or first class.
O'Hare Intl and Grand Cayman flights
Browse other O'Hare Intl and Grand Cayman flight options. Last updated on March 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from O'Hare Intl to Grand Cayman
Discover the top 2 airlines that operate flights from O'Hare Intl 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 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$590 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$438 | Average$668 | FlexibilityNo cancel fee | On-time71% |