$107+ Cheap flights from O'Hare Intl (ORD) to the Cayman Islands
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 4/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Apr 10 — Apr 171
Round-trip
1 adult, Economy
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Cheapest flights from O'Hare Intl to Cayman IslandsExplore the most affordable flight options available from O'Hare Intl to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 11, 2026.
Explore the most affordable flight options available from O'Hare Intl to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 11, 2026.
This Priceline deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/197:17 am
ORD
- GCM
1 stop5h 40m
Spirit Airlines
Sun 3/221:52 pm
GCM
- ORD
1 stop9h 25m
Spirit Airlines
Deal found 3/6![Spirit Airlines logo]()
$447
This FlightHub deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 3/145:05 am
ORD
- GCM
1 stop7h 15m
Spirit Airlines
Thu 3/191:52 pm
GCM
- ORD
1 stop9h 25m
Spirit Airlines
Deal found 3/6![Spirit Airlines logo]()
$453
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/64:51 pm
ORD
- GCM
1 stop23h 14m
Multiple Airlines
Sun 4/121:52 pm
GCM
- ORD
1 stop21h 25m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$454
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 Mytrip deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/125:05 am
ORD
- GCM
1 stop7h 52m
Multiple Airlines
Tue 3/1711:30 am
GCM
- ORD
1 stop7h 01m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$456
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:45 am
ORD
- GCM
1 stop9h 08m
JetBlue
Mon 4/134:59 pm
GCM
- ORD
1 stop14h 42m
JetBlue
Deal found 3/8![JetBlue logo]()
$460
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 4/14:51 pm
ORD
- GCM
1 stop18h 44m
Multiple Airlines
Mon 4/134:45 pm
GCM
- ORD
1 stop17h 05m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$463
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.
Thu 5/73:52 pm
ORD
- GCM
1 stop19h 43m
Multiple Airlines
Mon 5/114:45 pm
GCM
- ORD
2 stops24h 26m
Multiple Airlines
Deal found 3/9![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 Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/98:40 pm
ORD
- CYB
2 stops18h 45m
Multiple Airlines
Mon 3/168:30 am
CYB
- ORD
2 stops11h 15m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$703
Best flights from O'Hare Intl to Cayman IslandsDiscover carefully curated flight deals from O'Hare Intl to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 11, 2026.
Discover carefully curated flight deals from O'Hare Intl to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 11, 2026.
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 Mytrip deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/212:50 pm
ORD
- GCM
3 stops24h 10m
Multiple Airlines
Tue 4/712:30 pm
GCM
- ORD
2 stops22h 23m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$559
This Delta deal was found by Cheapflights users on 3/7. 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.
Sun 9/66:00 am
ORD
- GCM
1 stop5h 41m
Delta
Sun 9/1312:55 pm
GCM
- ORD
1 stop8h 25m
Delta
Deal found 3/7![Delta logo]()
$616
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.
Sun 6/78:02 pm
ORD
- GCM
1 stop16h 28m
United Airlines
Sat 6/131:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/9![United Airlines logo]()
$626
This Southwest deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 5/36:00 am
ORD
- GCM
1 stop5h 55m
Southwest
Thu 5/71:05 pm
GCM
- ORD
1 stop8h 50m
Southwest
Deal found 3/6![Southwest logo]()
$517
This United Airlines deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/28:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Tue 4/71:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/5![United Airlines 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.
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 3/7. 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.
Wed 4/228:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Wed 4/291:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/7![United Airlines logo]()
$637
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.
Tue 4/78:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Tue 4/141:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/8![United Airlines logo]()
$647
This United Airlines deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/185:48 am
ORD
- GCM
1 stop6h 42m
United Airlines
Sat 4/251:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/5![United Airlines logo]()
$659
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/89:20 pm
ORD
- CYB
2 stops18h 05m
Multiple Airlines
Sat 4/116:20 pm
CYB
- ORD
2 stops25h 05m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$1,257
Last-minute flights from O'Hare Intl to Cayman IslandsDiscover last-minute flight deals from O'Hare Intl to Cayman Islands. Data last updated March 11, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Cayman Islands. Data last updated March 11, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/125:05 am
ORD
- GCM
1 stop7h 52m
Multiple Airlines
Tue 3/1711:30 am
GCM
- ORD
1 stop7h 01m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$456
This FlightHub deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 3/145:05 am
ORD
- GCM
1 stop7h 15m
Spirit Airlines
Thu 3/191:52 pm
GCM
- ORD
1 stop9h 25m
Spirit Airlines
Deal found 3/6![Spirit Airlines logo]()
$453
This Priceline deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/197:17 am
ORD
- GCM
1 stop5h 40m
Spirit Airlines
Sun 3/221:52 pm
GCM
- ORD
1 stop9h 25m
Spirit Airlines
Deal found 3/6![Spirit Airlines logo]()
$447
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 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 4/14:51 pm
ORD
- GCM
1 stop18h 44m
Multiple Airlines
Mon 4/134:45 pm
GCM
- ORD
1 stop17h 05m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$463
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 Kiwi.com deal was found by Cheapflights users on 3/7. 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 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 3/7![Multiple Airlines logo]()
$468
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/64:51 pm
ORD
- GCM
1 stop23h 14m
Multiple Airlines
Sun 4/121:52 pm
GCM
- ORD
1 stop21h 25m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$454
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:45 am
ORD
- GCM
1 stop9h 08m
JetBlue
Mon 4/134:59 pm
GCM
- ORD
1 stop14h 42m
JetBlue
Deal found 3/8![JetBlue logo]()
$460
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 4/104:51 pm
ORD
- CYB
1 stop20h 29m
Multiple Airlines
Tue 4/143:55 pm
CYB
- ORD
2 stops28h 02m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$836
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
One-way flights from O'Hare Intl to Cayman IslandsSearch for one-way flight options from O'Hare Intl to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated March 11, 2026.
Search for one-way flight options from O'Hare Intl to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated March 11, 2026.
This Priceline deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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.
Sun 4/57:17 am
ORD
- GCM
1 stop5h 40m
Spirit Airlines
Deal found 3/6![Spirit Airlines logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/36:10 pm
ORD
- GCM
1 stop18h 10m
Spirit Airlines
Deal found 3/6![Spirit 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 Gotogate deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/25:05 am
ORD
- GCM
1 stop7h 52m
Spirit Airlines
Deal found 3/6![Spirit Airlines logo]()
$130
This Air Canada deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 5/32:15 pm
ORD
- GCM
1 stop21h 10m
Air Canada
Deal found 3/5![Air Canada logo]()
$140
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 3/6. Clicking the “Pick Dates” 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 4/412:45 pm
ORD
- GCM
2 stops24h 12m
Spirit Airlines
Deal found 3/6![Spirit Airlines logo]()
$144
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:21 pm
ORD
- GCM
2 stops39h 54m
Air Canada
Deal found 3/8![Air Canada logo]()
$145
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/308:20 pm
ORD
- GCM
1 stop14h 50m
Air Canada
Deal found 3/8![Air Canada logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/74:51 pm
ORD
- GCM
1 stop23h 14m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$152
Find flight deals from O'Hare Intl to Cayman Islands
Keep the following information in mind while searching for O'Hare Intl to Cayman Islands flight deals. Data was last updated March 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $450 (Mytrip) |
One-way from | $107 (Priceline) |
Popular in | December |
Cheapest in | February |
Average price | $685 |
Good round-trip deal | $550 or less |
Good one-way deal | $276 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl to Cayman Islands 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 11, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to the Cayman Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
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
Sun 5/3
6:00 am-11:55 am
1 stop5h 55m
George Town Owen Roberts Intl
Thu 5/7
1:05 pm-9:55 pm
1 stop8h 50m
$517
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Thu 4/2
12:50 pm-1:00 pm
3 stops24h 10m
George Town Owen Roberts Intl
Tue 4/7
12:30 pm-10:53 am
2 stops22h 23m
$559
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
Sun 9/6
6:00 am-11:41 am
1 stop5h 41m
George Town Owen Roberts Intl
Sun 9/13
12:55 pm-9:20 pm
1 stop8h 25m
$616
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 6/7
8:02 pm-12:30 pm
1 stop16h 28m
George Town Owen Roberts Intl
Sat 6/13
1:50 pm-6:13 pm
Nonstop4h 23m
$626
Quickest round-trip
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Thu 4/2
8:45 am-12:45 pm
Nonstop4h 00m
George Town Owen Roberts Intl
Tue 4/7
1:50 pm-6:13 pm
Nonstop4h 23m
$628
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 4/22
8:45 am-12:45 pm
Nonstop4h 00m
George Town Owen Roberts Intl
Wed 4/29
1:50 pm-6:13 pm
Nonstop4h 23m
$637
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 4/7
8:45 am-12:45 pm
Nonstop4h 00m
George Town Owen Roberts Intl
Tue 4/14
1:50 pm-6:13 pm
Nonstop4h 23m
$647
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 4/18
5:48 am-12:30 pm
1 stop6h 42m
George Town Owen Roberts Intl
Sat 4/25
1:50 pm-6:13 pm
Nonstop4h 23m
$659
Showing 1-10 of 20 resultsSorted by cheapest first
Best time to book a flight from O'Hare Intl to Cayman Islands
Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from O'Hare Intl with our price prediction graph.
ORD-GCM
ORD-CYB
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 the Cayman Islands
ORD-KY0
ORD-GCM
ORD-CYB
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Cayman Islands?
Currently, December is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Cayman Islands (average of $322). Flying from Chicago O'Hare Intl Airport to Cayman Islands 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 KY?
Find hourly flight availability from O'Hare Intl to Cayman Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 11, 2026.
When flying from Chicago O'Hare Intl Airport to Cayman Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Reviews of airlines servicing Cayman Islands
Get insights into the airlines that provide service to Cayman Islands. 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 Cayman Islands. Reviews last updated March 11, 2026.
Get a feel of what it's like to fly with United Airlines and American Airlines from Chicago O'Hare Intl Airport to the Cayman Islands by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.1
Crew
8.1
Comfort
7.3
Food
6.6
Boarding
7.7
Overall
7.4
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Crew
8.1
Comfort
7.3
Food
6.6
Boarding
7.7
Overall
7.4
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Crew
8.1
Comfort
7.3
Food
6.6
Boarding
7.7
Overall
7.4
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 Cayman Islands. 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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Alternative routes for O'Hare Intl to Cayman Islands
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Complete your trip
Complete your trip to Cayman Islands by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from O'Hare Intl to Cayman Islands by cabin class
Find flights from O'Hare Intl to Cayman Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
O'Hare Intl and Cayman Islands flights
Browse other O'Hare Intl and Cayman Islands flight options. Last updated on March 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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Consider these flights traveling to Cayman Islands regions.
Top 2 airlines flying from O'Hare Intl to Cayman Islands
Discover the top 2 airlines that operate flights from O'Hare Intl to Cayman Islands. 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 11, 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% |