$131+ 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 6/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Jun 28 — Jul 51
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl to Cayman Islands with Cheapflights
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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 O'Hare Intl to Cayman Islands
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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 May 29, 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 May 29, 2026.
This Expedia deal was found by Cheapflights users on 5/26. 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 6/79:55 am
ORD
- GCM
1 stop25h 30m
Air Canada
Thu 6/1112:25 pm
GCM
- ORD
1 stop26h 30m
Air Canada
Deal found 5/26![Air Canada logo]()
$361
This FlightHub deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/32:15 pm
ORD
- GCM
1 stop21h 10m
Air Canada
Sat 6/610:55 am
GCM
- ORD
1 stop7h 56m
Air Canada
Deal found 5/28![Air Canada logo]()
$385
This Air Canada deal was found by Cheapflights users on 5/25. 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 6/79:55 am
ORD
- GCM
1 stop25h 30m
Air Canada
Mon 6/1512:25 pm
GCM
- ORD
1 stop25h 00m
Air Canada
Deal found 5/25![Air Canada logo]()
$387
This Orbitz deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:40 pm
ORD
- GCM
2 stops43h 50m
Air Canada
Sat 9/2612:25 pm
GCM
- ORD
1 stop26h 30m
Air Canada
Deal found 5/24![Air Canada logo]()
$410
This Air Canada deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/235:35 pm
ORD
- GCM
1 stop17h 55m
Air Canada
Sat 9/2612:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 5/29![Air Canada logo]()
$415
This Expedia deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:40 pm
ORD
- GCM
2 stops43h 50m
Air Canada
Sat 9/1912:25 pm
GCM
- ORD
1 stop24h 58m
Air Canada
Deal found 5/27![Air Canada logo]()
$418
This Travelocity deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/173:40 pm
ORD
- GCM
2 stops43h 50m
Air Canada
Sat 10/2412:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 5/27![Air Canada logo]()
$420
This Expedia deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:45 am
ORD
- GCM
2 stops49h 00m
Air Canada
Mon 9/712:25 pm
GCM
- ORD
1 stop26h 30m
Air Canada
Deal found 5/27![Air Canada logo]()
$442
This Orbitz deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/243:45 pm
ORD
- GCM
1 stop19h 15m
Air Canada
Sat 10/3112:10 pm
GCM
- ORD
1 stop23h 48m
Air Canada
Deal found 5/25![Air Canada logo]()
$451
This FlightHub deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:35 pm
ORD
- GCM
1 stop17h 55m
Air Canada
Sat 9/1912:25 pm
GCM
- ORD
1 stop19h 35m
Air Canada
Deal found 5/27![Air Canada logo]()
$454
This Mytrip deal was found by Cheapflights users on 5/26. 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 11/216:30 pm
ORD
- CYB
2 stops19h 55m
Multiple Airlines
Sat 11/287:10 am
CYB
- ORD
2 stops26h 50m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$976
This Justfly.com deal was found by Cheapflights users on 5/25. 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 6/218:40 pm
ORD
- CYB
2 stops21h 10m
Multiple Airlines
Mon 6/298:30 am
CYB
- ORD
2 stops27h 30m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$1,149
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 May 29, 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 May 29, 2026.
This Orbitz deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:40 pm
ORD
- GCM
2 stops43h 50m
Air Canada
Sat 9/2612:25 pm
GCM
- ORD
1 stop26h 30m
Air Canada
Deal found 5/24![Air Canada logo]()
$410
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:30 am
ORD
- GCM
1 stop6h 11m
Delta
Fri 9/1812:55 pm
GCM
- ORD
2 stops19h 07m
Delta
Deal found 5/27![Delta logo]()
$616
This American Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:00 pm
ORD
- GCM
1 stop16h 00m
American Airlines
Sat 9/2612:27 pm
GCM
- ORD
1 stop10h 04m
American Airlines
Deal found 5/24![American Airlines logo]()
$646
This Mytrip deal was found by Cheapflights users on 5/26. 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 11/216:30 pm
ORD
- CYB
2 stops19h 55m
Multiple Airlines
Sat 11/287:10 am
CYB
- ORD
2 stops26h 50m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$976
This Air Canada deal was found by Cheapflights users on 5/24. 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 11/73:55 pm
ORD
- GCM
2 stops19h 05m
Air Canada
Wed 11/111:10 pm
GCM
- ORD
1 stop20h 50m
Air Canada
Deal found 5/24![Air Canada logo]()
$530
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:25 pm
ORD
- GCM
2 stops16h 14m
Delta
Tue 9/812:56 pm
GCM
- ORD
2 stops19h 00m
Delta
Deal found 5/28![Delta logo]()
$631
This American Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:50 pm
ORD
- GCM
1 stop16h 40m
American Airlines
Sat 9/1211:55 am
GCM
- ORD
2 stops11h 55m
American Airlines
Deal found 5/26![American Airlines logo]()
$651
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:30 am
ORD
- GCM
1 stop6h 10m
Delta
Thu 9/1712:55 pm
GCM
- ORD
1 stop8h 00m
Delta
Deal found 5/27![Delta logo]()
$646
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/145:30 am
ORD
- GCM
1 stop6h 10m
Delta
Sun 9/2012:55 pm
GCM
- ORD
1 stop8h 00m
Delta
Deal found 5/27![Delta logo]()
$646
This Justfly.com deal was found by Cheapflights users on 5/25. 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 6/218:40 pm
ORD
- CYB
2 stops21h 10m
Multiple Airlines
Mon 6/298:30 am
CYB
- ORD
2 stops27h 30m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$1,149
Last-minute flights from O'Hare Intl to Cayman IslandsDiscover last-minute flight deals from O'Hare Intl to Cayman Islands. Data last updated May 29, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Cayman Islands. Data last updated May 29, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/319:55 am
ORD
- GCM
1 stop25h 30m
Air Canada
Sat 6/610:55 am
GCM
- ORD
1 stop8h 30m
Air Canada
Deal found 5/28![Air Canada logo]()
$564
This FlightHub deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/32:15 pm
ORD
- GCM
1 stop21h 10m
Air Canada
Sat 6/610:55 am
GCM
- ORD
1 stop7h 56m
Air Canada
Deal found 5/28![Air Canada logo]()
$385
This Expedia deal was found by Cheapflights users on 5/26. 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 6/79:55 am
ORD
- GCM
1 stop25h 30m
Air Canada
Thu 6/1112:25 pm
GCM
- ORD
1 stop26h 30m
Air Canada
Deal found 5/26![Air Canada logo]()
$361
This Air Canada deal was found by Cheapflights users on 5/25. 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 6/79:55 am
ORD
- GCM
1 stop25h 30m
Air Canada
Mon 6/1512:25 pm
GCM
- ORD
1 stop25h 00m
Air Canada
Deal found 5/25![Air Canada logo]()
$387
This Justfly.com deal was found by Cheapflights users on 5/25. 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.
Mon 6/88:20 pm
ORD
- GCM
2 stops38h 05m
Multiple Airlines
Sat 6/1310:55 am
GCM
- ORD
1 stop22h 05m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$543
This Air Canada deal was found by Cheapflights users on 5/25. 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 6/102:15 pm
ORD
- GCM
1 stop21h 10m
Air Canada
Mon 6/1512:25 pm
GCM
- ORD
1 stop25h 00m
Air Canada
Deal found 5/25![Air Canada logo]()
$600
This Mytrip deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/198:40 pm
ORD
- GCM
1 stop13h 20m
Multiple Airlines
Tue 6/231:45 pm
GCM
- ORD
1 stop8h 20m
Multiple Airlines
Deal found 5/29![Multiple Airlines logo]()
$546
This Justfly.com deal was found by Cheapflights users on 5/25. 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 6/218:40 pm
ORD
- CYB
2 stops21h 10m
Multiple Airlines
Mon 6/298:30 am
CYB
- ORD
2 stops27h 30m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$1,149
This Travelocity deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/243:45 pm
ORD
- GCM
1 stop19h 40m
Multiple Airlines
Sat 6/272:10 pm
GCM
- ORD
1 stop18h 35m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$605
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 May 29, 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 May 29, 2026.
This Air Canada deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/248:40 pm
ORD
- GCM
1 stop14h 45m
Air Canada
Deal found 5/28![Air Canada logo]()
$131
This Travelocity deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/238:35 am
ORD
- GCM
2 stops50h 50m
Air Canada
Deal found 5/27![Air Canada logo]()
$134
This Air Canada deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/198:40 pm
ORD
- GCM
1 stop13h 20m
Air Canada
Deal found 5/28![Air Canada logo]()
$144
This Air Canada deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/263:45 pm
ORD
- GCM
1 stop19h 40m
Air Canada
Deal found 5/28![Air Canada logo]()
$158
This Orbitz deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:45 am
ORD
- GCM
2 stops50h 40m
Air Canada
Deal found 5/25![Air Canada logo]()
$160
This Air Canada deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/173:45 pm
ORD
- GCM
1 stop18h 15m
Air Canada
Deal found 5/24![Air Canada logo]()
$162
This Air Canada deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/245:35 pm
ORD
- GCM
1 stop16h 25m
Air Canada
Deal found 5/28![Air Canada logo]()
$175
This Air Canada deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:30 pm
ORD
- GCM
1 stop16h 30m
Air Canada
Deal found 5/29![Air Canada logo]()
$191
This Air Canada deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/218:40 pm
ORD
- GCM
1 stop14h 45m
Air Canada
Deal found 5/28![Air Canada logo]()
$193
This Expedia deal was found by Cheapflights users on 5/26. 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.
Sat 8/228:45 am
ORD
- GCM
2 stops50h 40m
Air Canada
Deal found 5/26![Air Canada logo]()
$197
This Air Canada deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/236:21 pm
ORD
- GCM
2 stops17h 04m
Air Canada
Deal found 5/28![Air Canada logo]()
$199
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 May 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $387 (Expedia) |
One-way from | $131 (Air Canada) |
Popular in | December |
Cheapest in | February |
Average price | $700 |
Good round-trip deal | $666 or less |
Good one-way deal | $384 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 May 29, 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
Sat 9/19
3:40 pm-11:30 am
2 stops43h 50m
George Town Owen Roberts Intl
Sat 9/26
12:25 pm-2:55 pm
1 stop26h 30m
$410
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 11/7
3:55 pm-12:00 pm
2 stops19h 05m
George Town Owen Roberts Intl
Wed 11/11
1:10 pm-9:00 am
1 stop20h 50m
$530
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 9/9
5:30 am-11:41 am
1 stop6h 11m
George Town Owen Roberts Intl
Fri 9/18
12:55 pm-8:02 am
2 stops19h 07m
$616
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Fri 9/4
7:25 pm-11:39 am
2 stops16h 14m
George Town Owen Roberts Intl
Tue 9/8
12:56 pm-7:56 am
2 stops19h 00m
$631
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 9/19
7:00 pm-11:00 am
1 stop16h 00m
George Town Owen Roberts Intl
Sat 9/26
12:27 pm-10:31 pm
1 stop10h 04m
$646
Quickest round-trip
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Thu 9/10
5:30 am-11:40 am
1 stop6h 10m
George Town Owen Roberts Intl
Thu 9/17
12:55 pm-8:55 pm
1 stop8h 00m
$646
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Mon 9/14
5:30 am-11:40 am
1 stop6h 10m
George Town Owen Roberts Intl
Sun 9/20
12:55 pm-8:55 pm
1 stop8h 00m
$646
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 9/5
6:50 pm-11:30 am
1 stop16h 40m
George Town Owen Roberts Intl
Sat 9/12
11:55 am-11:50 pm
2 stops11h 55m
$651
ChicagoCayman Brac
ORD - CYB
ORDCYB
Chicago O'Hare Intl
Sat 11/21
6:30 pm-3:25 pm
2 stops19h 55m
Cayman Brac Gerrard-Smith
Sat 11/28
7:10 am-9:00 am
2 stops26h 50m
$976
ChicagoCayman Brac
ORD - CYB
ORDCYB
Chicago O'Hare Intl
Sun 6/21
8:40 pm-5:50 pm
2 stops21h 10m
Cayman Brac Gerrard-Smith
Mon 6/29
8:30 am-12:00 pm
2 stops27h 30m
$1,149
Showing 1-10 of 21 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 $174). Flying from Chicago O'Hare Intl Airport to Cayman Islands in September is currently the most expensive (average of $659). 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 May 29, 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 May 29, 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.
Comfort
7.3
Overall
7.4
Entertainment
7.1
Food
6.6
Crew
8.1
Boarding
7.7
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Comfort
7.3
Overall
7.4
Entertainment
7.1
Food
6.6
Crew
8.1
Boarding
7.7
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Comfort
7.3
Overall
7.4
Entertainment
7.1
Food
6.6
Crew
8.1
Boarding
7.7
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
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
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Search flights from O'Hare Intl to Cayman Islands by cabin class
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O'Hare Intl and Cayman Islands flights
Browse other O'Hare Intl and Cayman Islands flight options. Last updated on May 29, 2026.
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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 May 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$608 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$438 | Average$675 | FlexibilityNo cancel fee | On-time71% |