$148+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Aug 27 — Sep 31
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 July 28, 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 July 28, 2026.
This Travelocity deal was found by Cheapflights users on 7/25. 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 Travelocity 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 50m
Air Canada
Sat 9/2610:40 am
GCM
- ORD
1 stop28h 15m
Air Canada
Deal found 7/25![Air Canada logo]()
$394
This Expedia deal was found by Cheapflights users on 7/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:45 am
ORD
- GCM
2 stops26h 40m
Air Canada
Mon 9/2112:25 pm
GCM
- ORD
2 stops26h 27m
Air Canada
Deal found 7/25![Air Canada logo]()
$400
This Air Canada deal was found by Cheapflights users on 7/25. 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 9/165:53 pm
ORD
- GCM
1 stop17h 32m
Air Canada
Sat 9/1910:40 am
GCM
- ORD
1 stop22h 20m
Air Canada
Deal found 7/25![Air Canada logo]()
$412
This Flightnetwork deal was found by Cheapflights users on 7/26. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:45 pm
ORD
- GCM
1 stop19h 40m
Multiple Airlines
Wed 9/167:00 am
GCM
- ORD
2 stops36h 48m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$446
This Air Canada deal was found by Cheapflights users on 7/26. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:40 pm
ORD
- GCM
1 stop14h 50m
Air Canada
Sat 10/3112:10 pm
GCM
- ORD
1 stop8h 03m
Air Canada
Deal found 7/26![Air Canada logo]()
$455
This Gotogate deal was found by Cheapflights users on 7/28. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:35 pm
ORD
- GCM
1 stop16h 10m
Multiple Airlines
Fri 9/187:00 am
GCM
- ORD
2 stops36h 48m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$457
This Expedia deal was found by Cheapflights users on 7/26. 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.
Wed 9/92:15 pm
ORD
- CYB
2 stops41h 50m
Multiple Airlines
Wed 9/163:55 pm
CYB
- ORD
2 stops46h 55m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$741
This FlightHub deal was found by Cheapflights users on 7/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/308:50 pm
ORD
- CYB
2 stops35h 15m
Multiple Airlines
Mon 9/78:30 am
CYB
- ORD
2 stops24h 30m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$1,008
This FlightHub deal was found by Cheapflights users on 7/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/308:50 pm
ORD
- CYB
2 stops18h 35m
Multiple Airlines
Sun 9/66:20 pm
CYB
- ORD
2 stops25h 33m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$1,066
This Mytrip deal was found by Cheapflights users on 7/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/269:50 am
ORD
- CYB
2 stops32h 00m
Multiple Airlines
Wed 9/26:20 pm
CYB
- ORD
2 stops25h 32m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$1,143
This FlightHub deal was found by Cheapflights users on 7/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/318:40 pm
ORD
- CYB
2 stops21h 10m
Multiple Airlines
Mon 8/38:30 am
CYB
- ORD
2 stops30h 25m
Multiple Airlines
Deal found 7/24![Multiple Airlines logo]()
$1,508
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 July 28, 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 July 28, 2026.
This Travelocity deal was found by Cheapflights users on 7/25. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:35 pm
ORD
- GCM
1 stop17h 50m
Air Canada
Sat 9/2610:40 am
GCM
- ORD
2 stops23h 35m
Air Canada
Deal found 7/25![Air Canada logo]()
$397
This FlightHub deal was found by Cheapflights users on 7/28. 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 9/168:40 pm
ORD
- GCM
1 stop14h 45m
Multiple Airlines
Wed 9/237:00 am
GCM
- ORD
2 stops26h 00m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$470
This Delta deal was found by Cheapflights users on 7/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:27 am
ORD
- GCM
1 stop6h 13m
Delta
Fri 11/201:50 pm
GCM
- ORD
1 stop11h 09m
Delta
Deal found 7/26![Delta logo]()
$631
This American Airlines deal was found by Cheapflights users on 7/24. 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 10/105:05 am
ORD
- GCM
1 stop13h 55m
American Airlines
Sat 10/1712:00 pm
GCM
- ORD
1 stop9h 30m
American Airlines
Deal found 7/24![American Airlines logo]()
$681
This Air Canada deal was found by Cheapflights users on 7/28. 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.
Sat 10/243:40 pm
ORD
- GCM
2 stops19h 30m
Air Canada
Wed 10/2812:10 pm
GCM
- ORD
1 stop8h 03m
Air Canada
Deal found 7/28![Air Canada logo]()
$455
This Delta deal was found by Cheapflights users on 7/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:29 pm
ORD
- GCM
2 stops18h 11m
Delta
Mon 11/161:50 pm
GCM
- ORD
2 stops18h 56m
Delta
Deal found 7/26![Delta logo]()
$661
This American Airlines deal was found by Cheapflights users on 7/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:43 am
ORD
- GCM
1 stop10h 17m
American Airlines
Sat 10/2412:25 pm
GCM
- ORD
1 stop7h 26m
American Airlines
Deal found 7/27![American Airlines logo]()
$681
This Expedia deal was found by Cheapflights users on 7/26. 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.
Wed 9/92:15 pm
ORD
- CYB
2 stops41h 50m
Multiple Airlines
Wed 9/163:55 pm
CYB
- ORD
2 stops46h 55m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$741
This Delta deal was found by Cheapflights users on 7/28. 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 9/115:30 am
ORD
- GCM
1 stop6h 10m
Delta
Fri 9/181:00 pm
GCM
- ORD
1 stop10h 59m
Delta
Deal found 7/28![Delta logo]()
$681
This American Airlines deal was found by Cheapflights users on 7/24. 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 9/56:00 am
ORD
- GCM
1 stop8h 17m
American Airlines
Sat 9/1212:36 pm
GCM
- ORD
1 stop9h 55m
American Airlines
Deal found 7/24![American Airlines logo]()
$681
This Delta deal was found by Cheapflights users on 7/28. 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.
Wed 9/95:30 am
ORD
- GCM
1 stop6h 10m
Delta
Sun 9/131:00 pm
GCM
- ORD
1 stop10h 59m
Delta
Deal found 7/28![Delta logo]()
$681
This Mytrip deal was found by Cheapflights users on 7/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/269:50 am
ORD
- CYB
2 stops32h 00m
Multiple Airlines
Wed 9/26:20 pm
CYB
- ORD
2 stops25h 32m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$1,143
Last-minute flights from O'Hare Intl to Cayman IslandsDiscover last-minute flight deals from O'Hare Intl to Cayman Islands. Data last updated July 28, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Cayman Islands. Data last updated July 28, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 7/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/318:40 pm
ORD
- CYB
2 stops21h 10m
Multiple Airlines
Mon 8/38:30 am
CYB
- ORD
2 stops30h 25m
Multiple Airlines
Deal found 7/24![Multiple Airlines logo]()
$1,508
This American Airlines deal was found by Cheapflights users on 7/24. 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.
Wed 8/125:00 am
ORD
- GCM
1 stop6h 00m
American Airlines
Sun 8/1612:00 pm
GCM
- ORD
1 stop12h 35m
American Airlines
Deal found 7/24![American Airlines logo]()
$711
This American Airlines deal was found by Cheapflights users on 7/23. 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 8/156:00 am
ORD
- GCM
1 stop7h 10m
American Airlines
Sat 8/2212:30 pm
GCM
- ORD
1 stop7h 16m
American Airlines
Deal found 7/23![American Airlines logo]()
$726
This American Airlines deal was found by Cheapflights users on 7/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:00 am
ORD
- GCM
1 stop7h 17m
American Airlines
Mon 8/1712:30 pm
GCM
- ORD
1 stop11h 22m
American Airlines
Deal found 7/25![American Airlines logo]()
$771
This American Airlines deal was found by Cheapflights users on 7/26. 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.
Sun 8/168:53 pm
ORD
- GCM
2 stops14h 07m
American Airlines
Thu 8/2012:30 pm
GCM
- ORD
1 stop7h 16m
American Airlines
Deal found 7/26![American Airlines logo]()
$736
This Travelocity deal was found by Cheapflights users on 7/27. 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.
Fri 8/213:45 pm
ORD
- GCM
1 stop18h 00m
Air Canada
Mon 8/2412:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 7/27![Air Canada logo]()
$709
This American Airlines deal was found by Cheapflights users on 7/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
ORD
- GCM
1 stop8h 17m
American Airlines
Wed 8/262:10 pm
GCM
- ORD
1 stop10h 25m
American Airlines
Deal found 7/25![American Airlines logo]()
$681
This Orbitz deal was found by Cheapflights users on 7/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/269:50 am
ORD
- GCM
1 stop25h 35m
Air Canada
Mon 8/3112:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 7/28![Air Canada logo]()
$609
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:05 am
ORD
- GCM
2 stops8h 05m
American Airlines
Mon 8/3112:00 pm
GCM
- ORD
1 stop11h 30m
American Airlines
Deal found 7/28![American Airlines logo]()
$691
This Mytrip deal was found by Cheapflights users on 7/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/269:50 am
ORD
- CYB
2 stops32h 00m
Multiple Airlines
Wed 9/26:20 pm
CYB
- ORD
2 stops25h 32m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$1,143
This FlightHub deal was found by Cheapflights users on 7/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/308:50 pm
ORD
- CYB
2 stops35h 15m
Multiple Airlines
Mon 9/78:30 am
CYB
- ORD
2 stops24h 30m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$1,008
This FlightHub deal was found by Cheapflights users on 7/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/308:50 pm
ORD
- CYB
2 stops18h 35m
Multiple Airlines
Sun 9/66:20 pm
CYB
- ORD
2 stops25h 33m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$1,066
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 July 28, 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 July 28, 2026.
This Expedia deal was found by Cheapflights users on 7/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/232:15 pm
ORD
- GCM
1 stop21h 10m
Air Canada
Deal found 7/25![Air Canada logo]()
$148
This Flightnetwork deal was found by Cheapflights users on 7/26. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:45 pm
ORD
- GCM
1 stop19h 40m
Air Canada
Deal found 7/26![Air Canada logo]()
$153
This Air Canada deal was found by Cheapflights users on 7/26. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/273:45 pm
ORD
- GCM
1 stop19h 40m
Air Canada
Deal found 7/26![Air Canada logo]()
$165
This Air Canada deal was found by Cheapflights users on 7/27. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:45 am
ORD
- GCM
2 stops25h 00m
Air Canada
Deal found 7/27![Air Canada logo]()
$168
This Expedia deal was found by Cheapflights users on 7/26. 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 10/253:45 pm
ORD
- GCM
2 stops43h 25m
Air Canada
Deal found 7/26![Air Canada logo]()
$170
This Air Canada deal was found by Cheapflights users on 7/24. 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.
Sun 9/206:21 pm
ORD
- GCM
2 stops17h 04m
Air Canada
Deal found 7/24![Air Canada logo]()
$180
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 July 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $394 (Travelocity) |
One-way from | $148 (Expedia) |
Popular in | July |
Cheapest in | February |
Average price | $986 |
Good round-trip deal | $701 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 July 28, 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
Wed 9/16
5:35 pm-11:25 am
1 stop17h 50m
George Town Owen Roberts Intl
Sat 9/26
10:40 am-10:15 am
2 stops23h 35m
$397
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 10/24
3:40 pm-11:10 am
2 stops19h 30m
George Town Owen Roberts Intl
Wed 10/28
12:10 pm-8:13 pm
1 stop8h 03m
$455
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 9/16
8:40 pm-11:25 am
1 stop14h 45m
George Town Owen Roberts Intl
Wed 9/23
7:00 am-9:00 am
2 stops26h 00m
$470
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 10/25
5:27 am-11:40 am
1 stop6h 13m
George Town Owen Roberts Intl
Fri 11/20
1:50 pm-11:59 pm
1 stop11h 09m
$631
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 10/25
5:29 pm-11:40 am
2 stops18h 11m
George Town Owen Roberts Intl
Mon 11/16
1:50 pm-7:46 am
2 stops18h 56m
$661
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 10/10
5:05 am-7:00 pm
1 stop13h 55m
George Town Owen Roberts Intl
Sat 10/17
12:00 pm-9:30 pm
1 stop9h 30m
$681
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 10/17
8:43 am-7:00 pm
1 stop10h 17m
George Town Owen Roberts Intl
Sat 10/24
12:25 pm-7:51 pm
1 stop7h 26m
$681
Quickest round-trip
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Fri 9/11
5:30 am-11:40 am
1 stop6h 10m
George Town Owen Roberts Intl
Fri 9/18
1:00 pm-11:59 pm
1 stop10h 59m
$681
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 9/5
6:00 am-2:17 pm
1 stop8h 17m
George Town Owen Roberts Intl
Sat 9/12
12:36 pm-10:31 pm
1 stop9h 55m
$681
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 9/9
5:30 am-11:40 am
1 stop6h 10m
George Town Owen Roberts Intl
Sun 9/13
1:00 pm-11:59 pm
1 stop10h 59m
$681
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, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Cayman Islands (average of $530). Flying from Chicago O'Hare Intl Airport to Cayman Islands in November is currently the most expensive (average of $938). 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 July 28, 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 July 28, 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.
Boarding
7.7
Crew
8.1
Comfort
7.3
Entertainment
7.1
Food
6.6
Overall
7.4
Reviews
1 / 20
8.0
ExcellentRuth,Dec 2024
ORD - AMS
Boarding
7.7
Crew
8.1
Comfort
7.3
Entertainment
7.1
Food
6.6
Overall
7.4
Reviews
1 / 20
8.0
ExcellentRuth,Dec 2024
ORD - AMS
Boarding
7.7
Crew
8.1
Comfort
7.3
Entertainment
7.1
Food
6.6
Overall
7.4
Reviews
1 / 20
8.0
ExcellentRuth,Dec 2024
ORD - AMS
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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O'Hare Intl and Cayman Islands flights
Browse other O'Hare Intl and Cayman Islands flight options. Last updated on July 28, 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 July 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$614 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$447 | Average$688 | FlexibilityNo cancel fee | On-time71% |