$94+ Cheap flights from Chicago (CHI) 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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
May 1 — May 81
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Cayman Islands with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Cayman Islands
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Cheapest flights from Chicago to Cayman IslandsExplore the most affordable flight options available from Chicago to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2026.
Explore the most affordable flight options available from Chicago to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2026.
This FlightHub deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/45:05 am
ORD
- GCM
1 stop7h 15m
Spirit Airlines
Thu 4/91:52 pm
GCM
- ORD
1 stop9h 25m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$339
This Expedia deal was found by Cheapflights users on 3/31. 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.
Fri 6/59:55 am
ORD
- GCM
1 stop24h 05m
Air Canada
Mon 6/812:25 pm
GCM
- ORD
1 stop20h 40m
Air Canada
Deal found 3/31![Air Canada logo]()
$345
This Expedia deal was found by Cheapflights users on 3/28. 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 Expedia 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
Multiple Airlines
Thu 4/1611:55 am
GCM
- ORD
1 stop25h 10m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$346
This Travelocity deal was found by Cheapflights users on 3/30. 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.
Sun 6/218:40 pm
ORD
- GCM
1 stop14h 45m
Air Canada
Mon 6/2912:25 pm
GCM
- ORD
1 stop24h 57m
Air Canada
Deal found 3/30![Air Canada logo]()
$360
This Air Canada deal was found by Cheapflights users on 3/31. 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 5/298:20 pm
ORD
- GCM
1 stop13h 40m
Air Canada
Thu 6/412:25 pm
GCM
- ORD
1 stop20h 40m
Air Canada
Deal found 3/31![Air Canada logo]()
$363
This Expedia deal was found by Cheapflights users on 3/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/293:50 pm
ORD
- GCM
1 stop18h 10m
Air Canada
Mon 6/112:25 pm
GCM
- ORD
2 stops21h 53m
Air Canada
Deal found 3/29![Air Canada logo]()
$366
This Southwest deal was found by Cheapflights users on 3/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:00 am
MDW
- GCM
1 stop6h 10m
Southwest
Tue 5/51:05 pm
GCM
- MDW
2 stops18h 30m
Southwest
Deal found 3/29![Southwest logo]()
$507
This Southwest deal was found by Cheapflights users on 3/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/198:55 pm
MDW
- GCM
2 stops15h 15m
Southwest
Tue 4/281:05 pm
GCM
- MDW
2 stops8h 45m
Southwest
Deal found 3/29![Southwest logo]()
$528
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:35 am
MDW
- GCM
1 stop6h 35m
Southwest
Fri 5/81:05 pm
GCM
- MDW
1 stop7h 35m
Southwest
Deal found 3/31![Southwest logo]()
$530
This Kiwi.com deal was found by Cheapflights users on 3/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:00 am
MDW
- GCM
2 stops15h 15m
Multiple Airlines
Sat 5/161:45 pm
GCM
- MDW
1 stop20h 00m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$552
This Southwest deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/235:35 am
MDW
- GCM
1 stop6h 35m
Southwest
Wed 4/291:05 pm
GCM
- MDW
1 stop8h 20m
Southwest
Deal found 4/1![Southwest logo]()
$575
This Delta deal was found by Cheapflights users on 4/1. 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 5/36:38 pm
MDW
- GCM
2 stops17h 22m
Delta
Fri 5/291:19 pm
GCM
- MDW
1 stop7h 50m
Delta
Deal found 4/1![Delta logo]()
$600
Best flights from Chicago to Cayman IslandsDiscover carefully curated flight deals from Chicago to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 1, 2026.
Discover carefully curated flight deals from Chicago to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 1, 2026.
This Southwest deal was found by Cheapflights users on 3/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:15 pm
ORD
- GCM
2 stops16h 55m
Southwest
Wed 5/201:05 pm
GCM
- ORD
1 stop8h 50m
Southwest
Deal found 3/29![Southwest logo]()
$497
This United Airlines deal was found by Cheapflights users on 3/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/198:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Tue 4/281:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/27![United Airlines logo]()
$581
This American Airlines deal was found by Cheapflights users on 3/31. 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 4/265:00 am
ORD
- GCM
1 stop6h 00m
American Airlines
Wed 4/2912:00 pm
GCM
- ORD
2 stops9h 21m
American Airlines
Deal found 3/31![American Airlines logo]()
$600
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/57:01 am
ORD
- GCM
2 stops28h 30m
Delta
Fri 8/712:56 pm
GCM
- ORD
1 stop7h 37m
Delta
Deal found 3/30![Delta logo]()
$616
This Southwest deal was found by Cheapflights users on 3/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:00 am
MDW
- GCM
1 stop6h 10m
Southwest
Tue 5/51:05 pm
GCM
- MDW
1 stop6h 40m
Southwest
Deal found 3/29![Southwest logo]()
$516
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:35 am
MDW
- GCM
1 stop6h 35m
Southwest
Fri 5/81:05 pm
GCM
- MDW
1 stop7h 35m
Southwest
Deal found 3/31![Southwest logo]()
$530
This Delta deal was found by Cheapflights users on 4/1. 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 5/36:38 pm
MDW
- GCM
2 stops17h 22m
Delta
Sun 5/311:19 pm
GCM
- MDW
1 stop7h 50m
Delta
Deal found 4/1![Delta logo]()
$625
This United Airlines deal was found by Cheapflights users on 3/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/248:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Mon 4/271:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/27![United Airlines logo]()
$631
This United Airlines deal was found by Cheapflights users on 3/30. 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 5/99:29 am
ORD
- GCM
Nonstop4h 01m
United Airlines
Sat 5/161:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/30![United Airlines logo]()
$631
This Southwest deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/235:35 am
MDW
- GCM
1 stop6h 35m
Southwest
Wed 4/291:05 pm
GCM
- MDW
1 stop8h 20m
Southwest
Deal found 4/1![Southwest logo]()
$575
This Delta deal was found by Cheapflights users on 3/28. 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.
Sat 5/96:23 am
MDW
- GCM
1 stop5h 31m
Delta
Sat 5/161:19 pm
GCM
- MDW
1 stop7h 50m
Delta
Deal found 3/28![Delta logo]()
$645
This United Airlines deal was found by Cheapflights users on 3/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/215:30 am
ORD
- GCM
1 stop7h 00m
United Airlines
Sat 7/251:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/28![United Airlines logo]()
$636
This Delta deal was found by Cheapflights users on 3/27. 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.
Sun 8/236:00 am
MDW
- GCM
1 stop5h 41m
Delta
Sat 8/2912:56 pm
GCM
- MDW
1 stop8h 50m
Delta
Deal found 3/27![Delta logo]()
$646
This Delta deal was found by Cheapflights users on 3/27. 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.
Sat 8/226:00 am
MDW
- GCM
1 stop5h 41m
Delta
Wed 8/2612:56 pm
GCM
- MDW
1 stop8h 50m
Delta
Deal found 3/27![Delta logo]()
$646
This United Airlines deal was found by Cheapflights users on 3/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:30 am
ORD
- GCM
1 stop7h 00m
United Airlines
Sat 6/61:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/28![United Airlines logo]()
$678
This United Airlines deal was found by Cheapflights users on 3/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/268:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Wed 4/291:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/28![United Airlines logo]()
$701
Last-minute flights from Chicago to Cayman IslandsDiscover last-minute flight deals from Chicago to Cayman Islands. Data last updated April 1, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Cayman Islands. Data last updated April 1, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/45:05 am
ORD
- GCM
1 stop7h 15m
Spirit Airlines
Thu 4/91:52 pm
GCM
- ORD
1 stop9h 25m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$339
This Expedia deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/66:40 pm
ORD
- GCM
1 stop16h 30m
Air Canada
Mon 4/1311:25 am
GCM
- ORD
1 stop27h 50m
Air Canada
Deal found 3/30![Air Canada logo]()
$407
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 4/66:30 am
MDW
- GCM
1 stop14h 45m
Multiple Airlines
Mon 4/131:50 pm
GCM
- MDW
1 stop20h 25m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$703
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:10 pm
ORD
- GCM
1 stop18h 47m
Multiple Airlines
Sat 4/111:15 pm
GCM
- ORD
1 stop6h 56m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$383
This Expedia deal was found by Cheapflights users on 3/28. 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 Expedia 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
Multiple Airlines
Thu 4/1611:55 am
GCM
- ORD
1 stop25h 10m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 Kiwi.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
Multiple Airlines
Wed 4/1511:30 am
GCM
- ORD
1 stop25h 35m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$386
This Southwest deal was found by Cheapflights users on 3/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
MDW
- GCM
1 stop6h 50m
Southwest
Wed 4/151:05 pm
GCM
- MDW
1 stop6h 40m
Southwest
Deal found 3/29![Southwest logo]()
$667
This Air Canada deal was found by Cheapflights users on 3/30. 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 4/132:00 pm
ORD
- GCM
1 stop21h 10m
Air Canada
Thu 4/1611:55 am
GCM
- ORD
1 stop27h 20m
Air Canada
Deal found 3/30![Air Canada logo]()
$410
This Southwest deal was found by Cheapflights users on 3/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/198:55 pm
MDW
- GCM
2 stops15h 15m
Southwest
Tue 4/281:05 pm
GCM
- MDW
2 stops8h 45m
Southwest
Deal found 3/29![Southwest logo]()
$528
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/197:30 am
MDW
- GCM
1 stop10h 30m
Multiple Airlines
Tue 4/281:45 pm
GCM
- MDW
1 stop20h 30m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$621
This Southwest deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/235:35 am
MDW
- GCM
1 stop6h 35m
Southwest
Wed 4/291:05 pm
GCM
- MDW
1 stop8h 20m
Southwest
Deal found 4/1![Southwest logo]()
$575
This Southwest deal was found by Cheapflights users on 3/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/288:50 pm
MDW
- GCM
2 stops15h 20m
Southwest
Tue 5/51:05 pm
GCM
- MDW
2 stops18h 30m
Southwest
Deal found 3/29![Southwest logo]()
$507
One-way flights from Chicago to Cayman IslandsSearch for one-way flight options from Chicago to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
Search for one-way flight options from Chicago to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
This Priceline deal was found by Cheapflights users on 3/28. 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 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 3/28![Spirit Airlines logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 3/28. 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 Kiwi.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 3/28![Spirit Airlines logo]()
$123
This Air Canada deal was found by Cheapflights users on 3/31. 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.
Tue 6/21:55 pm
ORD
- GCM
2 stops45h 30m
Air Canada
Deal found 3/31![Air Canada logo]()
$128
This Expedia deal was found by Cheapflights users on 3/31. 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.
Fri 5/299:55 am
ORD
- GCM
1 stop24h 05m
Air Canada
Deal found 3/31![Air Canada logo]()
$141
This Expedia deal was found by Cheapflights users on 3/27. 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.
Tue 5/268:45 am
ORD
- GCM
2 stops50h 40m
Air Canada
Deal found 3/27![Air Canada logo]()
$144
This Air Canada deal was found by Cheapflights users on 3/31. 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 5/2710:41 am
ORD
- GCM
2 stops24h 44m
Air Canada
Deal found 3/31![Air Canada logo]()
$146
This Air Canada deal was found by Cheapflights users on 3/31. 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 9/275:35 pm
ORD
- GCM
1 stop17h 55m
Air Canada
Deal found 3/31![Air Canada logo]()
$148
This Air Canada deal was found by Cheapflights users on 3/29. 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.
Sun 4/267:13 am
ORD
- GCM
2 stops27h 02m
Air Canada
Deal found 3/29![Air Canada logo]()
$149
This Mytrip deal was found by Cheapflights users on 3/31. 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 4/186:40 am
ORD
- GCM
2 stops8h 10m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$150
This Expedia deal was found by Cheapflights users on 3/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/285:35 pm
ORD
- GCM
1 stop17h 50m
Air Canada
Deal found 3/29![Air Canada logo]()
$151
This Priceline deal was found by Cheapflights users on 3/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/111:55 pm
ORD
- GCM
2 stops21h 00m
Air Canada
Deal found 3/28![Air Canada logo]()
$153
This Expedia deal was found by Cheapflights users on 3/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/273:40 pm
ORD
- GCM
2 stops43h 45m
Air Canada
Deal found 3/28![Air Canada logo]()
$154
Find flight deals from Chicago to Cayman Islands
Keep the following information in mind while searching for Chicago to Cayman Islands flight deals. Data was last updated April 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $345 (Expedia) |
One-way from | $94 (Priceline) |
Popular in | December |
Cheapest in | February |
Average price | $637 |
Good round-trip deal | $580 or less |
Good one-way deal | $256 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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 April 1, 2026.
Use the filters below to find and compare flights from Chicago 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 5/13
7:15 pm-12:10 pm
2 stops16h 55m
George Town Owen Roberts Intl
Wed 5/20
1:05 pm-9:55 pm
1 stop8h 50m
$497
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Tue 4/28
6:00 am-12:10 pm
1 stop6h 10m
George Town Owen Roberts Intl
Tue 5/5
1:05 pm-7:45 pm
1 stop6h 40m
$516
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Fri 5/1
5:35 am-12:10 pm
1 stop6h 35m
George Town Owen Roberts Intl
Fri 5/8
1:05 pm-8:40 pm
1 stop7h 35m
$530
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Thu 4/23
5:35 am-12:10 pm
1 stop6h 35m
George Town Owen Roberts Intl
Wed 4/29
1:05 pm-9:25 pm
1 stop8h 20m
$575
Quickest round-trip
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 4/19
8:45 am-12:45 pm
Nonstop4h 00m
George Town Owen Roberts Intl
Tue 4/28
1:50 pm-6:13 pm
Nonstop4h 23m
$581
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 4/26
5:00 am-11:00 am
1 stop6h 00m
George Town Owen Roberts Intl
Wed 4/29
12:00 pm-9:21 pm
2 stops9h 21m
$600
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 8/5
7:01 am-11:31 am
2 stops28h 30m
George Town Owen Roberts Intl
Fri 8/7
12:56 pm-8:33 pm
1 stop7h 37m
$616
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Sun 5/3
6:38 pm-12:00 pm
2 stops17h 22m
George Town Owen Roberts Intl
Sun 5/31
1:19 pm-9:09 pm
1 stop7h 50m
$625
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Fri 4/24
8:45 am-12:45 pm
Nonstop4h 00m
George Town Owen Roberts Intl
Mon 4/27
1:50 pm-6:13 pm
Nonstop4h 23m
$631
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 5/9
9:29 am-1:30 pm
Nonstop4h 01m
George Town Owen Roberts Intl
Sat 5/16
1:50 pm-6:13 pm
Nonstop4h 23m
$631
Showing 1-10 of 38 resultsSorted by cheapest first
Best time to book a flight from Chicago to Cayman Islands
Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Chicago with our price prediction graph.
ORD-GCM
MDW-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 to the Cayman Islands
CHI-KY0
ORD-GCM
MDW-GCM
ORD-CYB
What is the cheapest month to book a flight from Chicago to Cayman Islands?
Currently, December is the cheapest month in which you can book a flight from Chicago to Cayman Islands (average of $322). Flying from Chicago 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 CHI to KY?
Find hourly flight availability from Chicago 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 April 1, 2026.
When flying from Chicago 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 April 1, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Chicago to the Cayman Islands. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Chicago 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 Chicago to Cayman Islands
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Complete your trip
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Find flights from Chicago to Cayman Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Cayman Islands flights
Browse other Chicago and Cayman Islands flight options. Last updated on April 1, 2026.
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Check out other popular destinations found by fellow travelers in 2026
Fly to Cayman Islands regions
Consider these flights traveling to Cayman Islands regions.
Top 2 airlines flying from Chicago to Cayman Islands
Discover the top 2 airlines that operate flights from Chicago 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 April 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$601 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$429 | Average$669 | FlexibilityNo cancel fee | On-time71% |