$170+ 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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Aug 14 — Aug 211
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 July 15, 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 July 15, 2026.
This Southwest deal was found by Cheapflights users on 7/15. 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 11/38:50 pm
MDW
- GCM
2 stops14h 45m
Southwest
Thu 11/121:30 pm
GCM
- MDW
2 stops10h 10m
Southwest
Deal found 7/15![Southwest logo]()
$396
This Air Canada deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada 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
Air Canada
Thu 9/1712:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 7/11![Air Canada logo]()
$429
This Expedia deal was found by Cheapflights users on 7/14. 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
Mon 9/2812:25 pm
GCM
- ORD
1 stop24h 58m
Air Canada
Deal found 7/14![Air Canada logo]()
$439
This Southwest deal was found by Cheapflights users on 7/15. 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 11/38:50 pm
MDW
- GCM
2 stops14h 45m
Southwest
Fri 11/131:30 pm
GCM
- MDW
2 stops10h 35m
Southwest
Deal found 7/15![Southwest logo]()
$450
This Air Canada deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:40 pm
ORD
- GCM
1 stop13h 05m
Air Canada
Thu 10/112:25 pm
GCM
- ORD
1 stop19h 35m
Air Canada
Deal found 7/13![Air Canada logo]()
$459
This Travelocity deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:40 pm
ORD
- GCM
2 stops43h 50m
Air Canada
Sat 10/1012:25 pm
GCM
- ORD
1 stop24h 58m
Air Canada
Deal found 7/10![Air Canada logo]()
$461
This Air Canada deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:40 pm
ORD
- GCM
1 stop14h 50m
Air Canada
Thu 10/812:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 7/13![Air Canada logo]()
$469
This Justfly.com deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com 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
Fri 10/3012:10 pm
GCM
- ORD
1 stop8h 03m
Air Canada
Deal found 7/12![Air Canada logo]()
$472
This Air Canada deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:21 pm
ORD
- GCM
2 stops17h 09m
Air Canada
Wed 10/2812:10 pm
GCM
- ORD
2 stops30h 10m
Air Canada
Deal found 7/12![Air Canada logo]()
$473
This Southwest deal was found by Cheapflights users on 7/14. 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 12/65:10 am
MDW
- GCM
1 stop6h 25m
Southwest
Wed 12/91:30 pm
GCM
- MDW
1 stop7h 05m
Southwest
Deal found 7/14![Southwest logo]()
$485
This Southwest deal was found by Cheapflights users on 7/14. 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 11/48:50 pm
MDW
- GCM
2 stops14h 45m
Southwest
Thu 11/121:30 pm
GCM
- MDW
1 stop6h 25m
Southwest
Deal found 7/14![Southwest logo]()
$514
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:05 pm
MDW
- GCM
2 stops17h 30m
Southwest
Mon 11/161:30 pm
GCM
- MDW
2 stops10h 10m
Southwest
Deal found 7/12![Southwest logo]()
$517
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 July 15, 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 July 15, 2026.
This Southwest deal was found by Cheapflights users on 7/14. 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 11/35:15 am
MDW
- GCM
1 stop6h 20m
Southwest
Thu 11/121:30 pm
GCM
- MDW
1 stop6h 25m
Southwest
Deal found 7/14![Southwest logo]()
$459
This Air Canada deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:50 pm
ORD
- GCM
1 stop14h 20m
Air Canada
Sat 11/281:10 pm
GCM
- ORD
1 stop7h 48m
Air Canada
Deal found 7/10![Air Canada logo]()
$499
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/36:00 am
MDW
- GCM
1 stop5h 40m
Delta
Wed 1/132:05 pm
GCM
- MDW
1 stop9h 05m
Delta
Deal found 7/12![Delta logo]()
$611
This United Airlines deal was found by Cheapflights users on 7/15. 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 1/105:00 am
ORD
- GCM
1 stop7h 15m
United Airlines
Fri 1/152:50 pm
GCM
- ORD
Nonstop4h 14m
United Airlines
Deal found 7/15![United Airlines logo]()
$621
This American Airlines deal was found by Cheapflights users on 7/15. 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.
Tue 11/310:30 am
ORD
- GCM
2 stops8h 50m
American Airlines
Fri 11/133:14 pm
GCM
- ORD
2 stops8h 46m
American Airlines
Deal found 7/15![American Airlines logo]()
$671
This Southwest deal was found by Cheapflights users on 7/15. 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.
Sat 8/295:00 am
MDW
- GCM
1 stop7h 05m
Southwest
Sat 9/51:00 pm
GCM
- MDW
1 stop7h 55m
Southwest
Deal found 7/15![Southwest logo]()
$586
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/185:30 am
ORD
- GCM
1 stop6h 10m
Delta
Fri 10/2312:55 pm
GCM
- ORD
1 stop8h 05m
Delta
Deal found 7/13![Delta logo]()
$631
This United Airlines deal was found by Cheapflights users on 7/14. 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 11/37:40 am
ORD
- GCM
1 stop7h 50m
United Airlines
Fri 11/135:45 pm
GCM
- ORD
1 stop15h 05m
United Airlines
Deal found 7/14![United Airlines logo]()
$631
This American Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/269:01 pm
ORD
- GCM
2 stops13h 59m
American Airlines
Tue 9/2912:00 pm
GCM
- ORD
2 stops10h 35m
American Airlines
Deal found 7/10![American Airlines logo]()
$676
This United Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:55 am
ORD
- GCM
1 stop8h 35m
United Airlines
Fri 11/135:45 pm
GCM
- ORD
1 stop17h 26m
United Airlines
Deal found 7/14![United Airlines logo]()
$631
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:30 am
ORD
- GCM
1 stop6h 10m
Delta
Mon 11/21:55 pm
GCM
- ORD
1 stop10h 56m
Delta
Deal found 7/12![Delta logo]()
$646
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:05 am
MDW
- GCM
1 stop5h 34m
Delta
Sat 9/121:05 pm
GCM
- MDW
1 stop9h 40m
Delta
Deal found 7/10![Delta logo]()
$681
This Gotogate deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/278:50 pm
ORD
- CYB
2 stops17h 35m
Multiple Airlines
Sat 1/210:55 am
CYB
- ORD
2 stops10h 03m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$1,788
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:05 am
MDW
- GCM
1 stop5h 34m
Delta
Wed 9/21:04 pm
GCM
- MDW
1 stop9h 32m
Delta
Deal found 7/12![Delta logo]()
$681
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:05 am
MDW
- GCM
1 stop5h 34m
Delta
Mon 8/311:04 pm
GCM
- MDW
1 stop9h 32m
Delta
Deal found 7/10![Delta logo]()
$681
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Sun 9/131:00 pm
GCM
- ORD
1 stop7h 55m
Delta
Deal found 7/12![Delta logo]()
$681
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:30 am
ORD
- GCM
1 stop6h 09m
Delta
Wed 9/21:04 pm
GCM
- ORD
1 stop10h 53m
Delta
Deal found 7/12![Delta logo]()
$681
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:30 am
ORD
- GCM
1 stop6h 09m
Delta
Mon 8/311:04 pm
GCM
- ORD
1 stop10h 53m
Delta
Deal found 7/10![Delta logo]()
$681
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/65:30 am
ORD
- GCM
1 stop6h 09m
Delta
Fri 9/111:00 pm
GCM
- ORD
1 stop7h 55m
Delta
Deal found 7/13![Delta logo]()
$681
Last-minute flights from Chicago to Cayman IslandsDiscover last-minute flight deals from Chicago to Cayman Islands. Data last updated July 15, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Cayman Islands. Data last updated July 15, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/295:10 am
MDW
- GCM
1 stop6h 45m
Southwest
Thu 7/3012:50 pm
GCM
- MDW
1 stop7h 20m
Southwest
Deal found 7/13![Southwest logo]()
$666
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:00 am
ORD
- GCM
1 stop7h 10m
American Airlines
Mon 8/1712:30 pm
GCM
- ORD
1 stop7h 16m
American Airlines
Deal found 7/13![American Airlines logo]()
$661
This American Airlines deal was found by Cheapflights users on 7/14. 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 8/126:00 am
ORD
- GCM
1 stop7h 10m
American Airlines
Mon 8/1712:00 pm
GCM
- ORD
2 stops9h 57m
American Airlines
Deal found 7/14![American Airlines logo]()
$671
This American Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:00 am
ORD
- GCM
1 stop8h 10m
American Airlines
Mon 8/312:10 pm
GCM
- ORD
1 stop10h 25m
American Airlines
Deal found 7/10![American Airlines logo]()
$673
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:05 am
MDW
- GCM
1 stop5h 34m
Delta
Mon 8/311:04 pm
GCM
- MDW
1 stop9h 32m
Delta
Deal found 7/12![Delta logo]()
$681
This American Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
1 stop6h 22m
American Airlines
Wed 9/22:10 pm
GCM
- ORD
1 stop8h 21m
American Airlines
Deal found 7/12![American Airlines logo]()
$670
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:41 pm
ORD
- GCM
1 stop16h 46m
American Airlines
Thu 9/312:00 pm
GCM
- ORD
1 stop11h 30m
American Airlines
Deal found 7/13![American Airlines logo]()
$672
This Orbitz deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/283:45 pm
ORD
- GCM
1 stop18h 00m
Air Canada
Mon 8/3112:25 pm
GCM
- ORD
1 stop28h 32m
Air Canada
Deal found 7/10![Air Canada logo]()
$553
This Delta deal was found by Cheapflights users on 7/14. 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 8/286:05 am
MDW
- GCM
1 stop5h 34m
Delta
Fri 9/41:04 pm
GCM
- MDW
1 stop9h 32m
Delta
Deal found 7/14![Delta logo]()
$701
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/283:15 pm
MDW
- GCM
1 stop21h 30m
Multiple Airlines
Mon 8/317:00 am
GCM
- MDW
2 stops15h 47m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$711
This Southwest deal was found by Cheapflights users on 7/15. 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.
Sat 8/295:00 am
MDW
- GCM
1 stop7h 05m
Southwest
Sat 9/51:00 pm
GCM
- MDW
1 stop7h 55m
Southwest
Deal found 7/15![Southwest logo]()
$586
This Air Canada deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/308:50 pm
ORD
- GCM
1 stop14h 35m
Air Canada
Sat 9/510:40 am
GCM
- ORD
1 stop9h 13m
Air Canada
Deal found 7/13![Air Canada logo]()
$588
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 July 15, 2026.
Search for one-way flight options from Chicago to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated July 15, 2026.
This Air Canada deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/138:50 am
ORD
- GCM
1 stop26h 35m
Air Canada
Deal found 7/11![Air Canada logo]()
$170
This Air Canada deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:05 am
ORD
- GCM
2 stops22h 40m
Air Canada
Deal found 7/11![Air Canada logo]()
$173
This Air Canada deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/91:55 pm
ORD
- GCM
2 stops21h 30m
Air Canada
Deal found 7/12![Air Canada logo]()
$175
This Air Canada deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:40 pm
ORD
- GCM
2 stops42h 05m
Air Canada
Deal found 7/12![Air Canada logo]()
$178
This Air Canada deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/78:40 pm
ORD
- GCM
1 stop14h 50m
Air Canada
Deal found 7/11![Air Canada logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:00 am
ORD
- GCM
2 stops27h 35m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$192
This Expedia deal was found by Cheapflights users on 7/15. 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 10/142:15 pm
ORD
- GCM
1 stop21h 15m
Air Canada
Deal found 7/15![Air Canada logo]()
$199
This Air Canada deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/314:30 pm
ORD
- GCM
1 stop19h 40m
Air Canada
Deal found 7/10![Air Canada logo]()
$200
This Air Canada deal was found by Cheapflights users on 7/15. 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 10/1610:40 am
ORD
- GCM
2 stops24h 50m
Air Canada
Deal found 7/15![Air Canada logo]()
$204
This Air Canada deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:40 pm
ORD
- GCM
1 stop14h 50m
Air Canada
Deal found 7/11![Air Canada logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/142:46 pm
ORD
- GCM
2 stops25h 19m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$210
This Southwest deal was found by Cheapflights users on 7/14. 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.
Sat 8/295:00 am
MDW
- GCM
1 stop7h 05m
Southwest
Deal found 7/14![Southwest logo]()
$230
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 July 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $396 (Southwest) |
One-way from | $170 (Air Canada) |
Popular in | July |
Cheapest in | October |
Average price | $853 |
Good round-trip deal | $666 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 July 15, 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
MDW - GCM
MDWGCM
Chicago Midway
Tue 11/3
5:15 am-12:35 pm
1 stop6h 20m
George Town Owen Roberts Intl
Thu 11/12
1:30 pm-6:55 pm
1 stop6h 25m
$459
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 11/21
8:50 pm-12:10 pm
1 stop14h 20m
George Town Owen Roberts Intl
Sat 11/28
1:10 pm-7:58 pm
1 stop7h 48m
$499
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Sat 8/29
5:00 am-12:05 pm
1 stop7h 05m
George Town Owen Roberts Intl
Sat 9/5
1:00 pm-8:55 pm
1 stop7h 55m
$586
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Sun 1/3
6:00 am-12:40 pm
1 stop5h 40m
George Town Owen Roberts Intl
Wed 1/13
2:05 pm-10:10 pm
1 stop9h 05m
$611
Quickest round-trip
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 1/10
5:00 am-1:15 pm
1 stop7h 15m
George Town Owen Roberts Intl
Fri 1/15
2:50 pm-6:04 pm
Nonstop4h 14m
$621
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 10/18
5:30 am-11:40 am
1 stop6h 10m
George Town Owen Roberts Intl
Fri 10/23
12:55 pm-9:00 pm
1 stop8h 05m
$631
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 11/3
7:40 am-4:30 pm
1 stop7h 50m
George Town Owen Roberts Intl
Fri 11/13
5:45 pm-7:50 am
1 stop15h 05m
$631
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 11/4
6:55 am-4:30 pm
1 stop8h 35m
George Town Owen Roberts Intl
Fri 11/13
5:45 pm-10:11 am
1 stop17h 26m
$631
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 10/25
5:30 am-11:40 am
1 stop6h 10m
George Town Owen Roberts Intl
Mon 11/2
1:55 pm-11:51 pm
1 stop10h 56m
$646
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 11/3
10:30 am-8:20 pm
2 stops8h 50m
George Town Owen Roberts Intl
Fri 11/13
3:14 pm-11:00 pm
2 stops8h 46m
$671
Showing 1-10 of 36 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 $172). Flying from Chicago to Cayman Islands in September is currently the most expensive (average of $621). 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 July 15, 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 July 15, 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.
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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
Complete your trip to Cayman Islands by adding a car rental and/or hotel reservation to your travel itinerary.
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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 July 15, 2026.
Popular flight searches
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 July 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$611 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$438 | Average$683 | FlexibilityNo cancel fee | On-time71% |