$154+ Cheap flights from Chicago (CHI) to the Cayman Islands
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Nov 25 — Dec 21
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 October 26, 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 October 26, 2026.
This Trip.com deal was found by Cheapflights users on 10/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:30 pm -
1 stop18h 40m
Tue 12/81:10 pm -
1 stop20h 58m
Deal found 10/23![Air Canada logo]()
$394
This Trip.com deal was found by Cheapflights users on 10/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2410:15 am -
1 stop24h 55m
Tue 12/11:10 pm -
1 stop20h 58m
Deal found 10/26![Air Canada logo]()
$405
This CheapOair deal was found by Cheapflights users on 10/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:17 pm -
1 stop16h 53m
Thu 12/171:10 pm -
1 stop7h 48m
Deal found 10/25![Air Canada logo]()
$419
This Trip.com deal was found by Cheapflights users on 10/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:15 am -
1 stop24h 55m
Fri 11/61:10 pm -
1 stop21h 13m
Deal found 10/23![Air Canada logo]()
$421
This Travelocity deal was found by Cheapflights users on 10/23. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:50 pm -
1 stop22h 20m
Sun 11/11:10 pm -
1 stop29h 33m
Deal found 10/23![Air Canada logo]()
$429
This Justfly.com deal was found by Cheapflights users on 10/24. 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 Justfly.com is selected, and click “Compare selected ” under the list of providers to see comparable flight deals.
Wed 12/26:17 pm -
1 stop16h 53m
Wed 12/91:10 pm -
1 stop7h 48m
Deal found 10/24![Air Canada logo]()
$438
This Air Canada deal was found by Cheapflights users on 10/23. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/211:05 am -
1 stop24h 05m
Fri 12/111:10 pm -
1 stop7h 48m
Deal found 10/23![Air Canada logo]()
$439
This Expedia deal was found by Cheapflights users on 10/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2810:37 am -
2 stops48h 33m
Sun 11/11:10 pm -
2 stops43h 50m
Deal found 10/23![Air Canada logo]()
$442
This Trip.com deal was found by Cheapflights users on 10/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1012:50 pm -
1 stop22h 20m
Sun 12/131:10 pm -
1 stop27h 28m
Deal found 10/22![Air Canada logo]()
$457
This Southwest deal was found by Cheapflights users on 10/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/85:20 am -
1 stop6h 15m
Tue 12/151:30 pm -
1 stop7h 05m
Deal found 10/24![Southwest logo]()
$510
This Southwest deal was found by Cheapflights users on 10/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/135:10 am -
1 stop6h 25m
Thu 12/171:30 pm -
1 stop6h 25m
Deal found 10/25![Southwest logo]()
$564
This Southwest deal was found by Cheapflights users on 10/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/28:50 pm -
2 stops14h 45m
Sat 12/51:55 pm -
2 stops16h 45m
Deal found 10/23![Southwest logo]()
$583
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 October 26, 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 October 26, 2026.
This Southwest deal was found by Cheapflights users on 10/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/85:20 am -
1 stop6h 15m
Tue 12/151:30 pm -
1 stop7h 05m
Deal found 10/24![Southwest logo]()
$510
This United Airlines deal was found by Cheapflights users on 10/22. 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 2/67:25 am -
1 stop7h 35m
Thu 2/112:55 pm -
Nonstop4h 18m
Deal found 10/22![United Airlines logo]()
$647
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/246:00 am -
1 stop6h 12m
Thu 12/313:51 pm -
1 stop8h 16m
Deal found 10/25![Delta logo]()
$678
This Southwest deal was found by Cheapflights users on 10/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/56:15 pm -
2 stops17h 55m
Fri 4/91:05 pm -
2 stops9h 45m
Deal found 10/23![Southwest logo]()
$558
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/78:42 am -
Nonstop4h 03m
Thu 1/142:25 pm -
1 stop8h 45m
Deal found 10/22![United Airlines logo]()
$671
This Delta deal was found by Cheapflights users on 10/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/246:00 am -
1 stop6h 12m
Thu 12/313:51 pm -
1 stop7h 31m
Deal found 10/24![Delta logo]()
$678
This United Airlines deal was found by Cheapflights users on 10/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/148:42 am -
Nonstop4h 03m
Sun 2/215:45 pm -
1 stop8h 00m
Deal found 10/25![United Airlines logo]()
$673
This Southwest deal was found by Cheapflights users on 10/21. 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 2/256:55 pm -
2 stops17h 00m
Sun 2/281:50 pm -
1 stop10h 30m
Deal found 10/21![Southwest logo]()
$712
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/256:00 am -
1 stop5h 40m
Tue 3/22:05 pm -
1 stop9h 05m
Deal found 10/25![Delta logo]()
$720
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/186:00 am -
1 stop9h 30m
Thu 3/254:45 pm -
1 stop7h 55m
Deal found 10/22![United Airlines logo]()
$687
This Southwest deal was found by Cheapflights users on 10/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/145:25 am -
1 stop6h 30m
Sun 2/211:50 pm -
2 stops11h 05m
Deal found 10/25![Southwest logo]()
$752
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/105:30 am -
1 stop6h 44m
Wed 1/132:39 pm -
1 stop8h 41m
Deal found 10/25![Delta logo]()
$754
This United Airlines deal was found by Cheapflights users on 10/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/38:42 am -
Nonstop4h 03m
Wed 1/132:55 pm -
Nonstop4h 18m
Deal found 10/23![United Airlines logo]()
$753
This Southwest deal was found by Cheapflights users on 10/21. 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 2/256:15 am -
1 stop5h 40m
Mon 3/11:50 pm -
2 stops11h 05m
Deal found 10/21![Southwest logo]()
$762
This Delta deal was found by Cheapflights users on 10/26. 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.
Tue 11/246:00 am -
1 stop5h 25m
Tue 12/11:40 pm -
1 stop10h 14m
Deal found 10/26![Delta logo]()
$765
This Southwest deal was found by Cheapflights users on 10/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/245:25 am -
1 stop6h 10m
Tue 12/11:30 pm -
2 stops10h 15m
Deal found 10/26![Southwest logo]()
$762
This Delta deal was found by Cheapflights users on 10/26. 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.
Wed 3/176:00 am -
1 stop5h 45m
Tue 3/231:10 pm -
1 stop9h 00m
Deal found 10/26![Delta logo]()
$765
This United Airlines deal was found by Cheapflights users on 10/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/58:42 am -
Nonstop4h 03m
Thu 12/105:45 pm -
1 stop16h 26m
Deal found 10/24![United Airlines logo]()
$803
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/78:42 am -
Nonstop4h 03m
Mon 1/112:55 pm -
Nonstop4h 18m
Deal found 10/21![United Airlines logo]()
$813
Last-minute flights from Chicago to Cayman IslandsDiscover last-minute flight deals from Chicago to Cayman Islands. Data last updated October 26, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Cayman Islands. Data last updated October 26, 2026 and is based on user searches.
This Travelocity deal was found by Cheapflights users on 10/23. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:50 pm -
1 stop22h 20m
Sun 11/11:10 pm -
1 stop29h 33m
Deal found 10/23![Air Canada logo]()
$429
This Orbitz deal was found by Cheapflights users on 10/23. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:05 am -
2 stops52h 05m
Sun 11/11:10 pm -
1 stop29h 33m
Deal found 10/23![Air Canada logo]()
$432
This Trip.com deal was found by Cheapflights users on 10/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:15 am -
1 stop24h 55m
Fri 11/61:10 pm -
1 stop21h 13m
Deal found 10/23![Air Canada logo]()
$421
This Air Canada deal was found by Cheapflights users on 10/25. 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.
Sat 11/73:40 pm -
2 stops19h 30m
Wed 11/111:10 pm -
1 stop21h 13m
Deal found 10/25![Air Canada logo]()
$482
This Southwest deal was found by Cheapflights users on 10/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/85:10 am -
1 stop6h 25m
Thu 11/121:30 pm -
1 stop8h 05m
Deal found 10/24![Southwest logo]()
$738
This Trip.com deal was found by Cheapflights users on 10/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/144:30 pm -
1 stop18h 40m
Sat 11/211:10 pm -
1 stop21h 13m
Deal found 10/22![Air Canada logo]()
$473
This Southwest deal was found by Cheapflights users on 10/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:25 pm -
2 stops17h 10m
Sat 11/212:20 pm -
2 stops9h 45m
Deal found 10/25![Southwest logo]()
$682
This Southwest deal was found by Cheapflights users on 10/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/209:25 pm -
2 stops15h 00m
Wed 11/251:30 pm -
2 stops10h 30m
Deal found 10/24![Southwest logo]()
$674
This Trip.com deal was found by Cheapflights users on 10/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2410:15 am -
1 stop24h 55m
Tue 12/11:10 pm -
1 stop20h 58m
Deal found 10/26![Air Canada logo]()
$405
This Southwest deal was found by Cheapflights users on 10/22. 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 11/286:35 am -
1 stop5h 50m
Sat 12/51:55 pm -
1 stop7h 30m
Deal found 10/22![Southwest logo]()
$648
This Air Canada deal was found by Cheapflights users on 10/24. 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.
Mon 11/3010:57 am -
2 stops24h 13m
Fri 12/111:10 pm -
1 stop7h 48m
Deal found 10/24![Air Canada logo]()
$439
This Air Canada deal was found by Cheapflights users on 10/24. 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.
Mon 11/309:21 pm -
1 stop13h 49m
Sun 12/61:10 pm -
1 stop7h 48m
Deal found 10/24![Air Canada logo]()
$489
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 October 26, 2026.
Search for one-way flight options from Chicago to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated October 26, 2026.
This Trip.com deal was found by Cheapflights users on 10/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:50 pm -
1 stop22h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Air Canada logo]()
$154
This Flightnetwork deal was found by Cheapflights users on 10/26. 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.
Mon 11/1610:15 am -
1 stop24h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Air Canada logo]()
$157
This Orbitz deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:45 am -
1 stop26h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Air Canada logo]()
$165
This Air Canada deal was found by Cheapflights users on 10/22. 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 12/61:55 pm -
2 stops21h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Air Canada logo]()
$168
This Southwest deal was found by Cheapflights users on 10/22. 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 12/66:05 pm -
2 stops17h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/410:38 am -
2 stops50h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/265:55 pm -
2 stops40h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$221
This Mytrip deal was found by Cheapflights users on 10/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:17 am -
2 stops11h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/510:40 am -
3 stops50h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$240
This Air Canada deal was found by Cheapflights users on 10/25. 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.
Sat 10/314:30 pm -
1 stop19h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Air Canada logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/510:00 am -
3 stops48h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/410:41 am -
3 stops50h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$255
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 October 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $394 (Trip.com) |
One-way from | $154 (Trip.com) |
Popular in | July |
Cheapest in | February |
Average price | $726 |
Good round-trip deal | $672 or less |
Good one-way deal | $328 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 7,457,451 searches. Data last updated October 26, 2026.
Use the filters below to find and compare flights from Chicago to the Cayman Islands that are best for you.
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Cheapest round-trip
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Mon 11/16
10:15 am-12:10 pm
1 stop24h 55m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$157
ChicagoGeorge Town
MDW Chicago Midway - GCM George Town Owen Roberts Intl
MDWGCM
Chicago Midway
Sun 12/6
6:05 pm-12:35 pm
2 stops17h 30m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$169
ChicagoGeorge Town
MDW Chicago Midway - GCM George Town Owen Roberts Intl
MDWGCM
Chicago Midway
Sat 12/5
10:40 am-2:35 pm
3 stops50h 55m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$240
ChicagoGeorge Town
MDW Chicago Midway - GCM George Town Owen Roberts Intl
MDWGCM
Chicago Midway
Sun 12/6
5:02 pm-11:35 am
3 stops17h 33m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$259
ChicagoGeorge Town
MDW Chicago Midway - GCM George Town Owen Roberts Intl
MDWGCM
Chicago Midway
Thu 12/3
8:50 pm-12:35 pm
2 stops14h 45m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$271
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Wed 11/18
8:45 am-12:10 pm
1 stop26h 25m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$290
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Sun 11/15
7:55 am-5:20 pm
3 stops32h 25m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$292
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Tue 12/22
8:05 am-2:36 pm
1 stop5h 31m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$300
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Wed 12/23
6:25 am-1:12 pm
1 stop5h 47m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$300
ChicagoGeorge Town
MDW Chicago Midway - GCM George Town Owen Roberts Intl
MDWGCM
Chicago Midway
Fri 11/6
5:10 am-12:35 pm
1 stop6h 25m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$301
Showing 1-10 of 37 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.
MDW-GCM
ORD-GCM
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
MDW-GCM
ORD-GCM
What is the cheapest month to book a flight from Chicago to Cayman Islands?
Currently, February is the cheapest month in which you can book a flight from Chicago to Cayman Islands (average of $592). Flying from Chicago to Cayman Islands in July is currently the most expensive (average of $806). 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.
How far ahead should I book a flight from Chicago to Cayman Islands?
To ensure you get the cheapest price possible for a flight from Chicago to Cayman Islands, you should look to book at least 1 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
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 October 26, 2026.
Read reviews from past customers who have flown Delta,United Airlines, andAmerican 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.
Entertainment
7.8
Boarding
8.1
Overall
7.8
Food
7.2
Comfort
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Entertainment
7.8
Boarding
8.1
Overall
7.8
Food
7.2
Comfort
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Entertainment
7.8
Boarding
8.1
Overall
7.8
Food
7.2
Comfort
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Entertainment
7.8
Boarding
8.1
Overall
7.8
Food
7.2
Comfort
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
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.
Search flights from Chicago to Cayman Islands by cabin class
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 October 26, 2026.
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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 7,457,451 searches. Data last updated October 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$344 | Average$660 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$447 | Average$704 | FlexibilityNo cancel fee | On-time71% |