$131+ 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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Sep 30 — Oct 71
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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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 August 31, 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 August 31, 2026.
This Vliegwinkel deal was found by Cheapflights users on 8/30. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:45 pm -
1 stop18h 00m
Thu 9/1712:25 pm -
1 stop20h 35m
Deal found 8/30![Air Canada logo]()
$301
This Trip.com deal was found by Cheapflights users on 8/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:05 am -
1 stop25h 05m
Wed 12/91:10 pm -
1 stop20h 58m
Deal found 8/30![Air Canada logo]()
$334
This Air Canada deal was found by Cheapflights users on 8/29. 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.
Fri 9/118:40 pm -
1 stop13h 05m
Thu 9/2412:25 pm -
1 stop20h 35m
Deal found 8/29![Air Canada logo]()
$361
This Expedia deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:40 pm -
1 stop14h 30m
Sat 10/3112:10 pm -
1 stop8h 03m
Deal found 8/26![Air Canada logo]()
$369
This Air Canada deal was found by Cheapflights users on 8/30. 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.
Fri 9/181:55 pm -
2 stops19h 50m
Thu 9/2412:25 pm -
1 stop26h 30m
Deal found 8/30![Air Canada logo]()
$371
This Flightnetwork deal was found by Cheapflights users on 8/28. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:35 pm -
1 stop16h 55m
Thu 10/2212:25 pm -
1 stop20h 35m
Deal found 8/28![Air Canada logo]()
$373
This Expedia deal was found by Cheapflights users on 8/27. 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.
Wed 11/187:05 am -
2 stops28h 05m
Tue 11/241:10 pm -
2 stops26h 42m
Deal found 8/27![Air Canada logo]()
$376
This Southwest deal was found by Cheapflights users on 8/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:20 am -
1 stop6h 15m
Wed 12/91:30 pm -
1 stop7h 00m
Deal found 8/30![Southwest logo]()
$478
This Southwest deal was found by Cheapflights users on 8/26. 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.
Fri 10/306:25 pm -
2 stops17h 45m
Tue 11/31:30 pm -
2 stops10h 05m
Deal found 8/26![Southwest logo]()
$479
This Southwest deal was found by Cheapflights users on 8/29. 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.
Thu 12/108:50 pm -
2 stops14h 45m
Mon 12/141:30 pm -
2 stops10h 10m
Deal found 8/29![Southwest logo]()
$532
This Southwest deal was found by Cheapflights users on 8/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/315:20 am -
1 stop6h 15m
Thu 1/211:50 pm -
2 stops10h 10m
Deal found 8/30![Southwest logo]()
$583
This Delta deal was found by Cheapflights users on 8/30. 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.
Mon 12/286:15 pm -
1 stop16h 30m
Fri 1/222:05 pm -
1 stop9h 05m
Deal found 8/30![Delta logo]()
$631
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 August 31, 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 August 31, 2026.
This Southwest deal was found by Cheapflights users on 8/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:25 pm -
2 stops17h 45m
Tue 11/31:30 pm -
2 stops10h 05m
Deal found 8/28![Southwest logo]()
$483
This Air Canada deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/43:45 pm -
2 stops19h 25m
Fri 2/121:10 pm -
2 stops19h 48m
Deal found 8/26![Air Canada logo]()
$550
This United Airlines deal was found by Cheapflights users on 8/27. 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 1/37:00 am -
1 stop8h 05m
Wed 1/132:55 pm -
Nonstop4h 18m
Deal found 8/27![United Airlines logo]()
$621
This Delta deal was found by Cheapflights users on 8/28. 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.
Sun 1/247:55 pm -
1 stop15h 45m
Wed 2/32:05 pm -
1 stop8h 05m
Deal found 8/28![Delta logo]()
$631
This Expedia deal was found by Cheapflights users on 8/27. 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.
Sun 10/118:40 pm -
2 stops21h 10m
Sun 10/186:20 pm -
2 stops44h 35m
Deal found 8/27![Multiple Airlines logo]()
$729
This Air Canada deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:30 pm -
1 stop18h 40m
Sat 12/191:10 pm -
1 stop20h 58m
Deal found 8/26![Air Canada logo]()
$628
This United Airlines deal was found by Cheapflights users on 8/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/48:45 am -
Nonstop4h 00m
Fri 2/122:50 pm -
Nonstop4h 14m
Deal found 8/26![United Airlines logo]()
$642
This Southwest deal was found by Cheapflights users on 8/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:05 pm -
2 stops17h 30m
Sun 11/151:30 pm -
2 stops10h 35m
Deal found 8/27![Southwest logo]()
$648
This Delta deal was found by Cheapflights users on 8/30. 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 1/205:30 am -
1 stop6h 10m
Mon 1/252:05 pm -
1 stop8h 05m
Deal found 8/30![Delta logo]()
$656
This United Airlines deal was found by Cheapflights users on 8/30. 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 1/308:42 am -
Nonstop4h 03m
Wed 2/32:55 pm -
Nonstop4h 18m
Deal found 8/30![United Airlines logo]()
$642
This Air Canada deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/211:55 pm -
2 stops21h 15m
Sun 2/281:10 pm -
1 stop7h 48m
Deal found 8/26![Air Canada logo]()
$656
This Delta deal was found by Cheapflights users on 8/28. 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 1/235:45 pm -
2 stops17h 55m
Tue 2/22:05 pm -
2 stops23h 32m
Deal found 8/28![Delta logo]()
$661
This United Airlines deal was found by Cheapflights users on 8/27. 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.
Sat 10/318:42 am -
Nonstop4h 03m
Sat 11/72:55 pm -
Nonstop4h 18m
Deal found 8/27![United Airlines logo]()
$667
This Delta deal was found by Cheapflights users on 8/30. 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.
Sat 11/146:00 am -
1 stop5h 43m
Sat 11/212:08 pm -
1 stop9h 46m
Deal found 8/30![Delta logo]()
$681
This United Airlines deal was found by Cheapflights users on 8/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:52 pm -
1 stop16h 23m
Sat 10/311:55 pm -
Nonstop4h 18m
Deal found 8/26![United Airlines logo]()
$671
This Southwest deal was found by Cheapflights users on 8/26. 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.
Sat 10/105:00 am -
1 stop7h 10m
Sat 10/171:05 pm -
1 stop8h 10m
Deal found 8/26![Southwest logo]()
$903
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:05 am -
1 stop5h 35m
Thu 9/171:00 pm -
2 stops20h 07m
Deal found 8/28![Delta logo]()
$853
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:04 am -
1 stop5h 36m
Thu 10/2212:55 pm -
1 stop9h 38m
Deal found 8/28![Delta logo]()
$906
This Delta deal was found by Cheapflights users on 8/27. 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 10/106:04 am -
1 stop5h 36m
Sat 10/171:05 pm -
1 stop9h 28m
Deal found 8/27![Delta logo]()
$1,011
This Delta deal was found by Cheapflights users on 8/30. 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.
Sat 11/286:00 am -
1 stop5h 43m
Sat 12/52:08 pm -
1 stop9h 47m
Deal found 8/30![Delta logo]()
$1,011
Last-minute flights from Chicago to Cayman IslandsDiscover last-minute flight deals from Chicago to Cayman Islands. Data last updated August 31, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Cayman Islands. Data last updated August 31, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:00 pm -
2 stops17h 05m
Sun 12/201:30 pm -
1 stop8h 15m
Deal found 8/30![Southwest logo]()
$669
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Fri 9/43:20 pm -
1 stop21h 25m
Tue 9/811:30 am -
2 stops30h 21m
Deal found 8/28![Multiple Airlines logo]()
$856
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:05 am -
1 stop5h 34m
Fri 9/111:00 pm -
1 stop9h 44m
Deal found 8/28![Delta logo]()
$921
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Fri 9/411:45 am -
1 stop25h 00m
Wed 9/911:30 am -
2 stops30h 16m
Deal found 8/28![Multiple Airlines logo]()
$927
This Vliegwinkel deal was found by Cheapflights users on 8/30. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:45 pm -
1 stop18h 00m
Thu 9/1712:25 pm -
1 stop20h 35m
Deal found 8/30![Air Canada logo]()
$301
This Air Canada deal was found by Cheapflights users on 8/29. 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.
Fri 9/118:40 pm -
1 stop13h 05m
Thu 9/2412:25 pm -
1 stop20h 35m
Deal found 8/29![Air Canada logo]()
$361
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:05 am -
1 stop5h 35m
Thu 9/171:00 pm -
2 stops20h 07m
Deal found 8/28![Delta logo]()
$853
This Delta deal was found by Cheapflights users on 8/27. 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.
Fri 9/116:05 am -
1 stop5h 35m
Thu 9/241:00 pm -
1 stop9h 44m
Deal found 8/27![Delta logo]()
$876
This Expedia deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/133:45 pm -
1 stop19h 40m
Sat 9/1910:40 am -
1 stop26h 43m
Deal found 8/26![Air Canada logo]()
$406
This Air Canada deal was found by Cheapflights users on 8/30. 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.
Fri 9/181:55 pm -
2 stops19h 50m
Thu 9/2412:25 pm -
1 stop26h 30m
Deal found 8/30![Air Canada logo]()
$371
This Delta deal was found by Cheapflights users on 8/26. 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.
Thu 9/246:05 am -
1 stop5h 35m
Thu 10/11:00 pm -
1 stop9h 44m
Deal found 8/26![Delta logo]()
$771
This Delta deal was found by Cheapflights users on 8/28. 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.
Sun 9/276:05 am -
1 stop5h 35m
Sun 10/41:00 pm -
1 stop9h 44m
Deal found 8/28![Delta logo]()
$786
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 August 31, 2026.
Search for one-way flight options from Chicago to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated August 31, 2026.
This Expedia deal was found by Cheapflights users on 8/28. 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 9/273:45 pm -
1 stop19h 40m
Deal found 8/28![Air Canada logo]()
$131
This Travelocity deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2710:15 am -
1 stop24h 55m
Deal found 8/27![Air Canada logo]()
$135
This Travelocity deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:45 am -
2 stops49h 45m
Deal found 8/27![Air Canada logo]()
$138
This Air Canada deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/263:40 pm -
2 stops43h 45m
Deal found 8/28![Air Canada logo]()
$139
This Air Canada deal was found by Cheapflights users on 8/31. 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 11/184:30 pm -
1 stop18h 40m
Deal found 8/31![Air Canada logo]()
$145
This Air Canada deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:55 pm -
2 stops21h 15m
Deal found 8/27![Air Canada logo]()
$153
This Air Canada deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/118:40 pm -
1 stop14h 45m
Deal found 8/27![Air Canada logo]()
$155
This Southwest deal was found by Cheapflights users on 8/26. 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.
Sat 10/105:00 am -
1 stop7h 10m
Deal found 8/26![Southwest logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:21 am -
2 stops29h 14m
Deal found 8/26![Multiple Airlines logo]()
$258
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:00 am -
1 stop5h 25m
Deal found 8/27![Delta logo]()
$308
This Delta deal was found by Cheapflights users on 8/27. 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 10/316:04 am -
1 stop5h 36m
Deal found 8/27![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 8/27. 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 10/116:04 am -
1 stop5h 36m
Deal found 8/27![Delta logo]()
$763
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 August 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $301 (Vliegwinkel) |
One-way from | $131 (Expedia) |
Popular in | July |
Cheapest in | February |
Average price | $691 |
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 7,457,451 searches. Data last updated August 31, 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 Chicago Midway - GCM George Town Owen Roberts Intl
MDWGCM
Chicago Midway
Fri 10/30
6:25 pm-12:10 pm
2 stops17h 45m
George Town Owen Roberts Intl
Tue 11/3
1:30 pm-10:35 pm
2 stops10h 05m
$483
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Thu 2/4
3:45 pm-12:10 pm
2 stops19h 25m
George Town Owen Roberts Intl
Fri 2/12
1:10 pm-7:58 am
2 stops19h 48m
$550
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Sun 1/3
7:00 am-4:05 pm
1 stop8h 05m
George Town Owen Roberts Intl
Wed 1/13
2:55 pm-6:13 pm
Nonstop4h 18m
$621
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Sat 12/5
4:30 pm-12:10 pm
1 stop18h 40m
George Town Owen Roberts Intl
Sat 12/19
1:10 pm-9:08 am
1 stop20h 58m
$628
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Sun 1/24
7:55 pm-12:40 pm
1 stop15h 45m
George Town Owen Roberts Intl
Wed 2/3
2:05 pm-9:10 pm
1 stop8h 05m
$631
Quickest round-trip
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Thu 2/4
8:45 am-1:45 pm
Nonstop4h 00m
George Town Owen Roberts Intl
Fri 2/12
2:50 pm-6:04 pm
Nonstop4h 14m
$642
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Sat 1/30
8:42 am-1:45 pm
Nonstop4h 03m
George Town Owen Roberts Intl
Wed 2/3
2:55 pm-6:13 pm
Nonstop4h 18m
$642
ChicagoGeorge Town
MDW Chicago Midway - GCM George Town Owen Roberts Intl
MDWGCM
Chicago Midway
Thu 11/12
6:05 pm-12:35 pm
2 stops17h 30m
George Town Owen Roberts Intl
Sun 11/15
1:30 pm-11:05 pm
2 stops10h 35m
$648
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Wed 1/20
5:30 am-12:40 pm
1 stop6h 10m
George Town Owen Roberts Intl
Mon 1/25
2:05 pm-9:10 pm
1 stop8h 05m
$656
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Sun 2/21
1:55 pm-12:10 pm
2 stops21h 15m
George Town Owen Roberts Intl
Sun 2/28
1:10 pm-7:58 pm
1 stop7h 48m
$656
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.
MDW-GCM
ORD-GCM
ORD-CYB
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to the Cayman Islands
CHI-KY0
MDW-GCM
ORD-GCM
ORD-CYB
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 $539). Flying from Chicago to Cayman Islands in November is currently the most expensive (average of $873). 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 August 31, 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.
Food
7.2
Entertainment
7.8
Comfort
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Food
7.2
Entertainment
7.8
Comfort
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Food
7.2
Entertainment
7.8
Comfort
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Food
7.2
Entertainment
7.8
Comfort
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - 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 August 31, 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 7,457,451 searches. Data last updated August 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$625 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$438 | Average$705 | FlexibilityNo cancel fee | On-time71% |