$75+ Cheap flights from Chicago (CHI) to the Cayman Islands
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
مارس 13 — مارس 201
1 adult, Economy
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Find cheap flights from Chicago to Cayman Islands with Cheapflights
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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 فبراير 11, 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 فبراير 11, 2026.
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
ح 3/19:35 pm
MDW
- GCM
2 stops14h 20m
Southwest
ث 3/1012:40 pm
GCM
- MDW
2 stops10h 10m
Southwest
Deal found 2/8![Southwest logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
ر 3/189:28 am
ORD
- GCM
2 stops27h 29m
Multiple Airlines
ر 3/2511:30 am
GCM
- ORD
1 stop20h 55m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$379
This FlightHub deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
س 3/145:05 am
ORD
- GCM
1 stop7h 15m
Spirit Airlines
خ 3/191:52 pm
GCM
- ORD
1 stop9h 25m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$380
This Air Canada deal was found by Cheapflights users on 2/10. 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.
س 4/44:15 pm
ORD
- GCM
1 stop18h 40m
Air Canada
خ 4/911:55 am
GCM
- ORD
1 stop7h 30m
Air Canada
Deal found 2/10![Air Canada logo]()
$382
This Mytrip deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
ر 3/1110:44 am
ORD
- GCM
3 stops26h 13m
Multiple Airlines
ر 3/1811:30 am
GCM
- ORD
1 stop7h 01m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
خ 3/56:15 am
MDW
- GCM
1 stop14h 00m
Multiple Airlines
خ 3/127:00 am
GCM
- MDW
1 stop6h 41m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$387
This Mytrip deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
س 2/289:18 am
ORD
- GCM
3 stops27h 25m
Multiple Airlines
ن 3/94:45 pm
GCM
- ORD
1 stop16h 54m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$391
This Mytrip deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
س 2/288:16 pm
ORD
- GCM
1 stop16h 27m
Multiple Airlines
ر 3/411:30 am
GCM
- ORD
2 stops21h 24m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
ج 5/156:31 am
ORD
- GCM
1 stop11h 29m
Multiple Airlines
ث 5/1911:30 am
GCM
- ORD
1 stop6h 45m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
ح 2/225:15 am
ORD
- GCM
1 stop7h 28m
Multiple Airlines
ر 2/2511:30 am
GCM
- ORD
1 stop23h 09m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$396
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
ن 3/164:51 pm
ORD
- GCM
1 stop23h 14m
Multiple Airlines
ج 3/208:00 am
GCM
- ORD
1 stop16h 22m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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.
ث 3/176:00 am
MDW
- GCM
2 stops10h 05m
Multiple Airlines
ن 3/237:00 am
GCM
- MDW
1 stop6h 41m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$406
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 فبراير 11, 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 فبراير 11, 2026.
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
ح 3/19:35 pm
MDW
- GCM
2 stops14h 20m
Southwest
ث 3/1012:40 pm
GCM
- MDW
1 stop6h 40m
Southwest
Deal found 2/8![Southwest logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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.
ث 3/176:00 am
MDW
- GCM
2 stops10h 05m
Multiple Airlines
ن 3/237:00 am
GCM
- MDW
1 stop6h 41m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$406
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
ح 2/226:00 am
MDW
- GCM
1 stop5h 29m
Delta
ر 2/251:54 pm
GCM
- MDW
1 stop9h 37m
Delta
Deal found 2/8![Delta logo]()
$487
This Mytrip deal was found by Cheapflights users on 2/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ر 3/186:01 pm
ORD
- GCM
3 stops18h 56m
Spirit Airlines
ح 3/221:52 pm
GCM
- ORD
2 stops21h 58m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$495
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
ن 3/168:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
ج 3/201:25 pm
GCM
- ORD
1 stop9h 48m
United Airlines
Deal found 2/8![United Airlines logo]()
$501
This American Airlines deal was found by Cheapflights users on 2/10. 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.
ن 3/99:45 am
ORD
- GCM
Nonstop3h 59m
American Airlines
خ 3/122:44 pm
GCM
- ORD
Nonstop4h 10m
American Airlines
Deal found 2/10![American Airlines logo]()
$501
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
ث 5/266:34 pm
ORD
- GCM
1 stop21h 31m
Multiple Airlines
ث 6/211:30 am
GCM
- ORD
1 stop6h 45m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$409
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
ج 4/174:10 pm
MDW
- GCM
2 stops22h 30m
Southwest
ث 4/211:05 pm
GCM
- MDW
2 stops10h 00m
Southwest
Deal found 2/9![Southwest logo]()
$464
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
ث 2/249:36 am
ORD
- GCM
Nonstop3h 59m
American Airlines
س 2/284:00 pm
GCM
- ORD
Nonstop4h 20m
American Airlines
Deal found 2/9![American Airlines logo]()
$503
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
ر 3/186:00 am
MDW
- GCM
1 stop5h 47m
Delta
ر 3/251:12 pm
GCM
- MDW
1 stop9h 19m
Delta
Deal found 2/8![Delta logo]()
$505
This Southwest deal was found by Cheapflights users on 2/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ن 4/135:35 am
MDW
- GCM
1 stop6h 35m
Southwest
س 4/181:05 pm
GCM
- MDW
1 stop9h 10m
Southwest
Deal found 2/10![Southwest logo]()
$473
This Delta deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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.
ح 4/265:10 am
ORD
- GCM
1 stop6h 50m
Delta
ر 4/291:25 pm
GCM
- ORD
1 stop6h 51m
Delta
Deal found 2/7![Delta logo]()
$505
This Mytrip deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
ح 3/86:51 pm
ORD
- GCM
3 stops26h 24m
Multiple Airlines
س 3/141:15 pm
GCM
- ORD
1 stop6h 36m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$507
This Delta deal was found by Cheapflights users on 2/10. 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.
ث 4/216:00 am
MDW
- GCM
1 stop6h 00m
Delta
ث 4/281:25 pm
GCM
- MDW
1 stop9h 03m
Delta
Deal found 2/10![Delta logo]()
$515
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
ح 3/86:05 am
MDW
- GCM
1 stop5h 55m
Southwest
س 3/1411:20 am
GCM
- MDW
1 stop8h 50m
Southwest
Deal found 2/9![Southwest logo]()
$523
This Delta deal was found by Cheapflights users on 2/10. 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.
ث 5/126:00 am
ORD
- GCM
1 stop5h 54m
Delta
ث 5/191:19 pm
GCM
- ORD
1 stop9h 09m
Delta
Deal found 2/10![Delta logo]()
$515
This Southwest deal was found by Cheapflights users on 2/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
س 4/119:20 am
MDW
- GCM
1 stop5h 20m
Southwest
خ 4/161:05 pm
GCM
- MDW
1 stop10h 35m
Southwest
Deal found 2/10![Southwest logo]()
$523
This FlightHub deal was found by Cheapflights users on 2/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ن 4/62:00 pm
ORD
- CYB
2 stops27h 50m
Multiple Airlines
ر 4/153:55 pm
CYB
- ORD
2 stops41h 15m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$630
This FlightHub deal was found by Cheapflights users on 2/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ح 4/124:15 pm
ORD
- CYB
2 stops23h 10m
Multiple Airlines
ح 4/198:30 am
CYB
- ORD
2 stops24h 40m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$630
Last-minute flights from Chicago to Cayman IslandsDiscover last-minute flight deals from Chicago to Cayman Islands. Data last updated فبراير 11, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Cayman Islands. Data last updated فبراير 11, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
ر 2/184:43 pm
ORD
- GCM
1 stop20h 00m
Multiple Airlines
ث 2/2411:30 am
GCM
- ORD
1 stop23h 09m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$392
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
ح 2/225:15 am
ORD
- GCM
1 stop7h 28m
Multiple Airlines
ر 2/2511:30 am
GCM
- ORD
1 stop23h 09m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$396
This Mytrip deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
س 2/289:18 am
ORD
- GCM
3 stops27h 25m
Multiple Airlines
ن 3/94:45 pm
GCM
- ORD
1 stop16h 54m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$391
This Mytrip deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
س 2/288:16 pm
ORD
- GCM
1 stop16h 27m
Multiple Airlines
ر 3/411:30 am
GCM
- ORD
2 stops21h 24m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$393
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
ح 3/19:35 pm
MDW
- GCM
2 stops14h 20m
Southwest
ث 3/1012:40 pm
GCM
- MDW
2 stops10h 10m
Southwest
Deal found 2/8![Southwest logo]()
$364
This Mytrip deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
ن 3/26:51 pm
ORD
- GCM
3 stops20h 14m
Multiple Airlines
خ 3/52:49 pm
GCM
- ORD
1 stop7h 24m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
خ 3/56:15 am
MDW
- GCM
1 stop14h 00m
Multiple Airlines
خ 3/127:00 am
GCM
- MDW
1 stop6h 41m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$387
This Mytrip deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
ر 3/1110:44 am
ORD
- GCM
3 stops26h 13m
Multiple Airlines
ر 3/1811:30 am
GCM
- ORD
1 stop7h 01m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$385
This FlightHub deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
س 3/145:05 am
ORD
- GCM
1 stop7h 15m
Spirit Airlines
خ 3/191:52 pm
GCM
- ORD
1 stop9h 25m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$380
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
ن 3/164:51 pm
ORD
- GCM
1 stop23h 14m
Multiple Airlines
ج 3/208:00 am
GCM
- ORD
1 stop16h 22m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
ر 3/189:28 am
ORD
- GCM
2 stops27h 29m
Multiple Airlines
ر 3/2511:30 am
GCM
- ORD
1 stop20h 55m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$379
This FlightHub deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ن 3/307:04 am
ORD
- GCM
1 stop28h 06m
Air Canada
ن 4/611:25 am
GCM
- ORD
1 stop25h 40m
Air Canada
Deal found 2/8![Air Canada logo]()
$382
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 فبراير 11, 2026.
Search for one-way flight options from Chicago to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated فبراير 11, 2026.
This FlightHub deal was found by Cheapflights users on 2/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
س 4/115:05 am
ORD
- GCM
1 stop7h 15m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$75
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
ر 5/61:27 pm
ORD
- GCM
1 stop23h 16m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$86
This FlightHub deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
خ 3/55:15 am
ORD
- GCM
1 stop7h 28m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
ر 3/116:36 pm
ORD
- GCM
1 stop18h 21m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
ر 4/86:10 pm
ORD
- GCM
1 stop18h 47m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
ر 3/48:16 pm
ORD
- GCM
1 stop16h 27m
Spirit Airlines
Deal found 2/8![Spirit Airlines logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
ج 4/107:17 am
ORD
- GCM
1 stop29h 03m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$99
This FlightHub deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
س 3/78:16 pm
ORD
- GCM
1 stop15h 27m
Spirit Airlines
Deal found 2/8![Spirit Airlines logo]()
$102
This Trip.com deal was found by Cheapflights users on 2/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
س 5/93:52 pm
ORD
- GCM
1 stop19h 43m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$108
This FlightHub deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
خ 5/75:15 am
ORD
- GCM
1 stop7h 28m
Spirit Airlines
Deal found 2/7![Spirit Airlines logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
خ 3/125:05 am
ORD
- GCM
1 stop7h 52m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$117
This Southwest deal was found by Cheapflights users on 2/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ح 4/127:20 pm
MDW
- GCM
2 stops16h 50m
Southwest
Deal found 2/10![Southwest logo]()
$127
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 فبراير 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $364 (Southwest) |
One-way from | $75 (FlightHub) |
Popular in | December |
Cheapest in | February |
Average price | $527 |
Good round-trip deal | $500 or less |
Good one-way deal | $288 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 فبراير 11, 2026.
Use the filters below to find and compare flights from Chicago to the Cayman Islands that are best for you.
Fly from
Chicago
Fly to
Cayman Islands
Route
Depart
Return
Price
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
ح 3/1
9:35 pm-12:55 pm
2 stops14h 20m
George Town Owen Roberts Intl
ث 3/10
12:40 pm-7:20 pm
1 stop6h 40m
$364
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
ث 3/17
6:00 am-4:05 pm
2 stops10h 05m
George Town Owen Roberts Intl
ن 3/23
7:00 am-1:41 pm
1 stop6h 41m
$406
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
ث 5/26
6:34 pm-4:05 pm
1 stop21h 31m
George Town Owen Roberts Intl
ث 6/2
11:30 am-6:15 pm
1 stop6h 45m
$409
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
ج 4/17
4:10 pm-2:40 pm
2 stops22h 30m
George Town Owen Roberts Intl
ث 4/21
1:05 pm-11:05 pm
2 stops10h 00m
$464
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
ن 4/13
5:35 am-12:10 pm
1 stop6h 35m
George Town Owen Roberts Intl
س 4/18
1:05 pm-10:15 pm
1 stop9h 10m
$473
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
ح 2/22
6:00 am-12:29 pm
1 stop5h 29m
George Town Owen Roberts Intl
ر 2/25
1:54 pm-10:31 pm
1 stop9h 37m
$487
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
ر 3/18
6:01 pm-12:57 pm
3 stops18h 56m
George Town Owen Roberts Intl
ح 3/22
1:52 pm-11:50 am
2 stops21h 58m
$495
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
ن 3/16
8:45 am-12:45 pm
Nonstop4h 00m
George Town Owen Roberts Intl
ج 3/20
1:25 pm-11:13 pm
1 stop9h 48m
$501
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
ن 3/9
9:45 am-1:44 pm
Nonstop3h 59m
George Town Owen Roberts Intl
خ 3/12
2:44 pm-6:54 pm
Nonstop4h 10m
$501
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
ث 2/24
9:36 am-2:35 pm
Nonstop3h 59m
George Town Owen Roberts Intl
س 2/28
4:00 pm-7:20 pm
Nonstop4h 20m
$503
Showing 1-10 of 33 results
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, December is the cheapest month in which you can book a flight from Chicago to Cayman Islands (average of $322). Flying from Chicago to Cayman Islands in September is currently the most expensive (average of $659). 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 فبراير 11, 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 فبراير 11, 2026.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Chicago to the Cayman Islands. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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 فبراير 11, 2026.
Popular flight searches
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Fly to Cayman Islands regions
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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 فبراير 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$617 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$438 | Average$677 | FlexibilityNo cancel fee | On-time71% |