$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 6/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Jun 29 — Jul 61
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 May 30, 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 May 30, 2026.
This Expedia deal was found by Cheapflights users on 5/26. 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 6/79:55 am
ORD
- GCM
1 stop25h 30m
Air Canada
Thu 6/1112:25 pm
GCM
- ORD
1 stop26h 30m
Air Canada
Deal found 5/26![Air Canada logo]()
$361
This FlightHub deal was found by Cheapflights users on 5/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/32:15 pm
ORD
- GCM
1 stop21h 10m
Air Canada
Sat 6/610:55 am
GCM
- ORD
1 stop7h 56m
Air Canada
Deal found 5/28![Air Canada logo]()
$385
This Air Canada deal was found by Cheapflights users on 5/25. 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.
Sun 6/79:55 am
ORD
- GCM
1 stop25h 30m
Air Canada
Mon 6/1512:25 pm
GCM
- ORD
1 stop25h 00m
Air Canada
Deal found 5/25![Air Canada logo]()
$387
This Air Canada deal was found by Cheapflights users on 5/29. 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 6/122:00 pm
ORD
- GCM
1 stop20h 00m
Air Canada
Mon 6/2212:25 pm
GCM
- ORD
1 stop24h 57m
Air Canada
Deal found 5/29![Air Canada logo]()
$411
This Air Canada deal was found by Cheapflights users on 5/29. 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.
Wed 9/235:35 pm
ORD
- GCM
1 stop17h 55m
Air Canada
Sat 9/2612:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 5/29![Air Canada logo]()
$415
This Expedia deal was found by Cheapflights users on 5/27. 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.
Sat 9/123:40 pm
ORD
- GCM
2 stops43h 50m
Air Canada
Sat 9/1912:25 pm
GCM
- ORD
1 stop24h 58m
Air Canada
Deal found 5/27![Air Canada logo]()
$418
This Travelocity deal was found by Cheapflights users on 5/27. 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.
Sat 10/173:40 pm
ORD
- GCM
2 stops43h 50m
Air Canada
Sat 10/2412:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 5/27![Air Canada logo]()
$420
This Expedia deal was found by Cheapflights users on 5/27. 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.
Thu 9/38:45 am
ORD
- GCM
2 stops49h 00m
Air Canada
Mon 9/712:25 pm
GCM
- ORD
1 stop26h 30m
Air Canada
Deal found 5/27![Air Canada logo]()
$442
This Orbitz deal was found by Cheapflights users on 5/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/31:55 pm
ORD
- GCM
2 stops45h 35m
Air Canada
Sat 10/1012:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 5/29![Air Canada logo]()
$445
This FlightHub deal was found by Cheapflights users on 5/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:35 pm
ORD
- GCM
1 stop17h 55m
Air Canada
Sat 9/1912:25 pm
GCM
- ORD
1 stop19h 35m
Air Canada
Deal found 5/27![Air Canada logo]()
$454
This Southwest deal was found by Cheapflights users on 5/29. 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.
Fri 11/135:10 am
MDW
- GCM
1 stop6h 25m
Southwest
Mon 11/161:30 pm
GCM
- MDW
2 stops10h 10m
Southwest
Deal found 5/29![Southwest logo]()
$480
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/165:10 am
MDW
- GCM
1 stop6h 45m
Southwest
Sat 6/201:05 pm
GCM
- MDW
1 stop9h 20m
Southwest
Deal found 5/29![Southwest logo]()
$514
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 May 30, 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 May 30, 2026.
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/167:35 pm
MDW
- GCM
2 stops16h 20m
Southwest
Sat 6/201:05 pm
GCM
- MDW
1 stop9h 20m
Southwest
Deal found 5/29![Southwest logo]()
$519
This Delta deal was found by Cheapflights users on 5/27. 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 9/95:30 am
ORD
- GCM
1 stop6h 11m
Delta
Fri 9/1812:55 pm
GCM
- ORD
2 stops19h 07m
Delta
Deal found 5/27![Delta logo]()
$616
This American Airlines deal was found by Cheapflights users on 5/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:50 pm
ORD
- GCM
1 stop16h 40m
American Airlines
Sat 9/1211:55 am
GCM
- ORD
2 stops11h 55m
American Airlines
Deal found 5/26![American Airlines logo]()
$651
This United Airlines deal was found by Cheapflights users on 5/26. 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.
Fri 11/137:45 am
ORD
- GCM
1 stop7h 45m
United Airlines
Sat 11/212:50 pm
GCM
- ORD
Nonstop4h 14m
United Airlines
Deal found 5/26![United Airlines logo]()
$671
This Mytrip deal was found by Cheapflights users on 5/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:30 pm
ORD
- CYB
2 stops19h 55m
Multiple Airlines
Sat 11/287:10 am
CYB
- ORD
2 stops26h 50m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$976
This Delta deal was found by Cheapflights users on 5/28. 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 9/47:25 pm
ORD
- GCM
2 stops16h 14m
Delta
Tue 9/812:56 pm
GCM
- ORD
2 stops19h 00m
Delta
Deal found 5/28![Delta logo]()
$631
This Southwest deal was found by Cheapflights users on 5/26. 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 11/133:40 pm
MDW
- GCM
2 stops20h 20m
Southwest
Sat 11/214:10 pm
GCM
- MDW
1 stop7h 50m
Southwest
Deal found 5/26![Southwest logo]()
$632
This United Airlines deal was found by Cheapflights users on 5/27. 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.
Thu 7/28:02 pm
ORD
- GCM
1 stop16h 28m
United Airlines
Wed 7/81:35 pm
GCM
- ORD
1 stop8h 05m
United Airlines
Deal found 5/27![United Airlines logo]()
$681
This Southwest deal was found by Cheapflights users on 5/27. 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 7/25:10 am
MDW
- GCM
1 stop6h 45m
Southwest
Wed 7/812:50 pm
GCM
- MDW
2 stops10h 25m
Southwest
Deal found 5/27![Southwest logo]()
$634
This Delta deal was found by Cheapflights users on 5/28. 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.
Thu 9/36:42 pm
MDW
- GCM
2 stops16h 57m
Delta
Tue 9/812:56 pm
GCM
- MDW
2 stops19h 46m
Delta
Deal found 5/28![Delta logo]()
$641
This Delta deal was found by Cheapflights users on 5/27. 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.
Mon 9/145:30 am
ORD
- GCM
1 stop6h 10m
Delta
Sun 9/2012:55 pm
GCM
- ORD
1 stop8h 00m
Delta
Deal found 5/27![Delta logo]()
$646
This United Airlines deal was found by Cheapflights users on 5/27. 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 7/189:29 am
ORD
- GCM
Nonstop4h 01m
United Airlines
Sat 7/251:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 5/27![United Airlines logo]()
$717
This Southwest deal was found by Cheapflights users on 5/25. 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.
Fri 6/266:35 pm
MDW
- GCM
2 stops15h 55m
Southwest
Tue 6/3012:50 pm
GCM
- MDW
2 stops10h 20m
Southwest
Deal found 5/25![Southwest logo]()
$661
This Delta deal was found by Cheapflights users on 5/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:28 am
ORD
- GCM
1 stop6h 11m
Delta
Sun 8/301:04 pm
GCM
- ORD
1 stop7h 46m
Delta
Deal found 5/29![Delta logo]()
$661
This Southwest deal was found by Cheapflights users on 5/26. 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 9/55:00 am
MDW
- GCM
1 stop7h 05m
Southwest
Sat 9/121:00 pm
GCM
- MDW
2 stops16h 40m
Southwest
Deal found 5/26![Southwest logo]()
$679
This Delta deal was found by Cheapflights users on 5/27. 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.
Thu 9/105:30 am
ORD
- GCM
1 stop6h 10m
Delta
Sun 9/2012:55 pm
GCM
- ORD
1 stop8h 00m
Delta
Deal found 5/27![Delta logo]()
$681
This Southwest deal was found by Cheapflights users on 5/26. 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.
Wed 6/246:55 pm
MDW
- GCM
2 stops17h 00m
Southwest
Sat 6/271:05 pm
GCM
- MDW
1 stop9h 20m
Southwest
Deal found 5/26![Southwest logo]()
$731
This Delta deal was found by Cheapflights users on 5/27. 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.
Mon 9/145:30 am
ORD
- GCM
1 stop6h 10m
Delta
Fri 9/1812:55 pm
GCM
- ORD
1 stop11h 04m
Delta
Deal found 5/27![Delta logo]()
$686
This Delta deal was found by Cheapflights users on 5/26. 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 11/186:00 am
MDW
- GCM
1 stop5h 25m
Delta
Wed 11/251:50 pm
GCM
- MDW
1 stop8h 55m
Delta
Deal found 5/26![Delta logo]()
$686
This Delta deal was found by Cheapflights users on 5/27. 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 6/265:30 am
ORD
- GCM
1 stop6h 04m
Delta
Fri 7/1012:56 pm
GCM
- ORD
1 stop10h 57m
Delta
Deal found 5/27![Delta logo]()
$706
This Delta deal was found by Cheapflights users on 5/25. 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.
Fri 6/266:00 am
MDW
- GCM
1 stop5h 34m
Delta
Tue 6/3012:59 pm
GCM
- MDW
2 stops20h 15m
Delta
Deal found 5/25![Delta logo]()
$711
Last-minute flights from Chicago to Cayman IslandsDiscover last-minute flight deals from Chicago to Cayman Islands. Data last updated May 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Cayman Islands. Data last updated May 30, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 5/28. 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.
Sun 5/319:55 am
ORD
- GCM
1 stop25h 30m
Air Canada
Sat 6/610:55 am
GCM
- ORD
1 stop8h 30m
Air Canada
Deal found 5/28![Air Canada logo]()
$564
This FlightHub deal was found by Cheapflights users on 5/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/32:15 pm
ORD
- GCM
1 stop21h 10m
Air Canada
Sat 6/610:55 am
GCM
- ORD
1 stop7h 56m
Air Canada
Deal found 5/28![Air Canada logo]()
$385
This Southwest deal was found by Cheapflights users on 5/29. 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.
Sat 6/68:10 pm
MDW
- GCM
2 stops15h 45m
Southwest
Wed 6/1012:50 pm
GCM
- MDW
1 stop9h 10m
Southwest
Deal found 5/29![Southwest logo]()
$541
This Expedia deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/61:55 pm
ORD
- GCM
2 stops45h 30m
Multiple Airlines
Wed 6/107:00 am
GCM
- ORD
2 stops26h 00m
Multiple Airlines
Deal found 5/29![Multiple Airlines logo]()
$549
This Expedia deal was found by Cheapflights users on 5/26. 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 6/79:55 am
ORD
- GCM
1 stop25h 30m
Air Canada
Thu 6/1112:25 pm
GCM
- ORD
1 stop26h 30m
Air Canada
Deal found 5/26![Air Canada logo]()
$361
This Air Canada deal was found by Cheapflights users on 5/25. 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.
Sun 6/79:55 am
ORD
- GCM
1 stop25h 30m
Air Canada
Sat 6/1310:55 am
GCM
- ORD
1 stop22h 05m
Air Canada
Deal found 5/25![Air Canada logo]()
$387
This Justfly.com deal was found by Cheapflights users on 5/25. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/88:20 pm
ORD
- GCM
2 stops38h 05m
Multiple Airlines
Sat 6/1310:55 am
GCM
- ORD
1 stop22h 05m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$543
This Air Canada deal was found by Cheapflights users on 5/29. 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 6/122:00 pm
ORD
- GCM
1 stop20h 00m
Air Canada
Mon 6/2212:25 pm
GCM
- ORD
1 stop24h 57m
Air Canada
Deal found 5/29![Air Canada logo]()
$411
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/165:10 am
MDW
- GCM
1 stop6h 45m
Southwest
Sat 6/201:05 pm
GCM
- MDW
1 stop9h 20m
Southwest
Deal found 5/29![Southwest logo]()
$514
This Mytrip deal was found by Cheapflights users on 5/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/198:40 pm
ORD
- GCM
1 stop13h 20m
Multiple Airlines
Tue 6/231:45 pm
GCM
- ORD
1 stop8h 20m
Multiple Airlines
Deal found 5/29![Multiple Airlines logo]()
$546
This Kiwi.com deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1910:25 am
MDW
- GCM
1 stop26h 20m
Multiple Airlines
Tue 6/231:45 pm
GCM
- MDW
1 stop19h 55m
Multiple Airlines
Deal found 5/29![Multiple Airlines logo]()
$571
This Southwest deal was found by Cheapflights users on 5/29. 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.
Fri 6/196:35 pm
MDW
- GCM
2 stops15h 55m
Southwest
Tue 6/2312:50 pm
GCM
- MDW
2 stops10h 20m
Southwest
Deal found 5/29![Southwest logo]()
$572
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 May 30, 2026.
Search for one-way flight options from Chicago to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated May 30, 2026.
This Air Canada deal was found by Cheapflights users on 5/28. 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.
Wed 6/248:40 pm
ORD
- GCM
1 stop14h 45m
Air Canada
Deal found 5/28![Air Canada logo]()
$131
This Travelocity deal was found by Cheapflights users on 5/27. 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 6/238:35 am
ORD
- GCM
2 stops50h 50m
Air Canada
Deal found 5/27![Air Canada logo]()
$134
This Air Canada deal was found by Cheapflights users on 5/28. 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.
Wed 8/263:45 pm
ORD
- GCM
1 stop19h 40m
Air Canada
Deal found 5/28![Air Canada logo]()
$158
This Air Canada deal was found by Cheapflights users on 5/29. 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.
Tue 8/256:21 pm
ORD
- GCM
2 stops41h 04m
Air Canada
Deal found 5/29![Air Canada logo]()
$159
This Air Canada deal was found by Cheapflights users on 5/28. 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.
Fri 7/245:35 pm
ORD
- GCM
1 stop16h 25m
Air Canada
Deal found 5/28![Air Canada logo]()
$175
This Orbitz deal was found by Cheapflights users on 5/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/263:45 pm
ORD
- GCM
1 stop18h 00m
Air Canada
Deal found 5/30![Air Canada logo]()
$176
This Air Canada deal was found by Cheapflights users on 5/30. 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.
Wed 11/186:30 pm
ORD
- GCM
1 stop16h 30m
Air Canada
Deal found 5/30![Air Canada logo]()
$182
This Southwest deal was found by Cheapflights users on 5/25. 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.
Mon 8/35:10 am
MDW
- GCM
1 stop6h 45m
Southwest
Deal found 5/25![Southwest logo]()
$185
This Air Canada deal was found by Cheapflights users on 5/28. 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.
Sun 6/218:40 pm
ORD
- GCM
1 stop14h 45m
Air Canada
Deal found 5/28![Air Canada logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 5/28. 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 6/193:20 pm
MDW
- GCM
1 stop21h 25m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$245
This Southwest deal was found by Cheapflights users on 5/28. 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.
Mon 6/228:50 pm
MDW
- GCM
2 stops15h 05m
Southwest
Deal found 5/28![Southwest logo]()
$252
This Southwest deal was found by Cheapflights users on 5/28. 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.
Wed 11/185:15 am
MDW
- GCM
1 stop6h 20m
Southwest
Deal found 5/28![Southwest logo]()
$261
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 May 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $387 (Expedia) |
One-way from | $131 (Air Canada) |
Popular in | December |
Cheapest in | February |
Average price | $700 |
Good round-trip deal | $734 or less |
Good one-way deal | $384 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 May 30, 2026.
Use the filters below to find and compare flights from Chicago to the Cayman Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Tue 6/16
7:35 pm-11:55 am
2 stops16h 20m
George Town Owen Roberts Intl
Sat 6/20
1:05 pm-10:25 pm
1 stop9h 20m
$519
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 9/9
5:30 am-11:41 am
1 stop6h 11m
George Town Owen Roberts Intl
Fri 9/18
12:55 pm-8:02 am
2 stops19h 07m
$616
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Fri 9/4
7:25 pm-11:39 am
2 stops16h 14m
George Town Owen Roberts Intl
Tue 9/8
12:56 pm-7:56 am
2 stops19h 00m
$631
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Fri 11/13
3:40 pm-1:00 pm
2 stops20h 20m
George Town Owen Roberts Intl
Sat 11/21
4:10 pm-11:00 pm
1 stop7h 50m
$632
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Thu 7/2
5:10 am-11:55 am
1 stop6h 45m
George Town Owen Roberts Intl
Wed 7/8
12:50 pm-11:15 pm
2 stops10h 25m
$634
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Thu 9/3
6:42 pm-11:39 am
2 stops16h 57m
George Town Owen Roberts Intl
Tue 9/8
12:56 pm-8:42 am
2 stops19h 46m
$641
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Mon 9/14
5:30 am-11:40 am
1 stop6h 10m
George Town Owen Roberts Intl
Sun 9/20
12:55 pm-8:55 pm
1 stop8h 00m
$646
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 9/5
6:50 pm-11:30 am
1 stop16h 40m
George Town Owen Roberts Intl
Sat 9/12
11:55 am-11:50 pm
2 stops11h 55m
$651
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Fri 6/26
6:35 pm-10:30 am
2 stops15h 55m
George Town Owen Roberts Intl
Tue 6/30
12:50 pm-11:10 pm
2 stops10h 20m
$661
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 8/26
5:28 am-11:39 am
1 stop6h 11m
George Town Owen Roberts Intl
Sun 8/30
1:04 pm-8:50 pm
1 stop7h 46m
$661
Showing 1-10 of 35 resultsSorted by cheapest first
Best time to book a flight from Chicago to Cayman Islands
Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Chicago with our price prediction graph.
ORD-GCM
MDW-GCM
ORD-CYB
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to the Cayman Islands
CHI-KY0
ORD-GCM
MDW-GCM
ORD-CYB
What is the cheapest month to book a flight from Chicago to Cayman Islands?
Currently, December is the cheapest month in which you can book a flight from Chicago to Cayman Islands (average of $172). Flying from Chicago to Cayman Islands in September is currently the most expensive (average of $569). 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 May 30, 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 May 30, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Chicago to the Cayman Islands. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
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
See prices for flight routes from nearby airports that may be better suited for you.
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 May 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Cayman Islands regions
Consider these flights traveling to Cayman Islands regions.
Top 2 airlines flying from Chicago to Cayman Islands
Discover the top 2 airlines that operate flights from Chicago to Cayman Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$608 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$429 | Average$672 | FlexibilityNo cancel fee | On-time71% |