$133+ Cheap flights from Chicago (CHI) to Grand Cayman
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 6/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
5月 14 — 5月 211
Round-trip
1 adult, Economy
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Cheapest flights from Chicago to Grand CaymanExplore the most affordable flight options available from Chicago to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 4月 14, 2026.
Explore the most affordable flight options available from Chicago to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 4月 14, 2026.
This Air Canada deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週五 6/58:20 pm
ORD
- GCM
1 stop13h 40m
Air Canada
週一 6/812:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 4/14![Air Canada logo]()
$365
This Travelocity deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 6/66:22 pm
ORD
- GCM
2 stops41h 03m
Air Canada
週六 6/1310:55 am
GCM
- ORD
1 stop22h 05m
Air Canada
Deal found 4/14![Air Canada logo]()
$375
This Travelocity deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週四 6/46:22 pm
ORD
- GCM
2 stops39h 38m
Air Canada
週四 6/1112:25 pm
GCM
- ORD
2 stops19h 25m
Air Canada
Deal found 4/13![Air Canada logo]()
$378
This Expedia deal was found by Cheapflights users on 4/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週三 7/18:40 pm
ORD
- GCM
1 stop14h 45m
Air Canada
週一 7/612:25 pm
GCM
- ORD
1 stop7h 27m
Air Canada
Deal found 4/9![Air Canada logo]()
$395
This Travelocity deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 8/153:40 pm
ORD
- GCM
2 stops43h 45m
Air Canada
週四 8/2012:25 pm
GCM
- ORD
1 stop24h 57m
Air Canada
Deal found 4/13![Air Canada logo]()
$398
This Air Canada deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週五 8/149:50 am
ORD
- GCM
1 stop23h 55m
Air Canada
週六 8/2210:40 am
GCM
- ORD
1 stop22h 20m
Air Canada
Deal found 4/14![Air Canada logo]()
$405
This Flysmarter deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週日 10/45:57 pm
ORD
- GCM
1 stop17h 33m
Air Canada
週六 10/1012:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 4/14![Air Canada logo]()
$414
This Mytrip deal was found by Cheapflights users on 4/10. 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.
週一 5/259:20 am
ORD
- GCM
1 stop11h 55m
Multiple Airlines
週一 6/112:25 pm
GCM
- ORD
1 stop20h 35m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$415
This Mytrip deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週一 6/89:20 am
ORD
- GCM
1 stop11h 55m
Multiple Airlines
週六 6/1310:55 am
GCM
- ORD
1 stop22h 05m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週二 5/56:00 am
MDW
- GCM
1 stop6h 10m
Southwest
週五 5/81:05 pm
GCM
- MDW
1 stop11h 10m
Southwest
Deal found 4/14![Southwest logo]()
$492
This Southwest deal was found by Cheapflights users on 4/10. 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.
週一 5/45:35 am
MDW
- GCM
1 stop6h 35m
Southwest
週四 5/281:05 pm
GCM
- MDW
1 stop11h 10m
Southwest
Deal found 4/10![Southwest logo]()
$520
This Trip.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週四 6/46:00 am
MDW
- GCM
2 stops15h 15m
Multiple Airlines
週四 6/117:00 am
GCM
- MDW
2 stops15h 11m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$523
Best flights from Chicago to Grand CaymanDiscover carefully curated flight deals from Chicago to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 4月 14, 2026.
Discover carefully curated flight deals from Chicago to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 4月 14, 2026.
This Delta deal was found by Cheapflights users on 4/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週一 6/225:30 am
ORD
- GCM
1 stop6h 04m
Delta
週五 6/2612:59 pm
GCM
- ORD
1 stop9h 14m
Delta
Deal found 4/9![Delta logo]()
$553
This Southwest deal was found by Cheapflights users on 4/10. 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.
週一 5/45:30 am
MDW
- GCM
2 stops6h 40m
Southwest
週四 5/281:05 pm
GCM
- MDW
2 stops10h 50m
Southwest
Deal found 4/10![Southwest logo]()
$556
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 7/189:29 am
ORD
- GCM
Nonstop4h 01m
United Airlines
週三 7/221:35 pm
GCM
- ORD
1 stop11h 10m
United Airlines
Deal found 4/14![United Airlines logo]()
$584
This Delta deal was found by Cheapflights users on 4/10. 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.
週一 6/15:30 am
ORD
- GCM
1 stop6h 24m
Delta
週五 6/51:19 pm
GCM
- ORD
1 stop10h 40m
Delta
Deal found 4/10![Delta logo]()
$553
This Southwest deal was found by Cheapflights users on 4/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週二 5/268:50 pm
MDW
- GCM
2 stops15h 20m
Southwest
週二 6/21:05 pm
GCM
- MDW
1 stop8h 20m
Southwest
Deal found 4/11![Southwest logo]()
$598
This Delta deal was found by Cheapflights users on 4/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週一 6/87:17 pm
ORD
- GCM
2 stops16h 17m
Delta
週五 6/2612:59 pm
GCM
- ORD
2 stops21h 36m
Delta
Deal found 4/9![Delta logo]()
$558
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週三 5/276:50 pm
MDW
- GCM
2 stops17h 20m
Southwest
週三 6/31:05 pm
GCM
- MDW
1 stop8h 20m
Southwest
Deal found 4/12![Southwest logo]()
$608
This Delta deal was found by Cheapflights users on 4/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週日 6/77:17 pm
ORD
- GCM
2 stops16h 17m
Delta
週五 6/2612:59 pm
GCM
- ORD
1 stop9h 14m
Delta
Deal found 4/9![Delta logo]()
$558
This Delta deal was found by Cheapflights users on 4/10. 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.
週二 6/235:30 am
ORD
- GCM
1 stop6h 04m
Delta
週日 6/2812:59 pm
GCM
- ORD
1 stop11h 00m
Delta
Deal found 4/10![Delta logo]()
$588
This Delta deal was found by Cheapflights users on 4/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週四 6/117:59 pm
ORD
- GCM
1 stop15h 35m
Delta
週三 6/2412:59 pm
GCM
- ORD
1 stop7h 33m
Delta
Deal found 4/9![Delta logo]()
$588
This Delta deal was found by Cheapflights users on 4/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週一 6/85:30 am
ORD
- GCM
1 stop6h 04m
Delta
週一 6/2212:59 pm
GCM
- ORD
1 stop7h 33m
Delta
Deal found 4/9![Delta logo]()
$588
This Delta deal was found by Cheapflights users on 4/10. 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.
週二 6/236:05 am
MDW
- GCM
1 stop5h 29m
Delta
週日 6/2812:59 pm
GCM
- MDW
1 stop9h 18m
Delta
Deal found 4/10![Delta logo]()
$588
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週日 8/165:30 am
ORD
- GCM
1 stop6h 11m
Delta
週二 8/2512:56 pm
GCM
- ORD
1 stop7h 21m
Delta
Deal found 4/14![Delta logo]()
$602
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週三 8/195:30 am
ORD
- GCM
1 stop6h 11m
Delta
週二 8/2512:56 pm
GCM
- ORD
1 stop11h 01m
Delta
Deal found 4/14![Delta logo]()
$602
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週一 8/176:00 am
MDW
- GCM
1 stop5h 41m
Delta
週三 8/2612:56 pm
GCM
- MDW
2 stops19h 46m
Delta
Deal found 4/14![Delta logo]()
$602
This Delta deal was found by Cheapflights users on 4/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週二 8/185:30 am
ORD
- GCM
1 stop6h 11m
Delta
週二 8/2512:56 pm
GCM
- ORD
1 stop11h 01m
Delta
Deal found 4/9![Delta logo]()
$611
This Delta deal was found by Cheapflights users on 4/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週一 8/245:30 am
ORD
- GCM
1 stop6h 11m
Delta
週二 8/2512:56 pm
GCM
- ORD
1 stop11h 01m
Delta
Deal found 4/9![Delta logo]()
$611
This Delta deal was found by Cheapflights users on 4/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週二 8/186:00 am
MDW
- GCM
1 stop5h 41m
Delta
週二 8/2512:56 pm
GCM
- MDW
1 stop8h 50m
Delta
Deal found 4/9![Delta logo]()
$611
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週三 8/126:00 am
MDW
- GCM
1 stop5h 41m
Delta
週三 8/1912:56 pm
GCM
- MDW
1 stop8h 50m
Delta
Deal found 4/13![Delta logo]()
$611
This Delta deal was found by Cheapflights users on 4/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週日 8/235:59 pm
MDW
- GCM
2 stops17h 42m
Delta
週二 8/2512:56 pm
GCM
- MDW
2 stops19h 46m
Delta
Deal found 4/9![Delta logo]()
$616
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 6/66:23 am
MDW
- GCM
1 stop5h 31m
Delta
週日 6/1412:59 pm
GCM
- MDW
1 stop9h 18m
Delta
Deal found 4/13![Delta logo]()
$623
This Delta deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週二 5/266:23 am
MDW
- GCM
1 stop5h 31m
Delta
週六 5/301:19 pm
GCM
- MDW
1 stop7h 50m
Delta
Deal found 4/12![Delta logo]()
$640
This Delta deal was found by Cheapflights users on 4/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 8/226:00 am
MDW
- GCM
1 stop5h 41m
Delta
週三 8/2612:56 pm
GCM
- MDW
1 stop8h 50m
Delta
Deal found 4/11![Delta logo]()
$646
Last-minute flights from Chicago to Grand CaymanDiscover last-minute flight deals from Chicago to Grand Cayman. Data last updated 4月 14, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Grand Cayman. Data last updated 4月 14, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週日 4/197:55 am
ORD
- GCM
1 stop26h 20m
Air Canada
週五 4/2411:10 am
GCM
- ORD
1 stop22h 00m
Air Canada
Deal found 4/14![Air Canada logo]()
$445
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週一 4/204:58 pm
ORD
- GCM
1 stop23h 07m
Multiple Airlines
週三 5/611:30 am
GCM
- ORD
1 stop29h 20m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$429
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週一 4/204:58 pm
ORD
- GCM
1 stop23h 07m
Multiple Airlines
週二 5/511:30 am
GCM
- ORD
2 stops20h 25m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$468
This Kiwi.com deal was found by Cheapflights users on 4/10. 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.
週五 5/17:50 am
ORD
- GCM
1 stop13h 45m
Multiple Airlines
週三 5/611:30 am
GCM
- ORD
1 stop29h 20m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$436
This Southwest deal was found by Cheapflights users on 4/10. 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.
週一 5/45:35 am
MDW
- GCM
1 stop6h 35m
Southwest
週四 5/281:05 pm
GCM
- MDW
1 stop11h 10m
Southwest
Deal found 4/10![Southwest logo]()
$520
This Southwest deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週二 5/56:00 am
MDW
- GCM
1 stop6h 10m
Southwest
週五 5/81:05 pm
GCM
- MDW
1 stop11h 10m
Southwest
Deal found 4/14![Southwest logo]()
$492
This Southwest deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週二 5/56:00 am
MDW
- GCM
1 stop6h 10m
Southwest
週四 5/71:05 pm
GCM
- MDW
1 stop11h 10m
Southwest
Deal found 4/14![Southwest logo]()
$584
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週三 5/61:59 pm
ORD
- GCM
2 stops21h 36m
Multiple Airlines
週日 5/105:05 pm
GCM
- ORD
1 stop6h 51m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$464
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週三 5/131:59 pm
ORD
- GCM
2 stops21h 36m
Multiple Airlines
週一 5/187:00 am
GCM
- ORD
1 stop16h 56m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$466
This Mytrip deal was found by Cheapflights users on 4/10. 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.
週一 5/259:20 am
ORD
- GCM
1 stop11h 55m
Multiple Airlines
週一 6/112:25 pm
GCM
- ORD
1 stop20h 35m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$415
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週二 5/2612:27 pm
MDW
- GCM
2 stops27h 38m
Multiple Airlines
週六 5/301:45 pm
GCM
- MDW
1 stop20h 00m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$588
This Expedia deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 5/3010:41 am
ORD
- GCM
2 stops48h 44m
Air Canada
週六 6/610:55 am
GCM
- ORD
2 stops20h 50m
Air Canada
Deal found 4/14![Air Canada logo]()
$433
One-way flights from Chicago to Grand CaymanSearch for one-way flight options from Chicago to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated 4月 14, 2026.
Search for one-way flight options from Chicago to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated 4月 14, 2026.
This Expedia deal was found by Cheapflights users on 4/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週三 6/108:20 pm
ORD
- GCM
1 stop15h 05m
Air Canada
Deal found 4/10![Air Canada logo]()
$133
This Air Canada deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週五 6/1210:41 am
ORD
- GCM
2 stops23h 19m
Air Canada
Deal found 4/14![Air Canada logo]()
$138
This Travelocity deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週五 8/219:50 am
ORD
- GCM
1 stop23h 55m
Air Canada
Deal found 4/10![Air Canada logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 4/10. 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.
週四 5/75:45 pm
ORD
- GCM
1 stop27h 50m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$149
This Orbitz deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 7/113:40 pm
ORD
- GCM
2 stops43h 45m
Air Canada
Deal found 4/12![Air Canada logo]()
$151
This Air Canada deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週日 7/125:35 pm
ORD
- GCM
1 stop17h 50m
Air Canada
Deal found 4/14![Air Canada logo]()
$153
This Air Canada deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週五 7/107:10 am
ORD
- GCM
2 stops26h 45m
Air Canada
Deal found 4/14![Air Canada logo]()
$156
This Air Canada deal was found by Cheapflights users on 4/10. 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.
週三 10/72:00 pm
ORD
- GCM
2 stops21h 30m
Air Canada
Deal found 4/10![Air Canada logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 4/10. 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.
週一 5/119:20 am
ORD
- GCM
1 stop11h 55m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$173
This Southwest deal was found by Cheapflights users on 4/10. 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.
週日 5/105:05 am
MDW
- GCM
1 stop6h 50m
Southwest
Deal found 4/10![Southwest logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 4/10. 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.
週六 7/117:10 am
ORD
- GCM
1 stop28h 25m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 4/10. 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.
週二 5/126:00 am
MDW
- GCM
2 stops10h 05m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$187
Find flight deals from Chicago to Grand Cayman
Keep the following information in mind while searching for Chicago to Grand Cayman flight deals. Data was last updated 4月 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $365 (Air Canada) |
One-way from | $133 (Expedia) |
Popular in | December |
Cheapest in | February |
Average price | $630 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Grand Cayman 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 4月 14, 2026.
Use the filters below to find and compare flights from Chicago to Grand Cayman that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
週一 6/22
5:30 am-11:34 am
1 stop6h 04m
George Town Owen Roberts Intl
週五 6/26
12:59 pm-10:13 pm
1 stop9h 14m
$553
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
週一 6/1
5:30 am-11:54 am
1 stop6h 24m
George Town Owen Roberts Intl
週五 6/5
1:19 pm-11:59 pm
1 stop10h 40m
$553
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
週一 5/4
5:30 am-12:10 pm
2 stops6h 40m
George Town Owen Roberts Intl
週四 5/28
1:05 pm-11:55 pm
2 stops10h 50m
$556
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
週一 6/8
7:17 pm-11:34 am
2 stops16h 17m
George Town Owen Roberts Intl
週五 6/26
12:59 pm-10:35 am
2 stops21h 36m
$558
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
週日 6/7
7:17 pm-11:34 am
2 stops16h 17m
George Town Owen Roberts Intl
週五 6/26
12:59 pm-10:13 pm
1 stop9h 14m
$558
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
週六 7/18
9:29 am-1:30 pm
Nonstop4h 01m
George Town Owen Roberts Intl
週三 7/22
1:35 pm-12:45 am
1 stop11h 10m
$584
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
週二 6/23
5:30 am-11:34 am
1 stop6h 04m
George Town Owen Roberts Intl
週日 6/28
12:59 pm-11:59 pm
1 stop11h 00m
$588
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
週四 6/11
7:59 pm-11:34 am
1 stop15h 35m
George Town Owen Roberts Intl
週三 6/24
12:59 pm-8:32 pm
1 stop7h 33m
$588
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
週一 6/8
5:30 am-11:34 am
1 stop6h 04m
George Town Owen Roberts Intl
週一 6/22
12:59 pm-8:32 pm
1 stop7h 33m
$588
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
週二 6/23
6:05 am-11:34 am
1 stop5h 29m
George Town Owen Roberts Intl
週日 6/28
12:59 pm-10:17 pm
1 stop9h 18m
$588
Showing 1-10 of 46 resultsSorted by cheapest first
Best time to book a flight from Chicago to Grand Cayman
Have a flexible travel schedule? Discover the best time to fly to Grand Cayman from Chicago with our price prediction graph.
ORD-GCM
MDW-GCM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Grand Cayman
CHI-zzLAW
ORD-GCM
MDW-GCM
What is the cheapest month to book a flight from Chicago to Grand Cayman?
Currently, December is the cheapest month in which you can book a flight from Chicago to Grand Cayman (average of $322). Flying from Chicago to Grand Cayman in September is currently the most expensive (average of $661). 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 LAW?
Find hourly flight availability from Chicago to Grand Cayman. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 4月 14, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Grand Cayman as you normally would.
Reviews of airlines servicing Grand Cayman
Get insights into the airlines that provide service to Grand Cayman. 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 Grand Cayman. Reviews last updated 4月 14, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Chicago to Grand Cayman. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Chicago to Grand Cayman. 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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Complete your trip
Complete your trip to Grand Cayman by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Grand Cayman by cabin class
Find flights from Chicago to Grand Cayman, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Grand Cayman flights
Browse other Chicago and Grand Cayman flight options. Last updated on 4月 14, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Chicago to Grand Cayman
Discover the top 2 airlines that operate flights from Chicago to Grand Cayman. 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 4月 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$603 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$429 | Average$673 | FlexibilityNo cancel fee | On-time71% |