$135+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Sep 24 — Oct 11
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Grand Cayman with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Chicago to 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 August 25, 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 August 25, 2026.
This Air Canada deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:40 pm -
1 stop14h 30m
Sat 10/3112:10 pm -
1 stop8h 03m
Deal found 8/20![Air Canada logo]()
$367
This Orbitz deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:40 pm -
1 stop14h 30m
Wed 10/2812:10 pm -
1 stop21h 13m
Deal found 8/24![Air Canada logo]()
$369
This Air Canada deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/243:40 pm -
2 stops19h 30m
Fri 10/3012:10 pm -
2 stops19h 50m
Deal found 8/24![Air Canada logo]()
$391
This Air Canada deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/148:50 pm -
1 stop14h 20m
Sat 11/211:10 pm -
1 stop7h 48m
Deal found 8/20![Air Canada logo]()
$393
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/135:10 am -
1 stop6h 25m
Wed 12/161:30 pm -
1 stop7h 00m
Deal found 8/23![Southwest logo]()
$454
This Southwest deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/24:10 pm -
2 stops19h 25m
Wed 12/91:30 pm -
1 stop8h 45m
Deal found 8/22![Southwest logo]()
$489
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2511:45 am -
1 stop25h 00m
Thu 10/17:00 am -
2 stops16h 44m
Deal found 8/23![Multiple Airlines logo]()
$559
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/95:20 am -
1 stop6h 15m
Sun 12/131:30 pm -
1 stop8h 05m
Deal found 8/24![Southwest logo]()
$563
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/315:20 am -
1 stop6h 15m
Wed 1/61:50 pm -
2 stops16h 50m
Deal found 8/24![Southwest logo]()
$603
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:00 am -
1 stop5h 43m
Sat 11/212:08 pm -
1 stop9h 46m
Deal found 8/24![Delta logo]()
$681
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:25 am -
1 stop6h 10m
Mon 11/301:30 pm -
2 stops8h 35m
Deal found 8/23![Southwest logo]()
$692
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:20 pm -
1 stop21h 25m
Mon 10/1212:40 pm -
2 stops11h 03m
Deal found 8/21![Multiple Airlines logo]()
$698
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 August 25, 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 August 25, 2026.
This Orbitz deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/281:55 pm -
2 stops45h 15m
Sun 11/11:10 pm -
1 stop29h 33m
Deal found 8/20![Air Canada logo]()
$396
This Mytrip deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/245:35 pm -
1 stop17h 35m
Wed 10/287:00 am -
3 stops28h 07m
Deal found 8/20![Multiple Airlines logo]()
$571
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:52 pm -
1 stop16h 23m
Sat 10/311:55 pm -
Nonstop4h 18m
Deal found 8/20![United Airlines logo]()
$671
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:49 pm -
1 stop15h 34m
Sat 11/214:25 pm -
Nonstop4h 40m
Deal found 8/24![American Airlines logo]()
$671
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/226:04 am -
1 stop5h 36m
Sun 10/2512:55 pm -
1 stop9h 38m
Deal found 8/20![Delta logo]()
$681
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:00 am -
1 stop7h 05m
Sat 9/121:00 pm -
2 stops16h 40m
Deal found 8/24![Southwest logo]()
$722
This Air Canada deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/115:54 pm -
2 stops41h 16m
Sun 11/151:10 pm -
1 stop7h 48m
Deal found 8/21![Air Canada logo]()
$475
This Travelocity deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/208:50 pm -
1 stop14h 20m
Tue 11/241:10 pm -
1 stop7h 48m
Deal found 8/24![Air Canada logo]()
$492
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:00 am -
1 stop5h 43m
Sat 11/212:08 pm -
1 stop9h 46m
Deal found 8/24![Delta logo]()
$681
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:55 pm -
1 stop16h 35m
Sat 10/101:35 pm -
1 stop8h 07m
Deal found 8/24![United Airlines logo]()
$681
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:00 am -
1 stop6h 30m
Thu 10/152:10 pm -
1 stop10h 28m
Deal found 8/24![American Airlines logo]()
$681
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/195:27 am -
1 stop6h 13m
Fri 10/2312:55 pm -
1 stop7h 43m
Deal found 8/20![Delta logo]()
$681
This Booking.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/142:15 pm -
1 stop21h 10m
Sat 10/1711:25 am -
1 stop8h 23m
Deal found 8/22![Air Canada logo]()
$629
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/35:00 am -
1 stop7h 10m
Sat 10/101:05 pm -
1 stop6h 15m
Deal found 8/24![Southwest logo]()
$773
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/208:40 pm -
2 stops17h 30m
Tue 11/241:30 pm -
1 stop6h 35m
Deal found 8/24![Southwest logo]()
$848
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:05 am -
1 stop5h 35m
Sun 9/131:00 pm -
1 stop9h 44m
Deal found 8/22![Delta logo]()
$856
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:05 am -
1 stop5h 35m
Mon 10/1212:55 pm -
1 stop9h 38m
Deal found 8/21![Delta logo]()
$906
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:04 am -
1 stop5h 36m
Thu 10/2212:55 pm -
1 stop9h 38m
Deal found 8/23![Delta logo]()
$906
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:05 am -
1 stop5h 34m
Sun 9/61:04 pm -
1 stop9h 32m
Deal found 8/21![Delta logo]()
$946
Last-minute flights from Chicago to Grand CaymanDiscover last-minute flight deals from Chicago to Grand Cayman. Data last updated August 25, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Grand Cayman. Data last updated August 25, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:05 am -
2 stops15h 10m
Sun 9/67:00 am -
2 stops15h 47m
Deal found 8/21![Multiple Airlines logo]()
$816
This Justfly.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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.
Sat 9/56:21 pm -
2 stops41h 04m
Sat 9/1210:40 am -
1 stop8h 11m
Deal found 8/20![Air Canada logo]()
$418
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:00 am -
1 stop7h 05m
Sat 9/121:00 pm -
1 stop8h 00m
Deal found 8/24![Southwest logo]()
$717
This Air Canada deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:55 am -
1 stop23h 50m
Sat 9/1910:40 am -
1 stop26h 43m
Deal found 8/23![Air Canada logo]()
$443
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:05 am -
1 stop5h 35m
Sun 9/131:00 pm -
1 stop9h 44m
Deal found 8/22![Delta logo]()
$856
This Mytrip deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/138:40 pm -
1 stop14h 45m
Fri 9/187:00 am -
2 stops25h 55m
Deal found 8/23![Multiple Airlines logo]()
$558
This Expedia deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:45 am -
2 stops50h 40m
Thu 9/2412:25 pm -
1 stop20h 35m
Deal found 8/24![Air Canada logo]()
$409
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:00 pm -
1 stop16h 00m
Mon 9/2812:00 pm -
1 stop11h 30m
Deal found 8/24![American Airlines logo]()
$681
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:05 am -
1 stop5h 35m
Mon 9/281:00 pm -
1 stop9h 44m
Deal found 8/24![Delta logo]()
$681
This Travelocity deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:45 pm -
1 stop18h 00m
Thu 10/112:25 pm -
1 stop20h 35m
Deal found 8/23![Air Canada logo]()
$433
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2511:45 am -
1 stop25h 00m
Thu 10/17:00 am -
2 stops16h 44m
Deal found 8/23![Multiple Airlines logo]()
$559
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:05 am -
1 stop5h 35m
Thu 10/11:00 pm -
1 stop9h 44m
Deal found 8/23![Delta logo]()
$721
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 August 25, 2026.
Search for one-way flight options from Chicago to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated August 25, 2026.
This Expedia deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:40 pm -
1 stop13h 50m
Deal found 8/24![Air Canada logo]()
$135
This Air Canada deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/187:11 am -
2 stops28h 14m
Deal found 8/20![Air Canada logo]()
$142
This Expedia deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:40 pm -
1 stop14h 45m
Deal found 8/23![Air Canada logo]()
$145
This Air Canada deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:40 pm -
1 stop13h 50m
Deal found 8/21![Air Canada logo]()
$150
This Air Canada deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/223:40 pm -
2 stops42h 50m
Deal found 8/21![Air Canada logo]()
$153
This Air Canada deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/314:30 pm -
1 stop19h 40m
Deal found 8/24![Air Canada logo]()
$155
This Travelocity deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/198:45 am -
2 stops50h 40m
Deal found 8/20![Air Canada logo]()
$158
This Air Canada deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/162:15 pm -
1 stop21h 10m
Deal found 8/20![Air Canada logo]()
$160
This Air Canada deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:40 pm -
2 stops18h 05m
Deal found 8/20![Air Canada logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:12 pm -
2 stops22h 23m
Deal found 8/23![Multiple Airlines logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:12 pm -
3 stops25h 38m
Deal found 8/24![Multiple Airlines logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/171:12 pm -
2 stops22h 23m
Deal found 8/24![Multiple Airlines logo]()
$261
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 August 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $367 (Air Canada) |
One-way from | $135 (Expedia) |
Popular in | July |
Cheapest in | February |
Average price | $691 |
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 7,457,451 searches. Data last updated August 25, 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 Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Wed 10/28
1:55 pm-11:10 am
2 stops45h 15m
George Town Owen Roberts Intl
Sun 11/1
1:10 pm-5:43 pm
1 stop29h 33m
$396
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Wed 11/11
5:54 pm-12:10 pm
2 stops41h 16m
George Town Owen Roberts Intl
Sun 11/15
1:10 pm-7:58 pm
1 stop7h 48m
$475
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Fri 11/20
8:50 pm-12:10 pm
1 stop14h 20m
George Town Owen Roberts Intl
Tue 11/24
1:10 pm-7:58 pm
1 stop7h 48m
$492
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Sat 10/24
5:35 pm-11:10 am
1 stop17h 35m
George Town Owen Roberts Intl
Wed 10/28
7:00 am-11:07 am
3 stops28h 07m
$571
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Wed 10/14
2:15 pm-11:25 am
1 stop21h 10m
George Town Owen Roberts Intl
Sat 10/17
11:25 am-7:48 pm
1 stop8h 23m
$629
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Sat 10/24
7:52 pm-12:15 pm
1 stop16h 23m
George Town Owen Roberts Intl
Sat 10/31
1:55 pm-6:13 pm
Nonstop4h 18m
$671
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Sat 11/14
6:49 pm-11:23 am
1 stop15h 34m
George Town Owen Roberts Intl
Sat 11/21
4:25 pm-8:05 pm
Nonstop4h 40m
$671
ChicagoGeorge Town
MDW Chicago Midway - GCM George Town Owen Roberts Intl
MDWGCM
Chicago Midway
Thu 10/22
6:04 am-11:40 am
1 stop5h 36m
George Town Owen Roberts Intl
Sun 10/25
12:55 pm-10:33 pm
1 stop9h 38m
$681
ChicagoGeorge Town
MDW Chicago Midway - GCM George Town Owen Roberts Intl
MDWGCM
Chicago Midway
Sat 11/14
6:00 am-12:43 pm
1 stop5h 43m
George Town Owen Roberts Intl
Sat 11/21
2:08 pm-10:54 pm
1 stop9h 46m
$681
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Sat 10/3
7:55 pm-12:30 pm
1 stop16h 35m
George Town Owen Roberts Intl
Sat 10/10
1:35 pm-9:42 pm
1 stop8h 07m
$681
Showing 1-10 of 33 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, February is the cheapest month in which you can book a flight from Chicago to Grand Cayman (average of $530). Flying from Chicago to Grand Cayman in November is currently the most expensive (average of $873). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How far ahead should I book a flight from Chicago to Grand Cayman?
Booking 1 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Grand Cayman. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
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 August 25, 2026.
Read reviews from past customers who have flown Delta,United Airlines, andAmerican 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.
Entertainment
7.8
Overall
7.8
Comfort
7.8
Boarding
8.1
Food
7.2
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Entertainment
7.8
Overall
7.8
Comfort
7.8
Boarding
8.1
Food
7.2
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Entertainment
7.8
Overall
7.8
Comfort
7.8
Boarding
8.1
Food
7.2
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Entertainment
7.8
Overall
7.8
Comfort
7.8
Boarding
8.1
Food
7.2
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Related info for your journey
Find useful and relevant information for your journey from Chicago to 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 August 25, 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 7,457,451 searches. Data last updated August 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$616 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$438 | Average$695 | FlexibilityNo cancel fee | On-time71% |