$134+ 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 6/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Jun 27 — Jul 41
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Grand Cayman with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 May 28, 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 May 28, 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 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 5/23. 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.
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 5/23![Air Canada logo]()
$407
This Orbitz deal was found by Cheapflights users on 5/24. 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 9/193:40 pm
ORD
- GCM
2 stops43h 50m
Air Canada
Sat 9/2612:25 pm
GCM
- ORD
1 stop26h 30m
Air Canada
Deal found 5/24![Air Canada logo]()
$410
This Air Canada deal was found by Cheapflights users on 5/24. 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.
Sun 10/113:40 pm
ORD
- GCM
2 stops19h 50m
Air Canada
Sat 10/1712:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 5/24![Air Canada logo]()
$413
This Expedia deal was found by Cheapflights users on 5/23. 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.
Fri 6/58:20 pm
ORD
- GCM
1 stop13h 40m
Air Canada
Mon 6/812:25 pm
GCM
- ORD
1 stop28h 34m
Air Canada
Deal found 5/23![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 FlightHub deal was found by Cheapflights users on 5/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/318:40 pm
ORD
- GCM
1 stop13h 05m
Air Canada
Sat 8/810:40 am
GCM
- ORD
1 stop22h 20m
Air Canada
Deal found 5/24![Air Canada logo]()
$421
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 11/135:10 am
MDW
- GCM
1 stop6h 25m
Southwest
Sat 11/214:10 pm
GCM
- MDW
1 stop7h 50m
Southwest
Deal found 5/26![Southwest logo]()
$612
This Southwest deal was found by Cheapflights users on 5/24. 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 9/195:00 am
MDW
- GCM
1 stop7h 05m
Southwest
Sat 9/261:00 pm
GCM
- MDW
1 stop7h 55m
Southwest
Deal found 5/24![Southwest logo]()
$627
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
1 stop7h 20m
Southwest
Deal found 5/27![Southwest logo]()
$629
This Southwest deal was found by Cheapflights users on 5/23. 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.
Fri 7/175:10 am
MDW
- GCM
1 stop6h 45m
Southwest
Fri 7/2412:50 pm
GCM
- MDW
1 stop8h 35m
Southwest
Deal found 5/23![Southwest logo]()
$633
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 May 28, 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 May 28, 2026.
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 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 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 5/24. 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.
Mon 8/35:30 am
ORD
- GCM
1 stop7h 00m
United Airlines
Fri 8/71:35 pm
GCM
- ORD
1 stop9h 40m
United Airlines
Deal found 5/24![United Airlines logo]()
$661
This Southwest deal was found by Cheapflights users on 5/23. 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.
Fri 7/175:10 am
MDW
- GCM
1 stop6h 45m
Southwest
Fri 7/2412:50 pm
GCM
- MDW
1 stop8h 35m
Southwest
Deal found 5/23![Southwest logo]()
$633
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 5/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:30 am
ORD
- GCM
1 stop6h 55m
United Airlines
Sat 10/311:50 pm
GCM
- ORD
Nonstop4h 14m
United Airlines
Deal found 5/25![United Airlines logo]()
$671
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:34 pm
ORD
- GCM
1 stop14h 26m
American Airlines
Sat 10/243:20 pm
GCM
- ORD
1 stop7h 52m
American Airlines
Deal found 5/27![American 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 5/24. 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 8/226:05 am
MDW
- GCM
1 stop5h 34m
Delta
Wed 8/261:04 pm
GCM
- MDW
1 stop9h 32m
Delta
Deal found 5/24![Delta logo]()
$646
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 Delta deal was found by Cheapflights users on 5/23. 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.
Wed 10/77:35 pm
ORD
- GCM
2 stops16h 05m
Delta
Mon 10/1212:55 pm
GCM
- ORD
1 stop7h 25m
Delta
Deal found 5/23![Delta logo]()
$651
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 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 Delta deal was found by Cheapflights users on 5/24. 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.
Wed 7/295:30 am
ORD
- GCM
1 stop6h 01m
Delta
Tue 8/41:04 pm
GCM
- ORD
2 stops21h 38m
Delta
Deal found 5/24![Delta logo]()
$666
This Southwest deal was found by Cheapflights users on 5/23. 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.
Fri 6/266:35 pm
MDW
- GCM
2 stops15h 55m
Southwest
Fri 7/312:50 pm
GCM
- MDW
1 stop8h 35m
Southwest
Deal found 5/23![Southwest logo]()
$690
This Delta deal was found by Cheapflights users on 5/24. 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.
Sun 8/26:58 pm
MDW
- GCM
2 stops16h 41m
Delta
Tue 8/41:04 pm
GCM
- MDW
1 stop9h 32m
Delta
Deal found 5/24![Delta logo]()
$666
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 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
Last-minute flights from Chicago to Grand CaymanDiscover last-minute flight deals from Chicago to Grand Cayman. Data last updated May 28, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Grand Cayman. Data last updated May 28, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/23. 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.
Thu 5/285:35 am
MDW
- GCM
1 stop6h 35m
Southwest
Sat 5/301:05 pm
GCM
- MDW
1 stop7h 20m
Southwest
Deal found 5/23![Southwest logo]()
$641
This Expedia deal was found by Cheapflights users on 5/23. 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.
Fri 6/58:20 pm
ORD
- GCM
1 stop13h 40m
Air Canada
Mon 6/812:25 pm
GCM
- ORD
1 stop28h 34m
Air Canada
Deal found 5/23![Air Canada logo]()
$415
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.
Fri 6/55:10 am
MDW
- GCM
1 stop6h 45m
Southwest
Tue 6/912:50 pm
GCM
- MDW
1 stop7h 25m
Southwest
Deal found 5/28![Southwest logo]()
$651
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
Mon 6/1512:25 pm
GCM
- ORD
1 stop25h 00m
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 Orbitz deal was found by Cheapflights users on 5/23. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/86:15 am
ORD
- GCM
2 stops30h 30m
Multiple Airlines
Mon 6/1512:25 pm
GCM
- ORD
1 stop28h 34m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$569
This Southwest deal was found by Cheapflights users on 5/23. 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.
Mon 6/88:50 pm
MDW
- GCM
2 stops15h 05m
Southwest
Mon 6/1512:50 pm
GCM
- MDW
2 stops9h 05m
Southwest
Deal found 5/23![Southwest logo]()
$673
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.
Wed 6/102:15 pm
ORD
- GCM
1 stop21h 10m
Air Canada
Mon 6/1512:25 pm
GCM
- ORD
1 stop25h 00m
Air Canada
Deal found 5/25![Air Canada logo]()
$600
This Mytrip 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 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 5/25![Multiple Airlines logo]()
$554
This FlightHub deal was found by Cheapflights users on 5/23. 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 FlightHub 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
Multiple Airlines
Sat 7/42:10 pm
GCM
- ORD
1 stop26h 06m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$584
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
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 May 28, 2026.
Search for one-way flight options from Chicago to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated May 28, 2026.
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 5/24. 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.
Wed 6/178:25 pm
ORD
- GCM
1 stop15h 00m
Air Canada
Deal found 5/24![Air Canada logo]()
$138
This Travelocity deal was found by Cheapflights users on 5/24. 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.
Sat 6/206:04 pm
ORD
- GCM
2 stops41h 21m
Air Canada
Deal found 5/24![Air Canada logo]()
$141
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/243:45 pm
ORD
- GCM
1 stop19h 40m
Air Canada
Deal found 5/27![Air Canada logo]()
$144
This Travelocity deal was found by Cheapflights users on 5/23. 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.
Sun 7/123:45 pm
ORD
- GCM
1 stop19h 40m
Air Canada
Deal found 5/23![Air Canada logo]()
$157
This Air Canada 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 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 5/27![Air Canada logo]()
$158
This Air Canada deal was found by Cheapflights users on 5/23. 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.
Sun 8/166:21 pm
ORD
- GCM
2 stops17h 04m
Air Canada
Deal found 5/23![Air Canada logo]()
$162
This Air Canada deal was found by Cheapflights users on 5/24. 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.
Fri 8/218:45 am
ORD
- GCM
2 stops25h 00m
Air Canada
Deal found 5/24![Air Canada logo]()
$165
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 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 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:30 pm
ORD
- GCM
1 stop16h 30m
Air Canada
Deal found 5/27![Air Canada logo]()
$191
This Air Canada 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 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 5/27![Air Canada logo]()
$193
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 May 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $361 (Expedia) |
One-way from | $134 (Travelocity) |
Popular in | December |
Cheapest in | February |
Average price | $700 |
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 May 28, 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
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
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
Fri 7/17
5:10 am-11:55 am
1 stop6h 45m
George Town Owen Roberts Intl
Fri 7/24
12:50 pm-9:25 pm
1 stop8h 35m
$633
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
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
MDW - GCM
MDWGCM
Chicago Midway
Sat 8/22
6:05 am-11:39 am
1 stop5h 34m
George Town Owen Roberts Intl
Wed 8/26
1:04 pm-10:36 pm
1 stop9h 32m
$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
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 10/7
7:35 pm-11:40 am
2 stops16h 05m
George Town Owen Roberts Intl
Mon 10/12
12:55 pm-8:20 pm
1 stop7h 25m
$651
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Mon 8/3
5:30 am-12:30 pm
1 stop7h 00m
George Town Owen Roberts Intl
Fri 8/7
1:35 pm-11:15 pm
1 stop9h 40m
$661
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 7/29
5:30 am-11:31 am
1 stop6h 01m
George Town Owen Roberts Intl
Tue 8/4
1:04 pm-10:42 am
2 stops21h 38m
$666
Showing 1-10 of 36 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 $172). Flying from Chicago to Grand Cayman 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 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 May 28, 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 May 28, 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
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
7.9
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
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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 May 28, 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 May 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$608 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$438 | Average$675 | FlexibilityNo cancel fee | On-time71% |