$123+ 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 6/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
May 9 — May 161
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 April 9, 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 April 9, 2026.
This Air Canada deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 6/101:55 pm
ORD
- GCM
2 stops21h 30m
Air Canada
Sat 6/1310:55 am
GCM
- ORD
1 stop22h 05m
Air Canada
Deal found 4/6![Air Canada logo]()
$350
This Orbitz deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 6/66:22 pm
ORD
- GCM
2 stops41h 03m
Air Canada
Sat 6/1310:55 am
GCM
- ORD
1 stop22h 05m
Air Canada
Deal found 4/6![Air Canada logo]()
$355
This Expedia deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 stop25h 00m
Air Canada
Deal found 4/8![Air Canada logo]()
$365
This FlightHub deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/298:35 pm
ORD
- GCM
1 stop13h 25m
Air Canada
Thu 6/412:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 4/4![Air Canada logo]()
$373
This Expedia deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
ORD
- GCM
1 stop7h 52m
Multiple Airlines
Tue 4/1412:30 pm
GCM
- ORD
1 stop24h 35m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$405
This Expedia deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/179:55 am
ORD
- GCM
1 stop25h 30m
Air Canada
Thu 5/2112:25 pm
GCM
- ORD
1 stop26h 30m
Air Canada
Deal found 4/6![Air Canada logo]()
$406
This Travelocity deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Wed 10/213:45 pm
ORD
- GCM
1 stop19h 45m
Air Canada
Sun 10/2512:25 pm
GCM
- ORD
1 stop24h 31m
Air Canada
Deal found 4/5![Air Canada logo]()
$407
This Orbitz deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Tue 6/96:22 pm
ORD
- GCM
2 stops41h 03m
Air Canada
Sat 6/2010:55 am
GCM
- ORD
2 stops20h 55m
Air Canada
Deal found 4/5![Air Canada logo]()
$408
This Expedia deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/97:55 am
ORD
- GCM
1 stop26h 15m
Multiple Airlines
Sat 4/111:15 pm
GCM
- ORD
1 stop6h 36m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$409
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:00 am
MDW
- GCM
2 stops10h 05m
Multiple Airlines
Sat 6/131:45 pm
GCM
- MDW
1 stop19h 55m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$547
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 am
MDW
- GCM
1 stop6h 10m
Southwest
Tue 5/261:05 pm
GCM
- MDW
1 stop8h 20m
Southwest
Deal found 4/6![Southwest logo]()
$551
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Mon 6/86:00 am
MDW
- GCM
2 stops15h 15m
Multiple Airlines
Sat 6/131:45 pm
GCM
- MDW
1 stop19h 55m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$567
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 April 9, 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 April 9, 2026.
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 am
MDW
- GCM
1 stop6h 10m
Southwest
Tue 5/261:05 pm
GCM
- MDW
1 stop8h 20m
Southwest
Deal found 4/6![Southwest logo]()
$551
This United Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/209:29 am
ORD
- GCM
Nonstop4h 01m
United Airlines
Tue 6/301:35 pm
GCM
- ORD
1 stop8h 05m
United Airlines
Deal found 4/8![United Airlines logo]()
$604
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 8/236:00 am
MDW
- GCM
1 stop5h 41m
Delta
Fri 8/2812:56 pm
GCM
- MDW
1 stop8h 50m
Delta
Deal found 4/5![Delta logo]()
$611
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/65:55 am
ORD
- GCM
1 stop6h 15m
Southwest
Wed 5/131:05 pm
GCM
- ORD
1 stop8h 50m
Southwest
Deal found 4/6![Southwest logo]()
$575
This Delta deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/205:30 am
ORD
- GCM
1 stop6h 04m
Delta
Sat 6/2712:59 pm
GCM
- ORD
1 stop7h 33m
Delta
Deal found 4/8![Delta logo]()
$623
This United Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/99:29 am
ORD
- GCM
Nonstop4h 01m
United Airlines
Sat 5/161:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 4/4![United Airlines logo]()
$631
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/75:10 am
MDW
- GCM
1 stop6h 40m
Southwest
Tue 7/1412:45 pm
GCM
- MDW
1 stop7h 30m
Southwest
Deal found 4/7![Southwest logo]()
$590
This Delta deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/95:15 am
ORD
- GCM
1 stop6h 16m
Delta
Mon 7/1312:56 pm
GCM
- ORD
1 stop9h 12m
Delta
Deal found 4/8![Delta logo]()
$623
This United Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/209:29 am
ORD
- GCM
Nonstop4h 01m
United Airlines
Sat 6/274:45 pm
GCM
- ORD
1 stop8h 00m
United Airlines
Deal found 4/8![United Airlines logo]()
$639
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/37:43 pm
ORD
- GCM
2 stops16h 17m
Delta
Sat 5/301:19 pm
GCM
- ORD
2 stops19h 26m
Delta
Deal found 4/4![Delta logo]()
$625
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:45 am
MDW
- GCM
2 stops7h 15m
Southwest
Sat 5/91:05 pm
GCM
- MDW
2 stops9h 40m
Southwest
Deal found 4/9![Southwest logo]()
$632
This United Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 6/279:29 am
ORD
- GCM
Nonstop4h 01m
United Airlines
Sat 7/41:35 pm
GCM
- ORD
1 stop9h 40m
United Airlines
Deal found 4/6![United Airlines logo]()
$639
This United Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 8/19:29 am
ORD
- GCM
Nonstop4h 01m
United Airlines
Fri 8/71:35 pm
GCM
- ORD
1 stop11h 10m
United Airlines
Deal found 4/4![United Airlines logo]()
$642
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/195:55 am
ORD
- GCM
1 stop6h 15m
Southwest
Tue 5/261:05 pm
GCM
- ORD
1 stop8h 50m
Southwest
Deal found 4/6![Southwest logo]()
$645
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/96:23 am
MDW
- GCM
1 stop5h 31m
Delta
Sat 5/161:19 pm
GCM
- MDW
1 stop7h 50m
Delta
Deal found 4/4![Delta logo]()
$645
This Delta deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
MDW
- GCM
1 stop5h 41m
Delta
Wed 8/2612:56 pm
GCM
- MDW
1 stop8h 50m
Delta
Deal found 4/8![Delta logo]()
$646
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/306:23 am
MDW
- GCM
1 stop5h 31m
Delta
Fri 6/51:19 pm
GCM
- MDW
1 stop7h 50m
Delta
Deal found 4/5![Delta logo]()
$653
Last-minute flights from Chicago to Grand CaymanDiscover last-minute flight deals from Chicago to Grand Cayman. Data last updated April 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Grand Cayman. Data last updated April 9, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/97:55 am
ORD
- GCM
1 stop26h 15m
Multiple Airlines
Sat 4/111:15 pm
GCM
- ORD
1 stop6h 36m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$409
This Expedia deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
ORD
- GCM
1 stop7h 52m
Multiple Airlines
Tue 4/1412:30 pm
GCM
- ORD
1 stop24h 35m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$405
This Air Canada deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/123:45 pm
ORD
- GCM
2 stops18h 30m
Air Canada
Tue 4/1412:30 pm
GCM
- ORD
2 stops19h 28m
Air Canada
Deal found 4/8![Air Canada logo]()
$441
This Air Canada deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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.
Mon 4/139:50 am
ORD
- GCM
1 stop25h 20m
Air Canada
Thu 4/1611:55 am
GCM
- ORD
1 stop21h 15m
Air Canada
Deal found 4/4![Air Canada logo]()
$418
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/226:00 am
MDW
- GCM
1 stop6h 10m
Southwest
Wed 4/291:05 pm
GCM
- MDW
1 stop6h 40m
Southwest
Deal found 4/6![Southwest logo]()
$595
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/45:35 am
MDW
- GCM
1 stop6h 35m
Southwest
Sun 5/1012:50 pm
GCM
- MDW
1 stop6h 20m
Southwest
Deal found 4/7![Southwest logo]()
$584
This Expedia deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/179:55 am
ORD
- GCM
1 stop25h 30m
Air Canada
Thu 5/2112:25 pm
GCM
- ORD
1 stop26h 30m
Air Canada
Deal found 4/6![Air Canada logo]()
$406
This Mytrip deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/179:55 am
ORD
- GCM
1 stop25h 30m
Multiple Airlines
Fri 5/225:05 pm
GCM
- ORD
1 stop6h 51m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$434
This Mytrip deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/178:35 pm
ORD
- GCM
1 stop14h 50m
Multiple Airlines
Thu 5/214:45 pm
GCM
- ORD
1 stop7h 11m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$448
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 am
MDW
- GCM
1 stop6h 10m
Southwest
Tue 5/261:05 pm
GCM
- MDW
1 stop8h 20m
Southwest
Deal found 4/6![Southwest logo]()
$551
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 am
MDW
- GCM
1 stop6h 10m
Southwest
Sun 5/3112:50 pm
GCM
- MDW
2 stops10h 50m
Southwest
Deal found 4/5![Southwest logo]()
$570
This FlightHub deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/298:35 pm
ORD
- GCM
1 stop13h 25m
Air Canada
Thu 6/412:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 4/4![Air Canada logo]()
$373
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 April 9, 2026.
Search for one-way flight options from Chicago to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated April 9, 2026.
This Travelocity deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 6/58:20 pm
ORD
- GCM
1 stop13h 40m
Air Canada
Deal found 4/6![Air Canada logo]()
$123
This Air Canada deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 6/31:55 pm
ORD
- GCM
2 stops21h 30m
Air Canada
Deal found 4/6![Air Canada logo]()
$128
This Air Canada deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 6/66:04 pm
ORD
- GCM
2 stops41h 21m
Air Canada
Deal found 4/6![Air Canada logo]()
$131
This Orbitz deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/78:20 pm
ORD
- GCM
1 stop15h 05m
Air Canada
Deal found 4/8![Air Canada logo]()
$133
This Travelocity deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/69:55 am
ORD
- GCM
1 stop25h 30m
Air Canada
Deal found 4/7![Air Canada logo]()
$141
This Expedia deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Tue 5/58:45 am
ORD
- GCM
2 stops50h 40m
Air Canada
Deal found 4/6![Air Canada logo]()
$144
This Air Canada deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/23:40 pm
ORD
- GCM
2 stops43h 45m
Air Canada
Deal found 4/6![Air Canada logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Thu 5/75:45 pm
ORD
- GCM
1 stop27h 50m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$150
This Travelocity deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 10/49:50 am
ORD
- GCM
1 stop25h 40m
Air Canada
Deal found 4/5![Air Canada logo]()
$154
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1312:04 pm
MDW
- GCM
2 stops23h 31m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$191
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/235:10 am
MDW
- GCM
1 stop6h 40m
Southwest
Deal found 4/7![Southwest logo]()
$237
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1611:59 am
MDW
- GCM
2 stops33h 36m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$259
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 April 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $350 (Air Canada) |
One-way from | $123 (Travelocity) |
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 April 9, 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
MDW - GCM
MDWGCM
Chicago Midway
Tue 5/19
6:00 am-12:10 pm
1 stop6h 10m
George Town Owen Roberts Intl
Tue 5/26
1:05 pm-9:25 pm
1 stop8h 20m
$551
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 5/6
5:55 am-12:10 pm
1 stop6h 15m
George Town Owen Roberts Intl
Wed 5/13
1:05 pm-9:55 pm
1 stop8h 50m
$575
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Tue 7/7
5:10 am-11:50 am
1 stop6h 40m
George Town Owen Roberts Intl
Tue 7/14
12:45 pm-8:15 pm
1 stop7h 30m
$590
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 6/20
9:29 am-1:30 pm
Nonstop4h 01m
George Town Owen Roberts Intl
Tue 6/30
1:35 pm-9:40 pm
1 stop8h 05m
$604
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Sun 8/23
6:00 am-11:41 am
1 stop5h 41m
George Town Owen Roberts Intl
Fri 8/28
12:56 pm-9:46 pm
1 stop8h 50m
$611
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 6/20
5:30 am-11:34 am
1 stop6h 04m
George Town Owen Roberts Intl
Sat 6/27
12:59 pm-8:32 pm
1 stop7h 33m
$623
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Thu 7/9
5:15 am-11:31 am
1 stop6h 16m
George Town Owen Roberts Intl
Mon 7/13
12:56 pm-10:08 pm
1 stop9h 12m
$623
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 5/3
7:43 pm-12:00 pm
2 stops16h 17m
George Town Owen Roberts Intl
Sat 5/30
1:19 pm-8:45 am
2 stops19h 26m
$625
Quickest round-trip
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 5/9
9:29 am-1:30 pm
Nonstop4h 01m
George Town Owen Roberts Intl
Sat 5/16
1:50 pm-6:13 pm
Nonstop4h 23m
$631
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Sat 5/2
7:45 am-3:00 pm
2 stops7h 15m
George Town Owen Roberts Intl
Sat 5/9
1:05 pm-10:45 pm
2 stops9h 40m
$632
Showing 1-10 of 37 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 April 9, 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 April 9, 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.
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
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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Chicago and Grand Cayman flights
Browse other Chicago and Grand Cayman flight options. Last updated on April 9, 2026.
Popular flight searches
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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 April 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$604 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$429 | Average$669 | FlexibilityNo cancel fee | On-time71% |