$109+ 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 3/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Apr 1 — Apr 81
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Grand Cayman
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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 March 2, 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 March 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 5/117:50 am
ORD
- GCM
1 stop13h 25m
Multiple Airlines
Mon 5/1812:40 pm
GCM
- ORD
1 stop11h 18m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$462
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:30 am
MDW
- GCM
1 stop14h 45m
Multiple Airlines
Mon 4/207:00 am
GCM
- MDW
2 stops12h 31m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$462
This Mytrip deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
Wed 3/1812:45 pm
ORD
- GCM
3 stops24h 12m
Multiple Airlines
Tue 3/2411:30 am
GCM
- ORD
2 stops21h 20m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$463
This Kiwi.com deal was found by Cheapflights users on 2/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
- GCM
1 stop28h 20m
Multiple Airlines
Thu 3/57:00 am
GCM
- MDW
1 stop7h 56m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$464
This Kiwi.com deal was found by Cheapflights users on 2/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/306:40 am
ORD
- GCM
2 stops8h 10m
Multiple Airlines
Fri 6/54:45 pm
GCM
- ORD
1 stop19h 24m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$465
This Air Canada deal was found by Cheapflights users on 2/26. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/268:40 pm
ORD
- GCM
1 stop14h 45m
Air Canada
Mon 3/3011:25 am
GCM
- ORD
1 stop10h 38m
Air Canada
Deal found 2/26![Air Canada logo]()
$466
This Kiwi.com deal was found by Cheapflights users on 2/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/103:52 pm
ORD
- GCM
1 stop29h 23m
Multiple Airlines
Sun 5/175:05 pm
GCM
- ORD
2 stops29h 34m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$468
This Mytrip deal was found by Cheapflights users on 2/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/147:31 pm
ORD
- GCM
2 stops17h 26m
Spirit Airlines
Sat 3/211:15 pm
GCM
- ORD
1 stop6h 36m
Spirit Airlines
Deal found 2/27![Spirit Airlines logo]()
$469
This Mytrip deal was found by Cheapflights users on 2/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/310:44 am
ORD
- GCM
3 stops28h 21m
Multiple Airlines
Thu 3/52:49 pm
GCM
- ORD
1 stop7h 24m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$470
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/67:40 am
ORD
- GCM
1 stop12h 55m
Multiple Airlines
Tue 3/1011:30 am
GCM
- ORD
1 stop22h 09m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$473
This Kiwi.com deal was found by Cheapflights users on 2/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/174:51 pm
ORD
- GCM
1 stop23h 14m
Multiple Airlines
Sun 3/298:00 am
GCM
- ORD
1 stop24h 01m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$474
This Air Canada deal was found by Cheapflights users on 2/27. 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 6/245:35 pm
ORD
- GCM
1 stop17h 55m
Air Canada
Sat 7/412:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 2/27![Air Canada logo]()
$475
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 March 2, 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 March 2, 2026.
This Delta deal was found by Cheapflights users on 2/27. 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.
Tue 4/215:15 am
ORD
- GCM
1 stop6h 45m
Delta
Tue 4/281:25 pm
GCM
- ORD
1 stop6h 51m
Delta
Deal found 2/27![Delta logo]()
$499
This Southwest deal was found by Cheapflights users on 2/26. 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 4/259:20 am
MDW
- GCM
1 stop5h 40m
Southwest
Wed 4/291:05 pm
GCM
- MDW
1 stop8h 20m
Southwest
Deal found 2/26![Southwest logo]()
$502
This United Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
Tue 4/148:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Wed 4/221:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/1![United Airlines logo]()
$521
This Southwest deal was found by Cheapflights users on 2/26. 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 5/86:00 am
ORD
- GCM
1 stop6h 10m
Southwest
Tue 5/121:05 pm
GCM
- ORD
1 stop8h 50m
Southwest
Deal found 2/26![Southwest logo]()
$516
This United Airlines deal was found by Cheapflights users on 2/26. 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.
Tue 3/245:40 am
ORD
- GCM
1 stop9h 50m
United Airlines
Tue 3/311:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 2/26![United Airlines logo]()
$525
This Delta deal was found by Cheapflights users on 2/26. 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 4/156:00 am
MDW
- GCM
1 stop6h 00m
Delta
Mon 4/201:25 pm
GCM
- MDW
1 stop9h 03m
Delta
Deal found 2/26![Delta logo]()
$529
This Southwest deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/158:50 pm
MDW
- GCM
2 stops15h 20m
Southwest
Mon 4/201:05 pm
GCM
- MDW
1 stop11h 00m
Southwest
Deal found 2/26![Southwest logo]()
$531
This United Airlines deal was found by Cheapflights users on 2/26. 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.
Wed 4/158:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Mon 4/201:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 2/26![United Airlines logo]()
$546
This Delta deal was found by Cheapflights users on 2/27. 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 8/176:00 am
MDW
- GCM
1 stop5h 41m
Delta
Fri 8/2112:56 pm
GCM
- MDW
1 stop8h 50m
Delta
Deal found 2/27![Delta logo]()
$571
This Southwest deal was found by Cheapflights users on 2/26. 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.
Tue 3/246:00 am
MDW
- GCM
1 stop5h 45m
Southwest
Tue 3/3111:50 am
GCM
- MDW
2 stops10h 05m
Southwest
Deal found 2/26![Southwest logo]()
$566
This United Airlines deal was found by Cheapflights users on 2/26. 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.
Thu 4/168:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Mon 4/201:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 2/26![United Airlines logo]()
$571
This Delta deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 8/16:00 am
MDW
- GCM
1 stop5h 42m
Delta
Fri 8/712:40 pm
GCM
- MDW
2 stops20h 02m
Delta
Deal found 3/2![Delta logo]()
$601
This Southwest deal was found by Cheapflights users on 2/26. 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.
Sun 7/128:40 pm
MDW
- GCM
2 stops15h 10m
Southwest
Thu 7/1612:45 pm
GCM
- MDW
1 stop8h 35m
Southwest
Deal found 2/26![Southwest logo]()
$588
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:00 am
ORD
- GCM
1 stop5h 26m
Delta
Sun 8/212:40 pm
GCM
- ORD
1 stop7h 38m
Delta
Deal found 2/28![Delta logo]()
$621
This United Airlines deal was found by Cheapflights users on 2/27. 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.
Mon 4/208:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Wed 4/291:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 2/27![United Airlines logo]()
$631
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 5/239:20 am
MDW
- GCM
1 stop5h 20m
Southwest
Wed 5/271:05 pm
GCM
- MDW
1 stop8h 20m
Southwest
Deal found 3/1![Southwest logo]()
$603
This United Airlines deal was found by Cheapflights users on 2/26. 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.
Sun 4/266:00 am
ORD
- GCM
1 stop7h 35m
United Airlines
Wed 4/291:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 2/26![United Airlines logo]()
$635
This United Airlines deal was found by Cheapflights users on 2/27. 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.
Tue 4/215:48 am
ORD
- GCM
1 stop6h 42m
United Airlines
Wed 4/291:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 2/27![United Airlines logo]()
$635
Last-minute flights from Chicago to Grand CaymanDiscover last-minute flight deals from Chicago to Grand Cayman. Data last updated March 2, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Grand Cayman. Data last updated March 2, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 2/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/310:44 am
ORD
- GCM
3 stops28h 21m
Multiple Airlines
Thu 3/52:49 pm
GCM
- ORD
1 stop7h 24m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$470
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/67:40 am
ORD
- GCM
1 stop12h 55m
Multiple Airlines
Tue 3/1011:30 am
GCM
- ORD
1 stop22h 09m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$473
This Mytrip deal was found by Cheapflights users on 2/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/147:31 pm
ORD
- GCM
2 stops17h 26m
Spirit Airlines
Sat 3/211:15 pm
GCM
- ORD
1 stop6h 36m
Spirit Airlines
Deal found 2/27![Spirit Airlines logo]()
$469
This Kiwi.com deal was found by Cheapflights users on 2/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/174:51 pm
ORD
- GCM
1 stop23h 14m
Multiple Airlines
Sun 3/298:00 am
GCM
- ORD
1 stop24h 01m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$474
This Mytrip deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
Wed 3/1812:45 pm
ORD
- GCM
3 stops24h 12m
Multiple Airlines
Tue 3/2411:30 am
GCM
- ORD
2 stops21h 20m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$463
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/239:53 am
ORD
- GCM
1 stop11h 22m
Multiple Airlines
Sun 3/295:05 pm
GCM
- ORD
2 stops31h 18m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$480
This Air Canada deal was found by Cheapflights users on 2/26. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/268:40 pm
ORD
- GCM
1 stop14h 45m
Air Canada
Mon 3/3011:25 am
GCM
- ORD
1 stop10h 38m
Air Canada
Deal found 2/26![Air Canada logo]()
$466
This FlightHub deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/309:15 pm
ORD
- GCM
1 stop13h 55m
Multiple Airlines
Mon 4/63:10 pm
GCM
- ORD
2 stops16h 58m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$476
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:30 am
MDW
- GCM
1 stop14h 45m
Multiple Airlines
Mon 4/207:00 am
GCM
- MDW
2 stops12h 31m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$462
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
Tue 4/144:51 pm
ORD
- GCM
1 stop23h 14m
Multiple Airlines
Wed 4/2211:30 am
GCM
- ORD
2 stops35h 09m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$477
This Kiwi.com deal was found by Cheapflights users on 2/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/177:50 am
ORD
- GCM
1 stop13h 45m
Multiple Airlines
Mon 4/207:00 am
GCM
- ORD
1 stop17h 55m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$478
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/197:20 pm
MDW
- GCM
2 stops16h 50m
Southwest
Thu 4/231:05 pm
GCM
- MDW
1 stop11h 00m
Southwest
Deal found 3/1![Southwest logo]()
$478
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 March 2, 2026.
Search for one-way flight options from Chicago to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated March 2, 2026.
This Expedia deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/197:17 am
ORD
- GCM
1 stop5h 40m
Spirit Airlines
Deal found 3/1![Spirit Airlines logo]()
$109
This FlightHub deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/55:05 am
ORD
- GCM
1 stop7h 52m
Spirit Airlines
Deal found 2/27![Spirit Airlines logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/18:10 am
ORD
- GCM
1 stop28h 47m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$126
This Air Canada deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/66:40 pm
ORD
- GCM
1 stop16h 30m
Air Canada
Deal found 3/1![Air Canada logo]()
$127
This Air Canada deal was found by Cheapflights users on 2/27. 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 4/264:43 pm
ORD
- GCM
1 stop17h 32m
Air Canada
Deal found 2/27![Air Canada logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 2/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:52 pm
ORD
- GCM
1 stop19h 43m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$131
This Air Canada deal was found by Cheapflights users on 2/27. 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 3/299:05 am
ORD
- GCM
1 stop25h 10m
Air Canada
Deal found 2/27![Air Canada logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 5/117:50 am
ORD
- GCM
1 stop13h 25m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 2/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/244:51 pm
ORD
- GCM
1 stop23h 14m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/254:36 pm
ORD
- GCM
1 stop20h 21m
Spirit Airlines
Deal found 3/1![Spirit Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 2/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/303:52 pm
ORD
- GCM
1 stop19h 43m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
Sun 3/156:00 am
MDW
- GCM
1 stop29h 35m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$145
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 March 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $462 (Kiwi.com) |
One-way from | $109 (Expedia) |
Popular in | December |
Cheapest in | February |
Average price | $685 |
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 March 2, 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
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 4/21
5:15 am-12:00 pm
1 stop6h 45m
George Town Owen Roberts Intl
Tue 4/28
1:25 pm-8:16 pm
1 stop6h 51m
$499
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Sat 4/25
9:20 am-3:00 pm
1 stop5h 40m
George Town Owen Roberts Intl
Wed 4/29
1:05 pm-9:25 pm
1 stop8h 20m
$502
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Fri 5/8
6:00 am-12:10 pm
1 stop6h 10m
George Town Owen Roberts Intl
Tue 5/12
1:05 pm-9:55 pm
1 stop8h 50m
$516
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 4/14
8:45 am-12:45 pm
Nonstop4h 00m
George Town Owen Roberts Intl
Wed 4/22
1:50 pm-6:13 pm
Nonstop4h 23m
$521
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 3/24
5:40 am-3:30 pm
1 stop9h 50m
George Town Owen Roberts Intl
Tue 3/31
1:50 pm-6:13 pm
Nonstop4h 23m
$525
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Wed 4/15
6:00 am-12:00 pm
1 stop6h 00m
George Town Owen Roberts Intl
Mon 4/20
1:25 pm-10:28 pm
1 stop9h 03m
$529
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Wed 4/15
8:50 pm-12:10 pm
2 stops15h 20m
George Town Owen Roberts Intl
Mon 4/20
1:05 pm-12:05 am
1 stop11h 00m
$531
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 4/15
8:45 am-12:45 pm
Nonstop4h 00m
George Town Owen Roberts Intl
Mon 4/20
1:50 pm-6:13 pm
Nonstop4h 23m
$546
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Tue 3/24
6:00 am-11:45 am
1 stop5h 45m
George Town Owen Roberts Intl
Tue 3/31
11:50 am-9:55 pm
2 stops10h 05m
$566
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Mon 8/17
6:00 am-11:41 am
1 stop5h 41m
George Town Owen Roberts Intl
Fri 8/21
12:56 pm-9:46 pm
1 stop8h 50m
$571
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.
MDW-GCM
ORD-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
MDW-GCM
ORD-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 March 2, 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.
Weekly flight availability from Chicago to Grand Cayman
Explore weekly flight availability from Chicago to Grand Cayman. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 2, 2026.
The most flights from CHI to zzLAW are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).
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 March 2, 2026.
Read reviews from past customers who have flown Southwest, Delta, and United 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
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
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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Chicago and Grand Cayman flights
Browse other Chicago and Grand Cayman flight options. Last updated on March 2, 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 March 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$610 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$438 | Average$669 | FlexibilityNo cancel fee | On-time71% |