$75+ 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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Mar 13 — Mar 201
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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
Cheapest
Best
Last-minute
One-way
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 February 11, 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 February 11, 2026.
This Southwest deal was found by Cheapflights users on 2/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/19:35 pm
MDW
- GCM
2 stops14h 20m
Southwest
Tue 3/1012:40 pm
GCM
- MDW
2 stops10h 10m
Southwest
Deal found 2/8![Southwest logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/189:28 am
ORD
- GCM
2 stops27h 29m
Multiple Airlines
Wed 3/2511:30 am
GCM
- ORD
1 stop20h 55m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$379
This FlightHub deal was found by Cheapflights users on 2/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/145:05 am
ORD
- GCM
1 stop7h 15m
Spirit Airlines
Thu 3/191:52 pm
GCM
- ORD
1 stop9h 25m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$380
This Air Canada deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/44:15 pm
ORD
- GCM
1 stop18h 40m
Air Canada
Thu 4/911:55 am
GCM
- ORD
1 stop7h 30m
Air Canada
Deal found 2/10![Air Canada logo]()
$382
This Mytrip deal was found by Cheapflights users on 2/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1110:44 am
ORD
- GCM
3 stops26h 13m
Multiple Airlines
Wed 3/1811:30 am
GCM
- ORD
1 stop7h 01m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Thu 3/56:15 am
MDW
- GCM
1 stop14h 00m
Multiple Airlines
Thu 3/127:00 am
GCM
- MDW
1 stop6h 41m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$387
This Mytrip deal was found by Cheapflights users on 2/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/289:18 am
ORD
- GCM
3 stops27h 25m
Multiple Airlines
Mon 3/94:45 pm
GCM
- ORD
1 stop16h 54m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$391
This Mytrip deal was found by Cheapflights users on 2/8. 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.
Sat 2/288:16 pm
ORD
- GCM
1 stop16h 27m
Multiple Airlines
Wed 3/411:30 am
GCM
- ORD
2 stops21h 24m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:31 am
ORD
- GCM
1 stop11h 29m
Multiple Airlines
Tue 5/1911:30 am
GCM
- ORD
1 stop6h 45m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/225:15 am
ORD
- GCM
1 stop7h 28m
Multiple Airlines
Wed 2/2511:30 am
GCM
- ORD
1 stop23h 09m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$396
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/164:51 pm
ORD
- GCM
1 stop23h 14m
Multiple Airlines
Fri 3/208:00 am
GCM
- ORD
1 stop16h 22m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Tue 3/176:00 am
MDW
- GCM
2 stops10h 05m
Multiple Airlines
Mon 3/237:00 am
GCM
- MDW
1 stop6h 41m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$406
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 February 11, 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 February 11, 2026.
This Southwest deal was found by Cheapflights users on 2/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/19:35 pm
MDW
- GCM
2 stops14h 20m
Southwest
Tue 3/1012:40 pm
GCM
- MDW
1 stop6h 40m
Southwest
Deal found 2/8![Southwest logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Tue 3/176:00 am
MDW
- GCM
2 stops10h 05m
Multiple Airlines
Mon 3/237:00 am
GCM
- MDW
1 stop6h 41m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$406
This Delta deal was found by Cheapflights users on 2/8. 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.
Sun 2/226:00 am
MDW
- GCM
1 stop5h 29m
Delta
Wed 2/251:54 pm
GCM
- MDW
1 stop9h 37m
Delta
Deal found 2/8![Delta logo]()
$487
This Mytrip deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:01 pm
ORD
- GCM
3 stops18h 56m
Spirit Airlines
Sun 3/221:52 pm
GCM
- ORD
2 stops21h 58m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$495
This United Airlines deal was found by Cheapflights users on 2/8. 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.
Mon 3/168:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Fri 3/201:25 pm
GCM
- ORD
1 stop9h 48m
United Airlines
Deal found 2/8![United Airlines logo]()
$501
This American Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/99:45 am
ORD
- GCM
Nonstop3h 59m
American Airlines
Thu 3/122:44 pm
GCM
- ORD
Nonstop4h 10m
American Airlines
Deal found 2/10![American Airlines logo]()
$501
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:34 pm
ORD
- GCM
1 stop21h 31m
Multiple Airlines
Tue 6/211:30 am
GCM
- ORD
1 stop6h 45m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$409
This Southwest deal was found by Cheapflights users on 2/9. 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.
Fri 4/174:10 pm
MDW
- GCM
2 stops22h 30m
Southwest
Tue 4/211:05 pm
GCM
- MDW
2 stops10h 00m
Southwest
Deal found 2/9![Southwest logo]()
$464
This American Airlines deal was found by Cheapflights users on 2/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/249:36 am
ORD
- GCM
Nonstop3h 59m
American Airlines
Sat 2/284:00 pm
GCM
- ORD
Nonstop4h 20m
American Airlines
Deal found 2/9![American Airlines logo]()
$503
This Delta deal was found by Cheapflights users on 2/8. 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.
Wed 3/186:00 am
MDW
- GCM
1 stop5h 47m
Delta
Wed 3/251:12 pm
GCM
- MDW
1 stop9h 19m
Delta
Deal found 2/8![Delta logo]()
$505
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:35 am
MDW
- GCM
1 stop6h 35m
Southwest
Sat 4/181:05 pm
GCM
- MDW
1 stop9h 10m
Southwest
Deal found 2/10![Southwest logo]()
$473
This Delta deal was found by Cheapflights users on 2/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/265:10 am
ORD
- GCM
1 stop6h 50m
Delta
Wed 4/291:25 pm
GCM
- ORD
1 stop6h 51m
Delta
Deal found 2/7![Delta logo]()
$505
This Mytrip deal was found by Cheapflights users on 2/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/86:51 pm
ORD
- GCM
3 stops26h 24m
Multiple Airlines
Sat 3/141:15 pm
GCM
- ORD
1 stop6h 36m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$507
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:00 am
MDW
- GCM
1 stop6h 00m
Delta
Tue 4/281:25 pm
GCM
- MDW
1 stop9h 03m
Delta
Deal found 2/10![Delta logo]()
$515
This Southwest deal was found by Cheapflights users on 2/9. 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.
Sun 3/86:05 am
MDW
- GCM
1 stop5h 55m
Southwest
Sat 3/1411:20 am
GCM
- MDW
1 stop8h 50m
Southwest
Deal found 2/9![Southwest logo]()
$523
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
ORD
- GCM
1 stop5h 54m
Delta
Tue 5/191:19 pm
GCM
- ORD
1 stop9h 09m
Delta
Deal found 2/10![Delta logo]()
$515
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/119:20 am
MDW
- GCM
1 stop5h 20m
Southwest
Thu 4/161:05 pm
GCM
- MDW
1 stop10h 35m
Southwest
Deal found 2/10![Southwest logo]()
$523
Last-minute flights from Chicago to Grand CaymanDiscover last-minute flight deals from Chicago to Grand Cayman. Data last updated February 11, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Grand Cayman. Data last updated February 11, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/184:43 pm
ORD
- GCM
1 stop20h 00m
Multiple Airlines
Tue 2/2411:30 am
GCM
- ORD
1 stop23h 09m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$392
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/225:15 am
ORD
- GCM
1 stop7h 28m
Multiple Airlines
Wed 2/2511:30 am
GCM
- ORD
1 stop23h 09m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$396
This Mytrip deal was found by Cheapflights users on 2/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/289:18 am
ORD
- GCM
3 stops27h 25m
Multiple Airlines
Mon 3/94:45 pm
GCM
- ORD
1 stop16h 54m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$391
This Mytrip deal was found by Cheapflights users on 2/8. 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.
Sat 2/288:16 pm
ORD
- GCM
1 stop16h 27m
Multiple Airlines
Wed 3/411:30 am
GCM
- ORD
2 stops21h 24m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$393
This Southwest deal was found by Cheapflights users on 2/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/19:35 pm
MDW
- GCM
2 stops14h 20m
Southwest
Tue 3/1012:40 pm
GCM
- MDW
2 stops10h 10m
Southwest
Deal found 2/8![Southwest logo]()
$364
This Mytrip deal was found by Cheapflights users on 2/8. 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.
Mon 3/26:51 pm
ORD
- GCM
3 stops20h 14m
Multiple Airlines
Thu 3/52:49 pm
GCM
- ORD
1 stop7h 24m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Thu 3/56:15 am
MDW
- GCM
1 stop14h 00m
Multiple Airlines
Thu 3/127:00 am
GCM
- MDW
1 stop6h 41m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$387
This Mytrip deal was found by Cheapflights users on 2/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1110:44 am
ORD
- GCM
3 stops26h 13m
Multiple Airlines
Wed 3/1811:30 am
GCM
- ORD
1 stop7h 01m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$385
This FlightHub deal was found by Cheapflights users on 2/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/145:05 am
ORD
- GCM
1 stop7h 15m
Spirit Airlines
Thu 3/191:52 pm
GCM
- ORD
1 stop9h 25m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$380
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/164:51 pm
ORD
- GCM
1 stop23h 14m
Multiple Airlines
Fri 3/208:00 am
GCM
- ORD
1 stop16h 22m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/189:28 am
ORD
- GCM
2 stops27h 29m
Multiple Airlines
Wed 3/2511:30 am
GCM
- ORD
1 stop20h 55m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$379
This FlightHub deal was found by Cheapflights users on 2/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/307:04 am
ORD
- GCM
1 stop28h 06m
Air Canada
Mon 4/611:25 am
GCM
- ORD
1 stop25h 40m
Air Canada
Deal found 2/8![Air Canada logo]()
$382
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 February 11, 2026.
Search for one-way flight options from Chicago to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated February 11, 2026.
This FlightHub deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:05 am
ORD
- GCM
1 stop7h 15m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$75
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/61:27 pm
ORD
- GCM
1 stop23h 16m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$86
This FlightHub deal was found by Cheapflights users on 2/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/55:15 am
ORD
- GCM
1 stop7h 28m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:36 pm
ORD
- GCM
1 stop18h 21m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 4/86:10 pm
ORD
- GCM
1 stop18h 47m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/48:16 pm
ORD
- GCM
1 stop16h 27m
Spirit Airlines
Deal found 2/8![Spirit Airlines logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:17 am
ORD
- GCM
1 stop29h 03m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$99
This FlightHub deal was found by Cheapflights users on 2/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/78:16 pm
ORD
- GCM
1 stop15h 27m
Spirit Airlines
Deal found 2/8![Spirit Airlines logo]()
$102
This Trip.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/93:52 pm
ORD
- GCM
1 stop19h 43m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$108
This FlightHub deal was found by Cheapflights users on 2/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:15 am
ORD
- GCM
1 stop7h 28m
Spirit Airlines
Deal found 2/7![Spirit Airlines logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/125:05 am
ORD
- GCM
1 stop7h 52m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$117
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:20 pm
MDW
- GCM
2 stops16h 50m
Southwest
Deal found 2/10![Southwest logo]()
$127
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 February 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $364 (Southwest) |
One-way from | $75 (FlightHub) |
Popular in | December |
Cheapest in | February |
Average price | $527 |
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 February 11, 2026.
Use the filters below to find and compare flights from Chicago to Grand Cayman that are best for you.
Fly from
Chicago
Fly to
Grand Cayman
Route
Depart
Return
Price
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Sun 3/1
9:35 pm-12:55 pm
2 stops14h 20m
George Town Owen Roberts Intl
Tue 3/10
12:40 pm-7:20 pm
1 stop6h 40m
$364
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Tue 3/17
6:00 am-4:05 pm
2 stops10h 05m
George Town Owen Roberts Intl
Mon 3/23
7:00 am-1:41 pm
1 stop6h 41m
$406
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 5/26
6:34 pm-4:05 pm
1 stop21h 31m
George Town Owen Roberts Intl
Tue 6/2
11:30 am-6:15 pm
1 stop6h 45m
$409
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Fri 4/17
4:10 pm-2:40 pm
2 stops22h 30m
George Town Owen Roberts Intl
Tue 4/21
1:05 pm-11:05 pm
2 stops10h 00m
$464
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Mon 4/13
5:35 am-12:10 pm
1 stop6h 35m
George Town Owen Roberts Intl
Sat 4/18
1:05 pm-10:15 pm
1 stop9h 10m
$473
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Sun 2/22
6:00 am-12:29 pm
1 stop5h 29m
George Town Owen Roberts Intl
Wed 2/25
1:54 pm-10:31 pm
1 stop9h 37m
$487
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 3/18
6:01 pm-12:57 pm
3 stops18h 56m
George Town Owen Roberts Intl
Sun 3/22
1:52 pm-11:50 am
2 stops21h 58m
$495
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Mon 3/16
8:45 am-12:45 pm
Nonstop4h 00m
George Town Owen Roberts Intl
Fri 3/20
1:25 pm-11:13 pm
1 stop9h 48m
$501
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Mon 3/9
9:45 am-1:44 pm
Nonstop3h 59m
George Town Owen Roberts Intl
Thu 3/12
2:44 pm-6:54 pm
Nonstop4h 10m
$501
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 2/24
9:36 am-2:35 pm
Nonstop3h 59m
George Town Owen Roberts Intl
Sat 2/28
4:00 pm-7:20 pm
Nonstop4h 20m
$503
Showing 1-10 of 31 results
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 $659). 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 February 11, 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 February 11, 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
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Alternative routes for Chicago to Grand Cayman
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Grand Cayman by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Grand Cayman by cabin class
Find flights from Chicago to Grand Cayman, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Grand Cayman flights
Browse other Chicago and Grand Cayman flight options. Last updated on February 11, 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 February 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$617 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$438 | Average$677 | FlexibilityNo cancel fee | On-time71% |