$133+ 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 6/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
May 27 — Jun 31
Round-trip
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 April 27, 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 27, 2026.
This Orbitz deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/79:55 am
ORD
- GCM
1 stop25h 30m
Air Canada
Thu 6/1112:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 4/23![Air Canada logo]()
$365
This Air Canada deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:20 pm
ORD
- GCM
1 stop13h 40m
Air Canada
Mon 6/1512:25 pm
GCM
- ORD
1 stop26h 30m
Air Canada
Deal found 4/23![Air Canada logo]()
$375
This Orbitz deal was found by Cheapflights users on 4/27. 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 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
Mon 6/1512:25 pm
GCM
- ORD
2 stops46h 55m
Air Canada
Deal found 4/27![Air Canada logo]()
$379
This Gotogate deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/79:55 am
ORD
- GCM
1 stop25h 30m
Multiple Airlines
Fri 6/127:00 am
GCM
- ORD
2 stops31h 55m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$399
This Orbitz deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:05 am
ORD
- GCM
2 stops48h 25m
Air Canada
Sat 9/1912:25 pm
GCM
- ORD
1 stop24h 58m
Air Canada
Deal found 4/25![Air Canada logo]()
$417
This Expedia deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:21 pm
ORD
- GCM
2 stops41h 04m
Air Canada
Sat 9/1212:25 pm
GCM
- ORD
2 stops19h 19m
Air Canada
Deal found 4/23![Air Canada logo]()
$423
This Air Canada deal was found by Cheapflights users on 4/27. 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.
Fri 6/128:20 pm
ORD
- GCM
1 stop13h 40m
Air Canada
Mon 6/2212:25 pm
GCM
- ORD
2 stops19h 25m
Air Canada
Deal found 4/27![Air Canada logo]()
$424
This Air Canada deal was found by Cheapflights users on 4/26. 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.
Fri 6/51:55 pm
ORD
- GCM
2 stops20h 05m
Air Canada
Sat 6/1310:55 am
GCM
- ORD
2 stops31h 52m
Air Canada
Deal found 4/26![Air Canada logo]()
$425
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/76:05 am
MDW
- GCM
1 stop5h 29m
Delta
Fri 6/1212:59 pm
GCM
- MDW
1 stop9h 18m
Delta
Deal found 4/23![Delta logo]()
$481
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:30 am
MDW
- GCM
2 stops25h 55m
Delta
Thu 11/121:50 pm
GCM
- MDW
2 stops19h 55m
Delta
Deal found 4/23![Delta logo]()
$486
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
MDW
- GCM
1 stop5h 41m
Delta
Wed 8/2612:56 pm
GCM
- MDW
1 stop8h 50m
Delta
Deal found 4/22![Delta logo]()
$581
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:30 am
MDW
- GCM
2 stops25h 55m
Delta
Sat 11/141:50 pm
GCM
- MDW
1 stop8h 55m
Delta
Deal found 4/23![Delta logo]()
$586
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 27, 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 27, 2026.
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/75:30 am
ORD
- GCM
1 stop6h 04m
Delta
Fri 6/1212:59 pm
GCM
- ORD
1 stop9h 14m
Delta
Deal found 4/23![Delta logo]()
$481
This Southwest deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/115:35 am
MDW
- GCM
1 stop6h 35m
Southwest
Thu 5/141:05 pm
GCM
- MDW
1 stop11h 10m
Southwest
Deal found 4/24![Southwest logo]()
$667
This Trip.com deal was found by Cheapflights users on 4/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:00 am
MDW
- GCM
2 stops15h 15m
Multiple Airlines
Sat 5/168:50 am
GCM
- MDW
2 stops13h 12m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$667
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/295:15 am
ORD
- GCM
1 stop6h 16m
Delta
Sun 8/212:56 pm
GCM
- ORD
1 stop9h 12m
Delta
Deal found 4/23![Delta logo]()
$581
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/55:30 am
ORD
- GCM
1 stop6h 24m
Delta
Tue 6/912:59 pm
GCM
- ORD
1 stop11h 00m
Delta
Deal found 4/22![Delta logo]()
$599
This Southwest deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/109:05 pm
MDW
- GCM
2 stops14h 45m
Southwest
Mon 6/1512:45 pm
GCM
- MDW
2 stops11h 10m
Southwest
Deal found 4/22![Southwest logo]()
$672
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:30 am
ORD
- GCM
1 stop6h 24m
Delta
Tue 6/912:59 pm
GCM
- ORD
1 stop7h 33m
Delta
Deal found 4/23![Delta logo]()
$599
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:00 am
MDW
- GCM
1 stop7h 05m
Southwest
Sat 9/121:00 pm
GCM
- MDW
2 stops16h 40m
Southwest
Deal found 4/25![Southwest logo]()
$679
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/67:59 pm
ORD
- GCM
1 stop15h 32m
Delta
Sun 8/212:56 pm
GCM
- ORD
1 stop9h 12m
Delta
Deal found 4/22![Delta logo]()
$599
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/15:30 am
ORD
- GCM
1 stop6h 24m
Delta
Sat 6/61:19 pm
GCM
- ORD
1 stop8h 34m
Delta
Deal found 4/22![Delta logo]()
$599
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:00 pm
ORD
- GCM
2 stops16h 54m
Delta
Fri 6/1212:59 pm
GCM
- ORD
1 stop11h 00m
Delta
Deal found 4/23![Delta logo]()
$604
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/145:30 am
ORD
- GCM
1 stop6h 04m
Delta
Sun 6/2112:59 pm
GCM
- ORD
1 stop11h 00m
Delta
Deal found 4/24![Delta logo]()
$606
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/165:30 am
ORD
- GCM
1 stop6h 11m
Delta
Fri 8/2112:56 pm
GCM
- ORD
1 stop8h 24m
Delta
Deal found 4/25![Delta logo]()
$611
This Delta deal was found by Cheapflights users on 4/26. 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.
Tue 7/285:30 am
ORD
- GCM
1 stop6h 01m
Delta
Wed 8/512:56 pm
GCM
- ORD
1 stop7h 37m
Delta
Deal found 4/26![Delta logo]()
$611
This Delta deal was found by Cheapflights users on 4/26. 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.
Sun 7/265:18 pm
ORD
- GCM
2 stops18h 13m
Delta
Fri 7/3112:56 pm
GCM
- ORD
1 stop9h 12m
Delta
Deal found 4/26![Delta logo]()
$616
This Delta deal was found by Cheapflights users on 4/26. 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.
Mon 7/275:18 pm
ORD
- GCM
2 stops18h 13m
Delta
Tue 8/412:56 pm
GCM
- ORD
1 stop10h 57m
Delta
Deal found 4/26![Delta logo]()
$616
This Delta deal was found by Cheapflights users on 4/26. 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.
Sat 8/226:00 am
MDW
- GCM
1 stop5h 41m
Delta
Wed 8/2612:56 pm
GCM
- MDW
1 stop8h 50m
Delta
Deal found 4/26![Delta logo]()
$646
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:05 am
MDW
- GCM
1 stop5h 26m
Delta
Sat 8/1512:56 pm
GCM
- MDW
1 stop8h 50m
Delta
Deal found 4/25![Delta logo]()
$681
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:05 am
MDW
- GCM
1 stop5h 29m
Delta
Mon 6/1512:59 pm
GCM
- MDW
1 stop9h 18m
Delta
Deal found 4/22![Delta logo]()
$692
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:00 am
MDW
- GCM
1 stop5h 41m
Delta
Sat 9/1212:55 pm
GCM
- MDW
1 stop8h 51m
Delta
Deal found 4/23![Delta logo]()
$706
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:23 am
MDW
- GCM
1 stop5h 31m
Delta
Tue 6/912:59 pm
GCM
- MDW
1 stop9h 18m
Delta
Deal found 4/25![Delta logo]()
$706
Last-minute flights from Chicago to Grand CaymanDiscover last-minute flight deals from Chicago to Grand Cayman. Data last updated April 27, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Grand Cayman. Data last updated April 27, 2026 and is based on user searches.
This Travelocity deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/255:57 pm
ORD
- GCM
1 stop16h 58m
Multiple Airlines
Tue 4/283:05 pm
GCM
- ORD
1 stop16h 36m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$580
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/99:20 am
MDW
- GCM
1 stop5h 40m
Southwest
Tue 5/121:05 pm
GCM
- MDW
1 stop6h 40m
Southwest
Deal found 4/23![Southwest logo]()
$687
This Orbitz deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/109:55 am
ORD
- GCM
1 stop25h 30m
Multiple Airlines
Sat 5/162:20 pm
GCM
- ORD
1 stop17h 24m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$518
This Expedia deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/117:20 am
ORD
- GCM
2 stops29h 25m
JetBlue
Sat 5/162:20 pm
GCM
- ORD
1 stop17h 24m
JetBlue
Deal found 4/26![JetBlue logo]()
$587
This Southwest deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/115:35 am
MDW
- GCM
1 stop6h 35m
Southwest
Thu 5/141:05 pm
GCM
- MDW
1 stop11h 10m
Southwest
Deal found 4/24![Southwest logo]()
$667
This Air Canada deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:21 pm
ORD
- GCM
2 stops17h 04m
Air Canada
Mon 5/2512:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 4/25![Air Canada logo]()
$556
This Expedia deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:22 pm
ORD
- GCM
2 stops41h 03m
Air Canada
Sat 5/3010:55 am
GCM
- ORD
1 stop22h 55m
Air Canada
Deal found 4/23![Air Canada logo]()
$506
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2311:59 am
MDW
- GCM
2 stops23h 36m
Multiple Airlines
Sat 5/301:45 pm
GCM
- MDW
1 stop20h 00m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$581
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/231:50 pm
ORD
- GCM
2 stops21h 45m
Multiple Airlines
Sun 5/314:45 pm
GCM
- ORD
1 stop7h 11m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$594
This Gotogate deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/252:15 pm
ORD
- GCM
2 stops44h 10m
Multiple Airlines
Mon 6/112:25 pm
GCM
- ORD
1 stop28h 34m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$542
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Wed 5/271:50 pm
ORD
- GCM
2 stops21h 45m
Multiple Airlines
Sun 5/314:45 pm
GCM
- ORD
1 stop7h 11m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$585
This Air Canada deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/293:50 pm
ORD
- GCM
1 stop18h 10m
Air Canada
Mon 6/112:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 4/22![Air Canada logo]()
$475
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 27, 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 27, 2026.
This Orbitz deal was found by Cheapflights users on 4/27. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/248:40 pm
ORD
- GCM
1 stop14h 45m
Air Canada
Deal found 4/27![Air Canada logo]()
$133
This Expedia deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2311:05 am
ORD
- GCM
2 stops48h 20m
Air Canada
Deal found 4/24![Air Canada logo]()
$137
This Air Canada deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/218:40 pm
ORD
- GCM
1 stop14h 45m
Air Canada
Deal found 4/23![Air Canada logo]()
$138
This Air Canada deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/202:02 pm
ORD
- GCM
2 stops45h 23m
Air Canada
Deal found 4/23![Air Canada logo]()
$142
This Expedia deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:40 pm
ORD
- GCM
1 stop14h 50m
Air Canada
Deal found 4/25![Air Canada logo]()
$157
This Travelocity deal was found by Cheapflights users on 4/26. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:45 am
ORD
- GCM
2 stops50h 40m
Air Canada
Deal found 4/26![Air Canada logo]()
$161
This Air Canada deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2110:53 am
ORD
- GCM
2 stops24h 37m
Air Canada
Deal found 4/23![Air Canada logo]()
$162
This Expedia deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/108:40 pm
ORD
- GCM
1 stop13h 15m
Air Canada
Deal found 4/26![Air Canada logo]()
$183
This Expedia deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/238:45 am
ORD
- GCM
2 stops49h 15m
Air Canada
Deal found 4/24![Air Canada logo]()
$187
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:23 am
MDW
- GCM
1 stop5h 31m
Delta
Deal found 4/22![Delta logo]()
$188
This Air Canada deal was found by Cheapflights users on 4/27. 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 7/229:50 am
ORD
- GCM
1 stop25h 35m
Air Canada
Deal found 4/27![Air Canada logo]()
$188
This Travelocity deal was found by Cheapflights users on 4/26. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/249:55 am
ORD
- GCM
1 stop25h 30m
Air Canada
Deal found 4/26![Air Canada logo]()
$191
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 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $365 (Orbitz) |
One-way from | $133 (Orbitz) |
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 27, 2026.
Use the filters below to find and compare flights from Chicago to Grand Cayman that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 6/7
5:30 am-11:34 am
1 stop6h 04m
George Town Owen Roberts Intl
Fri 6/12
12:59 pm-10:13 pm
1 stop9h 14m
$481
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 7/29
5:15 am-11:31 am
1 stop6h 16m
George Town Owen Roberts Intl
Sun 8/2
12:56 pm-10:08 pm
1 stop9h 12m
$581
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Fri 6/5
5:30 am-11:54 am
1 stop6h 24m
George Town Owen Roberts Intl
Tue 6/9
12:59 pm-11:59 pm
1 stop11h 00m
$599
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 6/6
5:30 am-11:54 am
1 stop6h 24m
George Town Owen Roberts Intl
Tue 6/9
12:59 pm-8:32 pm
1 stop7h 33m
$599
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Mon 7/6
7:59 pm-11:31 am
1 stop15h 32m
George Town Owen Roberts Intl
Sun 8/2
12:56 pm-10:08 pm
1 stop9h 12m
$599
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Mon 6/1
5:30 am-11:54 am
1 stop6h 24m
George Town Owen Roberts Intl
Sat 6/6
1:19 pm-9:53 pm
1 stop8h 34m
$599
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Thu 6/4
7:00 pm-11:54 am
2 stops16h 54m
George Town Owen Roberts Intl
Fri 6/12
12:59 pm-11:59 pm
1 stop11h 00m
$604
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 6/14
5:30 am-11:34 am
1 stop6h 04m
George Town Owen Roberts Intl
Sun 6/21
12:59 pm-11:59 pm
1 stop11h 00m
$606
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 8/16
5:30 am-11:41 am
1 stop6h 11m
George Town Owen Roberts Intl
Fri 8/21
12:56 pm-9:20 pm
1 stop8h 24m
$611
Quickest round-trip
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 7/28
5:30 am-11:31 am
1 stop6h 01m
George Town Owen Roberts Intl
Wed 8/5
12:56 pm-8:33 pm
1 stop7h 37m
$611
Showing 1-10 of 42 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
How far ahead should I book a flight from Chicago to Grand Cayman?
Booking 1 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Grand Cayman. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Chicago to Grand Cayman?
Currently, December is the cheapest month in which you can book a flight from Chicago to Grand Cayman (average of $172). Flying from Chicago to Grand Cayman in September is currently the most expensive (average of $569). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to LAW?
Find hourly flight availability from Chicago to Grand Cayman. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 27, 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 27, 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.
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
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.
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.
Complete your trip
Flights by cabin class
Other flight options
Popular flights
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 April 27, 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 April 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$602 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$438 | Average$676 | FlexibilityNo cancel fee | On-time71% |