$199+ Cheap flights from Grand Cayman to Illinois
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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — ORD
Mar 4 — Mar 111
1 adult, Economy
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Cheapest flights from Grand Cayman to IllinoisExplore the most affordable flight options available from Grand Cayman to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 2, 2026.
Explore the most affordable flight options available from Grand Cayman to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 2, 2026.
This Mytrip deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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.
Thu 2/192:49 pm
GCM
- ORD
1 stop7h 24m
Spirit Airlines
Wed 2/255:58 pm
ORD
- GCM
2 stops18h 45m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$316
This Mytrip deal was found by Cheapflights users on 2/1. 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.
Fri 4/1011:10 am
GCM
- ORD
1 stop8h 15m
Multiple Airlines
Sat 4/115:05 am
ORD
- GCM
1 stop7h 15m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” 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 3/1711:30 am
GCM
- ORD
1 stop20h 55m
Multiple Airlines
Tue 3/244:51 pm
ORD
- GCM
1 stop23h 14m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$363
This Expedia deal was found by Cheapflights users on 2/1. 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.
Fri 4/1011:10 am
GCM
- ORD
2 stops24h 27m
Air Canada
Sat 4/116:01 pm
ORD
- GCM
2 stops40h 14m
Air Canada
Deal found 2/1![Air Canada logo]()
$428
This American Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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.
Thu 2/193:35 pm
GCM
- ORD
Nonstop4h 10m
American Airlines
Wed 2/256:10 am
ORD
- GCM
1 stop8h 15m
American Airlines
Deal found 1/31![American Airlines logo]()
$453
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/191:50 pm
GCM
- MDW
1 stop9h 35m
Southwest
Wed 2/255:00 am
MDW
- GCM
1 stop6h 55m
Southwest
Deal found 1/31![Southwest logo]()
$495
This Delta deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” 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 3/171:12 pm
GCM
- MDW
1 stop9h 19m
Delta
Tue 3/246:00 am
MDW
- GCM
1 stop5h 47m
Delta
Deal found 1/30![Delta logo]()
$496
This Southwest deal was found by Cheapflights users on 2/1. 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.
Wed 4/112:20 pm
GCM
- MDW
2 stops11h 35m
Southwest
Mon 4/66:25 pm
MDW
- GCM
2 stops17h 45m
Southwest
Deal found 2/1![Southwest logo]()
$537
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/131:54 pm
GCM
- MDW
1 stop9h 37m
Delta
Wed 2/186:00 am
MDW
- GCM
1 stop5h 29m
Delta
Deal found 2/1![Delta logo]()
$540
This Southwest deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” 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 3/1712:40 pm
GCM
- MDW
1 stop6h 40m
Southwest
Tue 3/246:35 pm
MDW
- GCM
2 stops17h 10m
Southwest
Deal found 1/30![Southwest logo]()
$564
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/11:12 pm
GCM
- MDW
1 stop9h 19m
Delta
Mon 4/66:00 am
MDW
- GCM
1 stop5h 47m
Delta
Deal found 2/1![Delta logo]()
$1,682
Best flights from Grand Cayman to IllinoisDiscover carefully curated flight deals from Grand Cayman to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 2, 2026.
Discover carefully curated flight deals from Grand Cayman to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 2, 2026.
This Mytrip deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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.
Thu 2/192:49 pm
GCM
- ORD
1 stop7h 24m
Spirit Airlines
Wed 2/255:58 pm
ORD
- GCM
2 stops18h 45m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$316
This Mytrip deal was found by Cheapflights users on 2/1. 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.
Fri 4/1011:10 am
GCM
- ORD
1 stop8h 15m
Multiple Airlines
Sat 4/115:05 am
ORD
- GCM
1 stop7h 15m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$361
This Expedia deal was found by Cheapflights users on 2/1. 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.
Fri 4/1011:10 am
GCM
- ORD
2 stops24h 27m
Air Canada
Sat 4/116:01 pm
ORD
- GCM
2 stops40h 14m
Air Canada
Deal found 2/1![Air Canada logo]()
$428
This American Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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.
Thu 2/193:35 pm
GCM
- ORD
Nonstop4h 10m
American Airlines
Wed 2/256:10 am
ORD
- GCM
1 stop8h 15m
American Airlines
Deal found 1/31![American Airlines logo]()
$453
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Wed 4/11:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Mon 4/68:10 pm
ORD
- GCM
1 stop16h 20m
United Airlines
Deal found 2/1![United Airlines logo]()
$491
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/191:50 pm
GCM
- MDW
1 stop9h 35m
Southwest
Wed 2/255:00 am
MDW
- GCM
1 stop6h 55m
Southwest
Deal found 1/31![Southwest logo]()
$495
This Delta deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” 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 3/171:12 pm
GCM
- MDW
1 stop9h 19m
Delta
Tue 3/246:00 am
MDW
- GCM
1 stop5h 47m
Delta
Deal found 1/30![Delta logo]()
$496
This Kiwi.com deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” 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 3/1711:30 am
GCM
- ORD
1 stop20h 55m
Multiple Airlines
Tue 3/244:51 pm
ORD
- GCM
1 stop23h 14m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$363
This Southwest deal was found by Cheapflights users on 2/1. 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.
Wed 4/112:20 pm
GCM
- MDW
2 stops11h 35m
Southwest
Mon 4/66:25 pm
MDW
- GCM
2 stops17h 45m
Southwest
Deal found 2/1![Southwest logo]()
$537
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/131:54 pm
GCM
- MDW
1 stop9h 37m
Delta
Wed 2/186:00 am
MDW
- GCM
1 stop5h 29m
Delta
Deal found 2/1![Delta logo]()
$540
This Southwest deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” 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 3/1712:40 pm
GCM
- MDW
1 stop6h 40m
Southwest
Tue 3/246:35 pm
MDW
- GCM
2 stops17h 10m
Southwest
Deal found 1/30![Southwest logo]()
$564
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/11:12 pm
GCM
- MDW
1 stop9h 19m
Delta
Mon 4/66:00 am
MDW
- GCM
1 stop5h 47m
Delta
Deal found 2/1![Delta logo]()
$1,682
Last-minute flights from Grand Cayman to IllinoisDiscover last-minute flight deals from Grand Cayman to Illinois. Data last updated February 2, 2026 and is based on user searches.
Discover last-minute flight deals from Grand Cayman to Illinois. Data last updated February 2, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/133:35 pm
GCM
- ORD
Nonstop4h 10m
American Airlines
Wed 2/189:36 am
ORD
- GCM
Nonstop3h 59m
American Airlines
Deal found 2/2![American Airlines logo]()
$495
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/131:54 pm
GCM
- MDW
1 stop9h 37m
Delta
Wed 2/186:00 am
MDW
- GCM
1 stop5h 29m
Delta
Deal found 2/1![Delta logo]()
$540
This Orbitz deal was found by Cheapflights users on 2/1. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/143:40 pm
GCM
- ORD
1 stop8h 41m
JetBlue
Wed 2/1810:00 am
ORD
- GCM
2 stops27h 05m
JetBlue
Deal found 2/1![JetBlue logo]()
$523
This American Airlines deal was found by Cheapflights users on 2/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/144:00 pm
GCM
- ORD
Nonstop4h 20m
American Airlines
Wed 2/189:36 am
ORD
- GCM
Nonstop3h 59m
American Airlines
Deal found 2/1![American Airlines logo]()
$525
This Orbitz deal was found by Cheapflights users on 2/1. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/1411:10 am
GCM
- ORD
1 stop13h 11m
Multiple Airlines
Wed 2/188:40 pm
ORD
- GCM
1 stop14h 45m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$536
This Mytrip deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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.
Thu 2/192:49 pm
GCM
- ORD
1 stop7h 24m
Spirit Airlines
Wed 2/255:58 pm
ORD
- GCM
2 stops18h 45m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$316
This American Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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.
Thu 2/193:35 pm
GCM
- ORD
Nonstop4h 10m
American Airlines
Wed 2/256:10 am
ORD
- GCM
1 stop8h 15m
American Airlines
Deal found 1/31![American Airlines logo]()
$453
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/191:50 pm
GCM
- MDW
1 stop9h 35m
Southwest
Wed 2/255:00 am
MDW
- GCM
1 stop6h 55m
Southwest
Deal found 1/31![Southwest logo]()
$495
One-way flights from Grand Cayman to IllinoisSearch for one-way flight options from Grand Cayman to Illinois. Find affordable one-way fares based on user searches. Data last updated February 2, 2026.
Search for one-way flight options from Grand Cayman to Illinois. Find affordable one-way fares based on user searches. Data last updated February 2, 2026.
This FlightHub deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” 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 4/301:40 pm
GCM
- ORD
1 stop10h 01m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Thu 2/262:49 pm
GCM
- ORD
1 stop9h 16m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Thu 2/262:49 pm
GCM
- ORD
2 stops34h 51m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 3/12:49 pm
GCM
- ORD
2 stops45h 58m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 2/274:45 pm
GCM
- ORD
1 stop18h 53m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Tue 3/311:30 am
GCM
- ORD
1 stop23h 09m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Sun 3/12:49 pm
GCM
- ORD
2 stops27h 34m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 2/2511:30 am
GCM
- ORD
1 stop23h 09m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/24:45 pm
GCM
- ORD
2 stops25h 07m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/3111:30 am
GCM
- ORD
1 stop22h 20m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$258
This Delta deal was found by Cheapflights users on 2/2. 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.
Sun 4/51:12 pm
GCM
- MDW
1 stop9h 19m
Delta
Deal found 2/2![Delta logo]()
$659
This Southwest deal was found by Cheapflights users on 2/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/512:55 pm
GCM
- MDW
2 stops11h 10m
Southwest
Deal found 2/2![Southwest logo]()
$681
Find flight deals from Grand Cayman to Illinois
Keep the following information in mind while searching for Grand Cayman to Illinois flight deals. Data was last updated February 2, 2026.
Round-trip from | $316 (Mytrip) |
|---|---|
One-way from | $199 (FlightHub) |
Popular in | March |
Cheapest in | February |
Average price | $454 |
Cheapflights Fare Finder
Customize your flight search to find flights from Grand Cayman to Illinois 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 2, 2026.
Use the filters below to find and compare flights from Grand Cayman to Illinois that are best for you.
Fly from
Grand Cayman
Fly to
Illinois
Route
Depart
Return
Price
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Thu 2/19
2:49 pm-9:13 pm
1 stop7h 24m
Chicago O'Hare Intl
Wed 2/25
5:58 pm-1:43 pm
2 stops18h 45m
$316
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Fri 4/10
11:10 am-7:25 pm
1 stop8h 15m
Chicago O'Hare Intl
Sat 4/11
5:05 am-12:20 pm
1 stop7h 15m
$361
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Tue 3/17
11:30 am-8:25 am
1 stop20h 55m
Chicago O'Hare Intl
Tue 3/24
4:51 pm-4:05 pm
1 stop23h 14m
$363
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Fri 4/10
11:10 am-11:37 am
2 stops24h 27m
Chicago O'Hare Intl
Sat 4/11
6:01 pm-10:15 am
2 stops40h 14m
$428
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Thu 2/19
3:35 pm-6:45 pm
Nonstop4h 10m
Chicago O'Hare Intl
Wed 2/25
6:10 am-3:25 pm
1 stop8h 15m
$453
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Wed 4/1
1:50 pm-6:13 pm
Nonstop4h 23m
Chicago O'Hare Intl
Mon 4/6
8:10 pm-12:30 pm
1 stop16h 20m
$491
George TownChicago
GCM - MDW
GCMMDW
George Town Owen Roberts Intl
Thu 2/19
1:50 pm-10:25 pm
1 stop9h 35m
Chicago Midway
Wed 2/25
5:00 am-12:55 pm
1 stop6h 55m
$495
George TownChicago
GCM - MDW
GCMMDW
George Town Owen Roberts Intl
Tue 3/17
1:12 pm-10:31 pm
1 stop9h 19m
Chicago Midway
Tue 3/24
6:00 am-11:47 am
1 stop5h 47m
$496
George TownChicago
GCM - MDW
GCMMDW
George Town Owen Roberts Intl
Wed 4/1
12:20 pm-11:55 pm
2 stops11h 35m
Chicago Midway
Mon 4/6
6:25 pm-12:10 pm
2 stops17h 45m
$537
George TownChicago
GCM - MDW
GCMMDW
George Town Owen Roberts Intl
Fri 2/13
1:54 pm-10:31 pm
1 stop9h 37m
Chicago Midway
Wed 2/18
6:00 am-12:29 pm
1 stop5h 29m
$540
Showing 1-10 of 23 results
Best time to book a flight from Grand Cayman to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Grand Cayman with our price prediction graph.
GCM-ORD
GCM-MDW
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.
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Everything you need to know about your flight from Grand Cayman to Illinois
zzLAW-USIL
GCM-ORD
GCM-MDW
What is the cheapest time of day to fly from LAW to IL?
Find hourly flight availability from Grand Cayman to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 2, 2026.
When flying from Grand Cayman to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated February 2, 2026.
Read reviews from past customers who have flown American Airlines from Grand Cayman to Illinois. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
6.9
Comfort
7.2
Boarding
7.5
Overall
7.2
Crew
8.0
Food
6.4
Reviews
1 / 20
2.0
MediocreSusie,Jan 2026
CLT - TPA
Entertainment
6.9
Comfort
7.2
Boarding
7.5
Overall
7.2
Crew
8.0
Food
6.4
Reviews
1 / 20
2.0
MediocreSusie,Jan 2026
CLT - TPA