$228+ Cheap flights from the Cayman Islands to Chicago (CHI)
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 6/22. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — CHI
Jun 27 — Jul 41
Round-trip
1 adult, Economy
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Cheapest flights from Cayman Islands to ChicagoExplore the most affordable flight options available from Cayman Islands to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 28, 2026.
Explore the most affordable flight options available from Cayman Islands to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 28, 2026.
This Southwest deal was found by Cheapflights users on 5/24. 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.
Thu 7/212:50 pm
GCM
- MDW
1 stop8h 35m
Southwest
Mon 7/68:50 pm
MDW
- GCM
2 stops15h 05m
Southwest
Deal found 5/24![Southwest logo]()
$532
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/912:50 pm
GCM
- MDW
1 stop9h 10m
Southwest
Thu 6/186:30 am
MDW
- GCM
1 stop5h 25m
Southwest
Deal found 5/28![Southwest logo]()
$585
This KAYAK deal was found by Cheapflights users on 5/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3010:55 am
GCM
- ORD
1 stop22h 05m
Air Canada
Fri 6/52:00 pm
ORD
- GCM
1 stop20h 00m
Air Canada
Deal found 5/27![Air Canada logo]()
$587
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/111:05 pm
GCM
- MDW
1 stop9h 25m
Southwest
Sat 7/188:10 pm
MDW
- GCM
2 stops15h 45m
Southwest
Deal found 5/26![Southwest logo]()
$661
This American Airlines deal was found by Cheapflights users on 5/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/175:10 pm
GCM
- ORD
1 stop7h 16m
American Airlines
Mon 7/275:00 am
ORD
- GCM
1 stop11h 10m
American Airlines
Deal found 5/24![American Airlines logo]()
$661
This KAYAK deal was found by Cheapflights users on 5/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/112:25 pm
GCM
- ORD
2 stops30h 27m
Air Canada
Fri 6/57:25 am
ORD
- GCM
1 stop26h 35m
Air Canada
Deal found 5/27![Air Canada logo]()
$673
This American Airlines deal was found by Cheapflights users on 5/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/25:10 pm
GCM
- ORD
1 stop15h 58m
American Airlines
Mon 7/66:47 pm
ORD
- GCM
1 stop16h 38m
American Airlines
Deal found 5/24![American Airlines logo]()
$681
This American Airlines deal was found by Cheapflights users on 5/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/114:07 pm
GCM
- ORD
1 stop17h 01m
American Airlines
Sat 7/185:59 pm
ORD
- GCM
1 stop17h 01m
American Airlines
Deal found 5/26![American Airlines logo]()
$701
This United Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/111:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Sat 7/189:29 am
ORD
- GCM
Nonstop4h 01m
United Airlines
Deal found 5/26![United Airlines logo]()
$717
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/3112:50 pm
GCM
- MDW
2 stops10h 15m
Southwest
Tue 6/26:00 am
MDW
- GCM
1 stop6h 10m
Southwest
Deal found 5/26![Southwest logo]()
$776
This Delta deal was found by Cheapflights users on 5/26. 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 7/1112:56 pm
GCM
- MDW
1 stop9h 19m
Delta
Sat 7/186:00 am
MDW
- GCM
1 stop5h 31m
Delta
Deal found 5/26![Delta logo]()
$972
Best flights from Cayman Islands to ChicagoDiscover carefully curated flight deals from Cayman Islands to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 28, 2026.
Discover carefully curated flight deals from Cayman Islands to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 28, 2026.
This Southwest deal was found by Cheapflights users on 5/24. 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.
Thu 7/212:50 pm
GCM
- MDW
1 stop8h 35m
Southwest
Mon 7/68:50 pm
MDW
- GCM
2 stops15h 05m
Southwest
Deal found 5/24![Southwest logo]()
$532
This American Airlines deal was found by Cheapflights users on 5/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/175:10 pm
GCM
- ORD
1 stop7h 16m
American Airlines
Mon 7/275:00 am
ORD
- GCM
1 stop11h 10m
American Airlines
Deal found 5/24![American Airlines logo]()
$661
This United Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/111:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Sat 7/189:29 am
ORD
- GCM
Nonstop4h 01m
United Airlines
Deal found 5/26![United Airlines logo]()
$717
This Delta deal was found by Cheapflights users on 5/26. 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 7/1112:56 pm
GCM
- MDW
1 stop9h 19m
Delta
Sat 7/186:00 am
MDW
- GCM
1 stop5h 31m
Delta
Deal found 5/26![Delta logo]()
$972
This Mytrip deal was found by Cheapflights users on 5/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/174:45 pm
GCM
- ORD
3 stops16h 15m
Multiple Airlines
Mon 7/279:50 am
ORD
- GCM
2 stops48h 35m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$1,014
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/912:50 pm
GCM
- MDW
1 stop9h 10m
Southwest
Thu 6/186:30 am
MDW
- GCM
1 stop5h 25m
Southwest
Deal found 5/28![Southwest logo]()
$585
This American Airlines deal was found by Cheapflights users on 5/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/114:07 pm
GCM
- ORD
1 stop17h 01m
American Airlines
Sat 7/185:59 pm
ORD
- GCM
1 stop17h 01m
American Airlines
Deal found 5/26![American Airlines logo]()
$701
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/111:05 pm
GCM
- MDW
1 stop9h 25m
Southwest
Sat 7/188:10 pm
MDW
- GCM
2 stops15h 45m
Southwest
Deal found 5/26![Southwest logo]()
$661
This United Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/91:35 pm
GCM
- ORD
1 stop18h 22m
United Airlines
Thu 6/185:30 am
ORD
- GCM
1 stop7h 00m
United Airlines
Deal found 5/28![United Airlines logo]()
$852
This American Airlines deal was found by Cheapflights users on 5/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/212:02 pm
GCM
- ORD
2 stops11h 59m
American Airlines
Mon 7/65:00 am
ORD
- GCM
2 stops11h 10m
American Airlines
Deal found 5/24![American Airlines logo]()
$816
This American Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/912:33 pm
GCM
- ORD
2 stops10h 57m
American Airlines
Thu 6/188:00 am
ORD
- GCM
2 stops8h 11m
American Airlines
Deal found 5/28![American Airlines logo]()
$866
This Mytrip deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/91:45 pm
GCM
- ORD
3 stops22h 26m
Multiple Airlines
Thu 6/188:40 pm
ORD
- GCM
2 stops24h 15m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$1,090
This Mytrip deal was found by Cheapflights users on 5/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/24:45 pm
GCM
- ORD
3 stops29h 20m
Multiple Airlines
Mon 7/63:45 pm
ORD
- GCM
2 stops42h 40m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$1,200
Last-minute flights from Cayman Islands to ChicagoDiscover last-minute flight deals from Cayman Islands to Chicago. Data last updated May 28, 2026 and is based on user searches.
Discover last-minute flight deals from Cayman Islands to Chicago. Data last updated May 28, 2026 and is based on user searches.
This KAYAK deal was found by Cheapflights users on 5/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3010:55 am
GCM
- ORD
1 stop22h 05m
Air Canada
Fri 6/52:00 pm
ORD
- GCM
1 stop20h 00m
Air Canada
Deal found 5/27![Air Canada logo]()
$587
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/3112:50 pm
GCM
- MDW
2 stops10h 15m
Southwest
Tue 6/26:00 am
MDW
- GCM
1 stop6h 10m
Southwest
Deal found 5/26![Southwest logo]()
$776
This Gotogate deal was found by Cheapflights users on 5/26. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/316:25 pm
GCM
- ORD
2 stops38h 35m
Multiple Airlines
Fri 6/58:20 pm
ORD
- GCM
1 stop13h 40m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$900
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/3112:50 pm
GCM
- ORD
1 stop9h 05m
Southwest
Tue 6/25:55 am
ORD
- GCM
1 stop6h 15m
Southwest
Deal found 5/26![Southwest logo]()
$902
This KAYAK deal was found by Cheapflights users on 5/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/112:25 pm
GCM
- ORD
2 stops30h 27m
Air Canada
Fri 6/57:25 am
ORD
- GCM
1 stop26h 35m
Air Canada
Deal found 5/27![Air Canada logo]()
$673
This KAYAK deal was found by Cheapflights users on 5/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/112:01 pm
GCM
- ORD
2 stops12h 04m
American Airlines
Fri 6/56:00 am
ORD
- GCM
2 stops10h 11m
American Airlines
Deal found 5/27![American Airlines logo]()
$1,028
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/912:50 pm
GCM
- MDW
1 stop9h 10m
Southwest
Thu 6/186:30 am
MDW
- GCM
1 stop5h 25m
Southwest
Deal found 5/28![Southwest logo]()
$585
This United Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/91:35 pm
GCM
- ORD
1 stop18h 22m
United Airlines
Thu 6/185:30 am
ORD
- GCM
1 stop7h 00m
United Airlines
Deal found 5/28![United Airlines logo]()
$852
This American Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/912:33 pm
GCM
- ORD
2 stops10h 57m
American Airlines
Thu 6/188:00 am
ORD
- GCM
2 stops8h 11m
American Airlines
Deal found 5/28![American Airlines logo]()
$866
One-way flights from Cayman Islands to ChicagoSearch for one-way flight options from Cayman Islands to Chicago. Find affordable one-way fares based on user searches. Data last updated May 28, 2026.
Search for one-way flight options from Cayman Islands to Chicago. Find affordable one-way fares based on user searches. Data last updated May 28, 2026.
This Travelocity deal was found by Cheapflights users on 5/26. 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.
Mon 6/2212:25 pm
GCM
- ORD
1 stop24h 57m
Air Canada
Deal found 5/26![Air Canada logo]()
$228
This Air Canada deal was found by Cheapflights users on 5/25. 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.
Mon 6/1512:25 pm
GCM
- ORD
1 stop25h 00m
Air Canada
Deal found 5/25![Air Canada logo]()
$241
This Orbitz deal was found by Cheapflights users on 5/24. 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.
Mon 7/2012:25 pm
GCM
- ORD
1 stop26h 30m
Air Canada
Deal found 5/24![Air Canada logo]()
$254
This Expedia deal was found by Cheapflights users on 5/24. 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 8/2012:25 pm
GCM
- ORD
2 stops26h 30m
Air Canada
Deal found 5/24![Air Canada logo]()
$258
This Air Canada deal was found by Cheapflights users on 5/24. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1712:25 pm
GCM
- ORD
1 stop28h 32m
Air Canada
Deal found 5/24![Air Canada logo]()
$259
This Expedia deal was found by Cheapflights users on 5/26. 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.
Sat 8/2210:40 am
GCM
- ORD
1 stop22h 20m
Air Canada
Deal found 5/26![Air Canada logo]()
$273
This Expedia deal was found by Cheapflights users on 5/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/231:10 pm
GCM
- ORD
1 stop26h 46m
Air Canada
Deal found 5/27![Air Canada logo]()
$289
This Air Canada deal was found by Cheapflights users on 5/25. 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.
Sat 7/2510:55 am
GCM
- ORD
1 stop22h 05m
Air Canada
Deal found 5/25![Air Canada logo]()
$292
This Orbitz deal was found by Cheapflights users on 5/23. 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.
Thu 11/191:10 pm
GCM
- ORD
1 stop29h 18m
Air Canada
Deal found 5/23![Air Canada logo]()
$312
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2512:56 pm
GCM
- MDW
1 stop9h 19m
Delta
Deal found 5/28![Delta logo]()
$524
This Delta deal was found by Cheapflights users on 5/25. 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 8/71:04 pm
GCM
- MDW
1 stop9h 32m
Delta
Deal found 5/25![Delta logo]()
$546
This WestJet deal was found by Cheapflights users on 5/24. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/251:45 pm
GCM
- MDW
2 stops28h 40m
WestJet
Deal found 5/24![WestJet logo]()
$1,474
Find flight deals from Cayman Islands to Chicago
Keep the following information in mind while searching for Cayman Islands to Chicago flight deals. Data was last updated May 28, 2026.
Round-trip from | $532 (Southwest) |
|---|---|
One-way from | $228 (Travelocity) |
Popular in | April |
Cheapest in | November |
Good round-trip deal | $384 or less |
Good one-way deal | $402 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Cayman Islands to Chicago 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 May 28, 2026.
Use the filters below to find and compare flights from the Cayman Islands to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
George TownChicago
GCM - MDW
GCMMDW
George Town Owen Roberts Intl
Thu 7/2
12:50 pm-9:25 pm
1 stop8h 35m
Chicago Midway
Mon 7/6
8:50 pm-11:55 am
2 stops15h 05m
$532
George TownChicago
GCM - MDW
GCMMDW
George Town Owen Roberts Intl
Tue 6/9
12:50 pm-10:00 pm
1 stop9h 10m
Chicago Midway
Thu 6/18
6:30 am-11:55 am
1 stop5h 25m
$585
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Fri 7/17
5:10 pm-12:26 am
1 stop7h 16m
Chicago O'Hare Intl
Mon 7/27
5:00 am-4:10 pm
1 stop11h 10m
$661
George TownChicago
GCM - MDW
GCMMDW
George Town Owen Roberts Intl
Sat 7/11
1:05 pm-10:30 pm
1 stop9h 25m
Chicago Midway
Sat 7/18
8:10 pm-11:55 am
2 stops15h 45m
$661
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Sat 7/11
4:07 pm-9:08 am
1 stop17h 01m
Chicago O'Hare Intl
Sat 7/18
5:59 pm-11:00 am
1 stop17h 01m
$701
Quickest round-trip
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Sat 7/11
1:50 pm-6:13 pm
Nonstop4h 23m
Chicago O'Hare Intl
Sat 7/18
9:29 am-1:30 pm
Nonstop4h 01m
$717
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Thu 7/2
12:02 pm-12:01 am
2 stops11h 59m
Chicago O'Hare Intl
Mon 7/6
5:00 am-4:10 pm
2 stops11h 10m
$816
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Tue 6/9
1:35 pm-7:57 am
1 stop18h 22m
Chicago O'Hare Intl
Thu 6/18
5:30 am-12:30 pm
1 stop7h 00m
$852
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Tue 6/9
12:33 pm-11:30 pm
2 stops10h 57m
Chicago O'Hare Intl
Thu 6/18
8:00 am-4:11 pm
2 stops8h 11m
$866
George TownChicago
GCM - MDW
GCMMDW
George Town Owen Roberts Intl
Sat 7/11
12:56 pm-10:15 pm
1 stop9h 19m
Chicago Midway
Sat 7/18
6:00 am-11:31 am
1 stop5h 31m
$972
Showing 1-10 of 27 resultsSorted by cheapest first
Best time to book a flight from Cayman Islands to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Cayman Islands 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.
Cheapflights Insights
Everything you need to know about your flight from the Cayman Islands to Chicago
KY0-CHI
GCM-ORD
GCM-MDW
What is the cheapest time of day to fly from KY to CHI?
Find hourly flight availability from Cayman Islands to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 28, 2026.
When flying from Cayman Islands to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Related info for your journey
Find useful and relevant information for your journey from Cayman Islands to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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