$240+ Cheap flights from the Cayman Islands to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/22. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — CHI
Nov 24 — Dec 11
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 October 25, 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 October 25, 2026.
This Trip.com deal was found by Cheapflights users on 10/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/81:10 pm -
1 stop29h 33m
Tue 12/1510:05 am -
1 stop25h 05m
Deal found 10/24![Air Canada logo]()
$381
This Justfly.com deal was found by Cheapflights users on 10/22. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:10 pm -
1 stop8h 38m
Fri 10/308:40 pm -
1 stop14h 30m
Deal found 10/22![Air Canada logo]()
$462
This Orbitz deal was found by Cheapflights users on 10/22. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3112:10 pm -
1 stop26h 03m
Thu 11/510:15 am -
1 stop24h 55m
Deal found 10/22![Air Canada logo]()
$477
This Priceline deal was found by Cheapflights users on 10/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/61:10 pm -
1 stop7h 48m
Sun 12/139:21 pm -
1 stop13h 49m
Deal found 10/21![Air Canada logo]()
$501
This Southwest deal was found by Cheapflights users on 10/24. 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.
Tue 12/81:30 pm -
1 stop7h 05m
Tue 12/155:20 am -
1 stop6h 15m
Deal found 10/24![Southwest logo]()
$510
This Justfly.com deal was found by Cheapflights users on 10/22. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/11:10 pm -
1 stop25h 10m
Thu 11/58:45 am -
1 stop26h 25m
Deal found 10/22![Air Canada logo]()
$520
This Mytrip deal was found by Cheapflights users on 10/21. 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 12/64:45 pm -
3 stops24h 19m
Sun 12/138:50 pm -
1 stop14h 20m
Deal found 10/21![Multiple Airlines logo]()
$543
This Air Canada deal was found by Cheapflights users on 10/22. 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.
Wed 10/2812:10 pm -
1 stop25h 10m
Sat 10/318:45 am -
1 stop27h 25m
Deal found 10/22![Air Canada logo]()
$545
This Southwest deal was found by Cheapflights users on 10/23. 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 12/261:40 pm -
2 stops10h 25m
Fri 1/15:20 am -
1 stop6h 15m
Deal found 10/23![Southwest logo]()
$648
This Mytrip deal was found by Cheapflights users on 10/21. 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 12/64:45 pm -
3 stops25h 31m
Sun 12/135:02 pm -
2 stops23h 18m
Deal found 10/21![Multiple Airlines logo]()
$692
This Southwest deal was found by Cheapflights users on 10/22. 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.
Sun 11/11:30 pm -
1 stop6h 25m
Thu 11/58:25 pm -
2 stops15h 10m
Deal found 10/22![Southwest logo]()
$762
This Delta deal was found by Cheapflights users on 10/23. 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.
Fri 12/253:51 pm -
1 stop7h 31m
Sat 1/26:00 am -
1 stop6h 12m
Deal found 10/23![Delta logo]()
$764
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 October 25, 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 October 25, 2026.
This Trip.com deal was found by Cheapflights users on 10/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/81:10 pm -
1 stop29h 33m
Tue 12/1510:05 am -
1 stop25h 05m
Deal found 10/24![Air Canada logo]()
$381
This Southwest deal was found by Cheapflights users on 10/24. 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.
Tue 12/81:30 pm -
1 stop7h 05m
Tue 12/155:20 am -
1 stop6h 15m
Deal found 10/24![Southwest logo]()
$510
This Mytrip deal was found by Cheapflights users on 10/21. 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 12/64:45 pm -
3 stops24h 19m
Sun 12/138:50 pm -
1 stop14h 20m
Deal found 10/21![Multiple Airlines logo]()
$543
This United Airlines deal was found by Cheapflights users on 10/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/242:55 pm -
Nonstop4h 18m
Sun 3/78:42 am -
Nonstop4h 03m
Deal found 10/22![United Airlines logo]()
$677
This American Airlines deal was found by Cheapflights users on 10/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/243:11 pm -
Nonstop4h 40m
Sun 3/79:45 pm -
1 stop13h 15m
Deal found 10/22![American Airlines logo]()
$681
This Delta deal was found by Cheapflights users on 10/23. 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.
Fri 12/252:27 pm -
1 stop8h 55m
Thu 12/316:00 am -
1 stop7h 36m
Deal found 10/23![Delta logo]()
$764
This Mytrip deal was found by Cheapflights users on 10/21. 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 12/64:45 pm -
3 stops25h 31m
Sun 12/135:02 pm -
2 stops23h 18m
Deal found 10/21![Multiple Airlines logo]()
$692
This United Airlines deal was found by Cheapflights users on 10/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/252:55 pm -
Nonstop4h 18m
Thu 12/318:42 am -
Nonstop4h 03m
Deal found 10/23![United Airlines logo]()
$713
This Delta deal was found by Cheapflights users on 10/23. 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.
Fri 12/253:51 pm -
1 stop7h 31m
Sat 1/26:00 am -
1 stop6h 12m
Deal found 10/23![Delta logo]()
$764
This Southwest deal was found by Cheapflights users on 10/21. 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 12/61:30 pm -
1 stop6h 25m
Sun 12/136:05 pm -
2 stops17h 30m
Deal found 10/21![Southwest logo]()
$797
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/42:55 pm -
Nonstop4h 18m
Fri 2/56:25 pm -
1 stop17h 50m
Deal found 10/21![United Airlines logo]()
$732
This United Airlines deal was found by Cheapflights users on 10/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/252:55 pm -
Nonstop4h 18m
Sat 1/28:42 am -
Nonstop4h 03m
Deal found 10/23![United Airlines logo]()
$738
This Delta deal was found by Cheapflights users on 10/23. 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 12/273:51 pm -
1 stop7h 31m
Sat 1/26:00 am -
1 stop6h 12m
Deal found 10/23![Delta logo]()
$863
This United Airlines deal was found by Cheapflights users on 10/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/252:55 pm -
Nonstop4h 18m
Fri 1/18:42 am -
Nonstop4h 03m
Deal found 10/23![United Airlines logo]()
$738
This WestJet deal was found by Cheapflights users on 10/23. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/273:35 pm -
2 stops20h 26m
Sat 1/26:30 pm -
2 stops43h 05m
Deal found 10/23![WestJet logo]()
$3,722
Last-minute flights from Cayman Islands to ChicagoDiscover last-minute flight deals from Cayman Islands to Chicago. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Cayman Islands to Chicago. Data last updated October 25, 2026 and is based on user searches.
This Justfly.com deal was found by Cheapflights users on 10/22. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:10 pm -
1 stop8h 38m
Fri 10/308:40 pm -
1 stop14h 30m
Deal found 10/22![Air Canada logo]()
$462
This Air Canada deal was found by Cheapflights users on 10/22. 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.
Wed 10/2812:10 pm -
1 stop25h 10m
Sat 10/318:45 am -
1 stop27h 25m
Deal found 10/22![Air Canada logo]()
$545
This Orbitz deal was found by Cheapflights users on 10/22. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3112:10 pm -
1 stop26h 03m
Thu 11/510:15 am -
1 stop24h 55m
Deal found 10/22![Air Canada logo]()
$477
This Mytrip deal was found by Cheapflights users on 10/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3112:10 pm -
1 stop22h 13m
Wed 11/46:30 am -
2 stops28h 05m
Deal found 10/22![Multiple Airlines logo]()
$578
This Mytrip deal was found by Cheapflights users on 10/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3112:10 pm -
1 stop22h 13m
Thu 11/56:00 am -
2 stops14h 15m
Deal found 10/22![Multiple Airlines logo]()
$593
This Mytrip deal was found by Cheapflights users on 10/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3111:25 am -
3 stops25h 00m
Wed 11/46:42 pm -
2 stops25h 33m
Deal found 10/22![Multiple Airlines logo]()
$820
This Delta deal was found by Cheapflights users on 10/22. 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 10/311:05 pm -
1 stop9h 28m
Wed 11/46:44 pm -
2 stops16h 56m
Deal found 10/22![Delta logo]()
$945
This Delta deal was found by Cheapflights users on 10/22. 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 10/311:05 pm -
1 stop9h 28m
Thu 11/56:04 am -
1 stop5h 36m
Deal found 10/22![Delta logo]()
$1,073
This Justfly.com deal was found by Cheapflights users on 10/22. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/11:10 pm -
1 stop25h 10m
Thu 11/58:45 am -
1 stop26h 25m
Deal found 10/22![Air Canada logo]()
$520
This Mytrip deal was found by Cheapflights users on 10/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/11:10 pm -
1 stop29h 33m
Thu 11/56:00 am -
2 stops14h 15m
Deal found 10/22![Multiple Airlines logo]()
$595
This Southwest deal was found by Cheapflights users on 10/22. 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.
Sun 11/11:30 pm -
1 stop6h 25m
Thu 11/58:25 pm -
2 stops15h 10m
Deal found 10/22![Southwest logo]()
$762
This Booking.com deal was found by Cheapflights users on 10/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/14:45 pm -
3 stops19h 40m
Thu 11/56:08 am -
2 stops14h 07m
Deal found 10/22![Multiple Airlines logo]()
$940
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 October 25, 2026.
Search for one-way flight options from Cayman Islands to Chicago. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Trip.com deal was found by Cheapflights users on 10/21. 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.
Sun 11/221:10 pm -
1 stop25h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Air Canada logo]()
$240
This Trip.com deal was found by Cheapflights users on 10/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/41:10 pm -
1 stop27h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Air Canada logo]()
$242
This SmartFares deal was found by Cheapflights users on 10/22. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/21:10 pm -
1 stop19h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Air Canada logo]()
$252
This Air Canada deal was found by Cheapflights users on 10/21. 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.
Tue 11/171:10 pm -
1 stop21h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Air Canada logo]()
$263
This Southwest deal was found by Cheapflights users on 10/22. 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 12/21:30 pm -
1 stop7h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$275
This Southwest deal was found by Cheapflights users on 10/22. 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.
Thu 12/31:30 pm -
2 stops9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$279
This Mytrip deal was found by Cheapflights users on 10/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/511:25 am -
2 stops20h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/164:45 pm -
2 stops32h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$350
This Mytrip deal was found by Cheapflights users on 10/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/31:10 pm -
3 stops19h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1512:40 pm -
3 stops47h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/211:30 am -
3 stops28h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$372
This Southwest deal was found by Cheapflights users on 10/22. 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.
Sat 12/51:55 pm -
1 stop7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$377
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 October 25, 2026.
Round-trip from | $381 (Trip.com) |
|---|---|
One-way from | $240 (Trip.com) |
Good round-trip deal | $426 or less |
Good one-way deal | $270 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 7,457,451 searches. Data last updated October 25, 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 George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Tue 11/17
1:10 pm-9:23 am
1 stop21h 13m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$263
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Sun 11/22
1:10 pm-1:13 pm
1 stop25h 03m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$263
George TownChicago
GCM George Town Owen Roberts Intl - MDW Chicago Midway
GCMMDW
George Town Owen Roberts Intl
Thu 12/3
1:30 pm-9:20 pm
1 stop8h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$275
George TownChicago
GCM George Town Owen Roberts Intl - MDW Chicago Midway
GCMMDW
George Town Owen Roberts Intl
Wed 12/2
1:30 pm-7:35 pm
1 stop7h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$275
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Sat 12/5
11:25 am-4:04 pm
3 stops29h 39m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$349
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Thu 12/3
1:10 pm-7:15 am
3 stops19h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$355
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Sun 2/14
1:10 pm-7:58 pm
1 stop7h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$361
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Tue 12/8
1:10 pm-5:43 pm
1 stop29h 33m
Chicago O'Hare Intl
Tue 12/15
10:05 am-12:10 pm
1 stop25h 05m
$381
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Mon 3/8
1:10 pm-9:08 am
1 stop20h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$393
George TownChicago
GCM George Town Owen Roberts Intl - MDW Chicago Midway
GCMMDW
George Town Owen Roberts Intl
Sun 11/22
7:00 am-8:14 am
2 stops26h 14m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$396
Showing 1-10 of 33 resultsSorted by cheapest first
Best time to book a flight from Cayman Islands to Chicago
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GCM-ORD
GCM-MDW
Estimated round-trip price
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Cheapflights Insights
Everything you need to know about your flight from the Cayman Islands to Chicago
KY0-CHI
GCM-ORD
GCM-MDW
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Related info for your journey
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Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Cayman Islands and Chicago flights
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Top airline flying from Cayman Islands to Chicago
Discover the top airline that operate flights from Cayman Islands to Chicago. 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 7,457,451 searches. Data last updated October 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$571 | Average$713 | FlexibilityNo cancel fee | On-time71% |