$218+ 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — CHI
Sep 26 — Oct 31
Round-trip
1 adult, Economy
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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
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Best
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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 August 27, 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 August 27, 2026.
This Air Canada deal was found by Cheapflights users on 8/25. 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.
Thu 12/31:10 pm -
1 stop7h 48m
Sun 12/68:50 pm -
1 stop14h 20m
Deal found 8/25![Air Canada logo]()
$365
This Travelocity deal was found by Cheapflights users on 8/26. 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 10/2411:25 am -
1 stop21h 58m
Sat 10/314:30 pm -
1 stop19h 40m
Deal found 8/26![Air Canada logo]()
$387
This Air Canada deal was found by Cheapflights users on 8/23. 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.
Thu 10/812:25 pm -
2 stops19h 19m
Sun 10/118:40 pm -
1 stop14h 45m
Deal found 8/23![Air Canada logo]()
$441
This Southwest deal was found by Cheapflights users on 8/25. 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 12/51:55 pm -
2 stops16h 45m
Sun 12/133:40 pm -
2 stops19h 55m
Deal found 8/25![Southwest logo]()
$603
This United Airlines deal was found by Cheapflights users on 8/22. 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.
Fri 12/252:55 pm -
Nonstop4h 18m
Wed 12/309:47 pm -
1 stop14h 28m
Deal found 8/22![United Airlines logo]()
$617
This United Airlines deal was found by Cheapflights users on 8/24. 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 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 1/18:30 pm -
1 stop15h 45m
Deal found 8/24![United Airlines logo]()
$642
This Delta deal was found by Cheapflights users on 8/23. 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 10/812:55 pm -
1 stop9h 38m
Sun 10/116:04 am -
1 stop5h 36m
Deal found 8/23![Delta logo]()
$1,332
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 August 27, 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 August 27, 2026.
This Air Canada deal was found by Cheapflights users on 8/25. 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.
Thu 12/31:10 pm -
1 stop7h 48m
Sun 12/68:50 pm -
1 stop14h 20m
Deal found 8/25![Air Canada logo]()
$365
This Southwest deal was found by Cheapflights users on 8/25. 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 12/51:55 pm -
1 stop7h 30m
Sun 12/133:40 pm -
2 stops19h 55m
Deal found 8/25![Southwest logo]()
$603
This United Airlines deal was found by Cheapflights users on 8/22. 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.
Fri 12/252:55 pm -
Nonstop4h 18m
Wed 12/309:47 pm -
1 stop14h 28m
Deal found 8/22![United Airlines logo]()
$617
This American Airlines deal was found by Cheapflights users on 8/22. 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.
Fri 12/255:45 pm -
Nonstop4h 40m
Wed 12/3011:38 am -
Nonstop4h 07m
Deal found 8/22![American Airlines logo]()
$647
This Travelocity deal was found by Cheapflights users on 8/26. 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 10/2411:25 am -
1 stop21h 58m
Sat 10/314:30 pm -
1 stop19h 40m
Deal found 8/26![Air Canada logo]()
$387
This Air Canada deal was found by Cheapflights users on 8/23. 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.
Thu 10/812:25 pm -
2 stops19h 19m
Sun 10/118:40 pm -
1 stop14h 45m
Deal found 8/23![Air Canada logo]()
$441
This United Airlines deal was found by Cheapflights users on 8/24. 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 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 1/18:30 pm -
1 stop15h 45m
Deal found 8/24![United Airlines logo]()
$642
This Delta deal was found by Cheapflights users on 8/23. 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 10/812:55 pm -
1 stop9h 38m
Sun 10/116:04 am -
1 stop5h 36m
Deal found 8/23![Delta logo]()
$1,332
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 August 27, 2026.
Search for one-way flight options from Cayman Islands to Chicago. Find affordable one-way fares based on user searches. Data last updated August 27, 2026.
This Trip.com deal was found by Cheapflights users on 8/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/241:10 pm -
1 stop27h 28m
Deal found 8/25![Air Canada logo]()
$218
This Orbitz deal was found by Cheapflights users on 8/24. 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.
Thu 10/2212:25 pm -
1 stop20h 35m
Deal found 8/24![Air Canada logo]()
$232
This Expedia deal was found by Cheapflights users on 8/26. 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.
Sun 10/2512:10 pm -
2 stops46h 57m
Deal found 8/26![Air Canada logo]()
$236
This Trip.com deal was found by Cheapflights users on 8/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1412:25 pm -
1 stop20h 35m
Deal found 8/23![Air Canada logo]()
$242
This Orbitz deal was found by Cheapflights users on 8/24. 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.
Thu 9/2412:25 pm -
1 stop26h 30m
Deal found 8/24![Air Canada logo]()
$252
This Orbitz deal was found by Cheapflights users on 8/22. 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.
Mon 9/2112:25 pm -
2 stops26h 27m
Deal found 8/22![Air Canada logo]()
$269
This Southwest deal was found by Cheapflights users on 8/22. 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 11/111:30 pm -
2 stops10h 10m
Deal found 8/22![Southwest logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 10/2811:30 am -
2 stops32h 29m
Deal found 8/26![Multiple Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:00 am -
2 stops29h 51m
Deal found 8/24![Multiple Airlines logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:00 am -
2 stops16h 44m
Deal found 8/24![Multiple Airlines logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:50 am -
2 stops13h 57m
Deal found 8/24![Multiple Airlines logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 8/23. 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.
Mon 9/144:45 pm -
2 stops25h 01m
Deal found 8/23![Multiple Airlines logo]()
$394
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 August 27, 2026.
Round-trip from | $365 (Air Canada) |
|---|---|
One-way from | $218 (Trip.com) |
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 August 27, 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
Thu 12/3
1:10 pm-7:58 pm
1 stop7h 48m
Chicago O'Hare Intl
Sun 12/6
8:50 pm-12:10 pm
1 stop14h 20m
$365
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Sat 10/24
11:25 am-9:23 am
1 stop21h 58m
Chicago O'Hare Intl
Sat 10/31
4:30 pm-12:10 pm
1 stop19h 40m
$387
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Thu 10/8
12:25 pm-7:44 am
2 stops19h 19m
Chicago O'Hare Intl
Sun 10/11
8:40 pm-11:25 am
1 stop14h 45m
$441
George TownChicago
GCM George Town Owen Roberts Intl - MDW Chicago Midway
GCMMDW
George Town Owen Roberts Intl
Sat 12/5
1:55 pm-8:25 pm
1 stop7h 30m
Chicago Midway
Sun 12/13
3:40 pm-12:35 pm
2 stops19h 55m
$603
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Fri 12/25
2:55 pm-6:13 pm
Nonstop4h 18m
Chicago O'Hare Intl
Wed 12/30
9:47 pm-1:15 pm
1 stop14h 28m
$617
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Fri 12/25
2:55 pm-6:13 pm
Nonstop4h 18m
Chicago O'Hare Intl
Fri 1/1
8:30 pm-1:15 pm
1 stop15h 45m
$642
Quickest round-trip
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Fri 12/25
5:45 pm-9:25 pm
Nonstop4h 40m
Chicago O'Hare Intl
Wed 12/30
11:38 am-4:45 pm
Nonstop4h 07m
$647
George TownChicago
GCM George Town Owen Roberts Intl - MDW Chicago Midway
GCMMDW
George Town Owen Roberts Intl
Thu 10/8
12:55 pm-10:33 pm
1 stop9h 38m
Chicago Midway
Sun 10/11
6:04 am-11:40 am
1 stop5h 36m
$1,332
Cheapest one-way
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Sat 9/26
10:40 am-1:23 pm
1 stop26h 43m
$242
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Sat 9/19
10:40 am-8:00 am
1 stop21h 20m
$270
Showing 1-10 of 23 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
No data available for this route at this time. Please check back soon.
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
Valparaiso
Hammond
Saint Joseph
Porter
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Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 27, 2026.
Complete your trip
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Cayman Islands and Chicago flights
Browse other Cayman Islands and Chicago flight options. Last updated on August 27, 2026.
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Check out other popular destinations found by fellow travelers in 2026
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 August 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$571 | Average$713 | FlexibilityNo cancel fee | On-time71% |