$227+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — CHI
May 1 — May 81
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Cayman Islands to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Cayman Islands to Chicago
Cheapest
Best
Last-minute
One-way
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 April 1, 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 April 1, 2026.
This Expedia deal was found by Cheapflights users on 4/1. 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.
Mon 6/1512:25 pm
GCM
- ORD
1 stop25h 00m
Air Canada
Sun 6/218:40 pm
ORD
- GCM
1 stop14h 45m
Air Canada
Deal found 4/1![Air Canada logo]()
$345
This Air Canada deal was found by Cheapflights users on 3/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1112:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Fri 6/268:40 pm
ORD
- GCM
1 stop13h 05m
Air Canada
Deal found 3/31![Air Canada logo]()
$373
This flygcity.se deal was found by Cheapflights users on 3/27. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1711:10 am
GCM
- ORD
2 stops20h 48m
Air Canada
Sun 4/265:57 pm
ORD
- GCM
1 stop16h 18m
Air Canada
Deal found 3/27![Air Canada logo]()
$383
This Gotogate deal was found by Cheapflights users on 3/31. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:55 am
GCM
- ORD
1 stop25h 10m
Air Canada
Wed 4/292:00 pm
ORD
- GCM
1 stop21h 10m
Air Canada
Deal found 3/31![Air Canada logo]()
$425
This Southwest deal was found by Cheapflights users on 3/30. 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.
Thu 4/301:05 pm
GCM
- MDW
2 stops10h 50m
Southwest
Mon 5/45:35 am
MDW
- GCM
1 stop6h 35m
Southwest
Deal found 3/30![Southwest logo]()
$476
This Southwest deal was found by Cheapflights users on 3/30. 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.
Thu 4/301:05 pm
GCM
- ORD
1 stop8h 50m
Southwest
Mon 5/46:00 am
ORD
- GCM
1 stop6h 10m
Southwest
Deal found 3/30![Southwest logo]()
$502
This Southwest deal was found by Cheapflights users on 3/30. 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.
Fri 5/11:05 pm
GCM
- MDW
1 stop11h 00m
Southwest
Mon 5/45:35 am
MDW
- GCM
1 stop6h 35m
Southwest
Deal found 3/30![Southwest logo]()
$506
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Thu 4/304:45 pm
GCM
- ORD
1 stop7h 14m
Multiple Airlines
Mon 5/48:58 pm
ORD
- GCM
2 stops43h 07m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$506
This Southwest deal was found by Cheapflights users on 3/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/111:05 pm
GCM
- MDW
1 stop11h 10m
Southwest
Mon 5/189:25 pm
MDW
- GCM
2 stops14h 45m
Southwest
Deal found 3/27![Southwest logo]()
$525
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:25 pm
GCM
- MDW
1 stop9h 03m
Delta
Wed 4/296:00 am
MDW
- GCM
1 stop6h 00m
Delta
Deal found 3/31![Delta logo]()
$586
This Southwest deal was found by Cheapflights users on 3/30. 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.
Fri 5/151:05 pm
GCM
- MDW
1 stop11h 10m
Southwest
Mon 5/189:25 pm
MDW
- GCM
2 stops14h 45m
Southwest
Deal found 3/30![Southwest logo]()
$589
This Southwest deal was found by Cheapflights users on 3/30. 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.
Mon 5/181:05 pm
GCM
- MDW
1 stop7h 35m
Southwest
Wed 5/206:00 am
MDW
- GCM
1 stop6h 10m
Southwest
Deal found 3/30![Southwest logo]()
$593
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 April 1, 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 April 1, 2026.
This Air Canada deal was found by Cheapflights users on 4/1. 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 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
2 stops19h 20m
Air Canada
Sun 6/218:40 pm
ORD
- GCM
1 stop14h 45m
Air Canada
Deal found 4/1![Air Canada logo]()
$350
This Southwest deal was found by Cheapflights users on 3/30. 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.
Fri 5/11:05 pm
GCM
- ORD
1 stop8h 50m
Southwest
Mon 5/46:00 am
ORD
- GCM
1 stop6h 10m
Southwest
Deal found 3/30![Southwest logo]()
$502
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:25 pm
GCM
- MDW
1 stop9h 03m
Delta
Wed 4/296:00 am
MDW
- GCM
1 stop6h 00m
Delta
Deal found 3/31![Delta logo]()
$586
This flygcity.se deal was found by Cheapflights users on 3/27. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1711:10 am
GCM
- ORD
1 stop8h 15m
Air Canada
Sun 4/265:57 pm
ORD
- GCM
1 stop16h 18m
Air Canada
Deal found 3/27![Air Canada logo]()
$383
This Southwest deal was found by Cheapflights users on 3/30. 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.
Fri 5/11:05 pm
GCM
- MDW
1 stop11h 00m
Southwest
Mon 5/45:35 am
MDW
- GCM
1 stop6h 35m
Southwest
Deal found 3/30![Southwest logo]()
$506
This FlightHub deal was found by Cheapflights users on 3/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2711:25 am
GCM
- ORD
1 stop25h 40m
Air Canada
Wed 4/297:55 am
ORD
- GCM
1 stop27h 15m
Air Canada
Deal found 3/27![Air Canada logo]()
$515
This Southwest deal was found by Cheapflights users on 3/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/111:05 pm
GCM
- MDW
1 stop11h 10m
Southwest
Mon 5/189:25 pm
MDW
- GCM
2 stops14h 45m
Southwest
Deal found 3/27![Southwest logo]()
$525
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/271:25 pm
GCM
- MDW
1 stop9h 03m
Delta
Wed 4/296:00 am
MDW
- GCM
1 stop6h 00m
Delta
Deal found 3/31![Delta logo]()
$631
This Southwest deal was found by Cheapflights users on 3/30. 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.
Fri 5/151:05 pm
GCM
- MDW
1 stop11h 10m
Southwest
Mon 5/189:25 pm
MDW
- GCM
2 stops14h 45m
Southwest
Deal found 3/30![Southwest logo]()
$589
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/111:05 pm
GCM
- MDW
1 stop11h 10m
Southwest
Wed 5/138:55 pm
MDW
- GCM
2 stops15h 15m
Southwest
Deal found 3/29![Southwest logo]()
$599
This Southwest deal was found by Cheapflights users on 3/31. 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 4/231:05 pm
GCM
- MDW
2 stops10h 50m
Southwest
Wed 4/298:50 pm
MDW
- GCM
2 stops15h 20m
Southwest
Deal found 3/31![Southwest logo]()
$650
Last-minute flights from Cayman Islands to ChicagoDiscover last-minute flight deals from Cayman Islands to Chicago. Data last updated April 1, 2026 and is based on user searches.
Discover last-minute flight deals from Cayman Islands to Chicago. Data last updated April 1, 2026 and is based on user searches.
This flygcity.se deal was found by Cheapflights users on 3/27. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1711:10 am
GCM
- ORD
2 stops20h 48m
Air Canada
Sun 4/265:57 pm
ORD
- GCM
1 stop16h 18m
Air Canada
Deal found 3/27![Air Canada logo]()
$383
This Gotogate deal was found by Cheapflights users on 3/31. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:55 am
GCM
- ORD
1 stop25h 10m
Air Canada
Wed 4/292:00 pm
ORD
- GCM
1 stop21h 10m
Air Canada
Deal found 3/31![Air Canada logo]()
$425
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:25 pm
GCM
- MDW
1 stop9h 03m
Delta
Wed 4/296:00 am
MDW
- GCM
1 stop6h 00m
Delta
Deal found 3/31![Delta logo]()
$586
This Air Canada deal was found by Cheapflights users on 3/29. 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 4/2711:25 am
GCM
- ORD
1 stop27h 50m
Air Canada
Wed 4/297:55 am
ORD
- GCM
1 stop27h 15m
Air Canada
Deal found 3/29![Air Canada logo]()
$515
This Southwest deal was found by Cheapflights users on 3/30. 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.
Thu 4/301:05 pm
GCM
- MDW
2 stops10h 50m
Southwest
Mon 5/49:25 pm
MDW
- GCM
2 stops14h 45m
Southwest
Deal found 3/30![Southwest logo]()
$476
This Southwest deal was found by Cheapflights users on 3/30. 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.
Thu 4/301:05 pm
GCM
- ORD
1 stop8h 50m
Southwest
Mon 5/46:00 am
ORD
- GCM
1 stop6h 10m
Southwest
Deal found 3/30![Southwest logo]()
$502
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Thu 4/304:45 pm
GCM
- ORD
1 stop7h 14m
Multiple Airlines
Mon 5/48:58 pm
ORD
- GCM
2 stops43h 07m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$506
This Southwest deal was found by Cheapflights users on 3/30. 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.
Fri 5/11:05 pm
GCM
- MDW
1 stop11h 00m
Southwest
Mon 5/45:35 am
MDW
- GCM
1 stop6h 35m
Southwest
Deal found 3/30![Southwest logo]()
$506
This Southwest deal was found by Cheapflights users on 3/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/111:05 pm
GCM
- MDW
1 stop11h 10m
Southwest
Mon 5/189:25 pm
MDW
- GCM
2 stops14h 45m
Southwest
Deal found 3/27![Southwest logo]()
$525
This Orbitz deal was found by Cheapflights users on 3/29. 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 5/1112:25 pm
GCM
- ORD
1 stop20h 40m
Multiple Airlines
Wed 5/139:49 am
ORD
- GCM
2 stops26h 56m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$534
This Southwest deal was found by Cheapflights users on 3/30. 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.
Thu 5/141:05 pm
GCM
- ORD
1 stop8h 50m
Southwest
Thu 5/216:00 am
ORD
- GCM
1 stop6h 10m
Southwest
Deal found 3/30![Southwest logo]()
$544
This Southwest deal was found by Cheapflights users on 3/30. 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.
Fri 5/151:05 pm
GCM
- MDW
1 stop11h 10m
Southwest
Mon 5/189:25 pm
MDW
- GCM
2 stops14h 45m
Southwest
Deal found 3/30![Southwest logo]()
$589
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 April 1, 2026.
Search for one-way flight options from Cayman Islands to Chicago. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
This Air Canada deal was found by Cheapflights users on 3/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/112:25 pm
GCM
- ORD
1 stop22h 56m
Air Canada
Deal found 3/30![Air Canada logo]()
$227
This Orbitz deal was found by Cheapflights users on 3/29. 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 6/2912:25 pm
GCM
- ORD
1 stop24h 57m
Air Canada
Deal found 3/29![Air Canada logo]()
$237
This Trip.com deal was found by Cheapflights users on 4/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:45 pm
GCM
- ORD
1 stop7h 14m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$246
This Air Canada deal was found by Cheapflights users on 3/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2812:25 pm
GCM
- ORD
1 stop26h 30m
Air Canada
Deal found 3/31![Air Canada logo]()
$247
This Air Canada deal was found by Cheapflights users on 3/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/212:25 pm
GCM
- ORD
1 stop28h 32m
Air Canada
Deal found 3/31![Air Canada logo]()
$255
This Air Canada deal was found by Cheapflights users on 3/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2411:10 am
GCM
- ORD
1 stop28h 05m
Air Canada
Deal found 3/28![Air Canada logo]()
$257
This Air Canada deal was found by Cheapflights users on 3/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2612:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 3/30![Air Canada logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Wed 4/2911:30 am
GCM
- ORD
1 stop25h 35m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$266
This Southwest deal was found by Cheapflights users on 3/31. 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.
Tue 6/21:05 pm
GCM
- MDW
1 stop8h 20m
Southwest
Deal found 3/31![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 3/29. 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 6/201:05 pm
GCM
- MDW
1 stop9h 20m
Southwest
Deal found 3/29![Southwest logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Mon 6/294:45 pm
GCM
- MDW
2 stops29h 26m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$398
This Delta deal was found by Cheapflights users on 4/1. 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.
Mon 6/2912:59 pm
GCM
- MDW
1 stop9h 18m
Delta
Deal found 4/1![Delta logo]()
$454
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 April 1, 2026.
Round-trip from | $345 (Expedia) |
|---|---|
One-way from | $227 (Air Canada) |
Popular in | April |
Cheapest in | November |
Average price | $965 |
Good round-trip deal | $513 or less |
Good one-way deal | $389 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 April 1, 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 - ORD
GCMORD
George Town Owen Roberts Intl
Mon 6/15
12:25 pm-7:45 am
2 stops19h 20m
Chicago O'Hare Intl
Sun 6/21
8:40 pm-11:25 am
1 stop14h 45m
$350
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Fri 4/17
11:10 am-7:25 pm
1 stop8h 15m
Chicago O'Hare Intl
Sun 4/26
5:57 pm-10:15 am
1 stop16h 18m
$383
Quickest round-trip
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Fri 5/1
1:05 pm-9:55 pm
1 stop8h 50m
Chicago O'Hare Intl
Mon 5/4
6:00 am-12:10 pm
1 stop6h 10m
$502
George TownChicago
GCM - MDW
GCMMDW
George Town Owen Roberts Intl
Fri 5/1
1:05 pm-12:05 am
1 stop11h 00m
Chicago Midway
Mon 5/4
5:35 am-12:10 pm
1 stop6h 35m
$506
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Mon 4/27
11:25 am-1:05 pm
1 stop25h 40m
Chicago O'Hare Intl
Wed 4/29
7:55 am-11:10 am
1 stop27h 15m
$515
George TownChicago
GCM - MDW
GCMMDW
George Town Owen Roberts Intl
Mon 5/11
1:05 pm-12:15 am
1 stop11h 10m
Chicago Midway
Mon 5/18
9:25 pm-12:10 pm
2 stops14h 45m
$525
George TownChicago
GCM - MDW
GCMMDW
George Town Owen Roberts Intl
Thu 4/23
1:25 pm-10:28 pm
1 stop9h 03m
Chicago Midway
Wed 4/29
6:00 am-12:00 pm
1 stop6h 00m
$586
George TownChicago
GCM - MDW
GCMMDW
George Town Owen Roberts Intl
Fri 5/15
1:05 pm-12:15 am
1 stop11h 10m
Chicago Midway
Mon 5/18
9:25 pm-12:10 pm
2 stops14h 45m
$589
George TownChicago
GCM - MDW
GCMMDW
George Town Owen Roberts Intl
Mon 5/11
1:05 pm-12:15 am
1 stop11h 10m
Chicago Midway
Wed 5/13
8:55 pm-12:10 pm
2 stops15h 15m
$599
George TownChicago
GCM - MDW
GCMMDW
George Town Owen Roberts Intl
Mon 4/27
1:25 pm-10:28 pm
1 stop9h 03m
Chicago Midway
Wed 4/29
6:00 am-12:00 pm
1 stop6h 00m
$631
Showing 1-10 of 26 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 April 1, 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.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated April 1, 2026.
Get a feel of what it's like to fly with American Airlines from the Cayman Islands to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.4
Overall
7.1
Crew
7.9
Boarding
7.5
Comfort
7.2
Entertainment
6.9
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Food
6.4
Overall
7.1
Crew
7.9
Boarding
7.5
Comfort
7.2
Entertainment
6.9
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights