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Illinois

$161+ Cheap flights from the Cayman Islands to Illinois

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — ORD
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Cayman Islands to Illinois

Cheapest flights from Cayman Islands to Illinois
Explore the most affordable flight options available from Cayman Islands to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Sun 2/152:49 pm
GCM
-
ORD
2 stops18h 05m
Multiple Airlines
Wed 2/184:43 pm
ORD
-
GCM
1 stop20h 00m
Multiple Airlines
Deal found 1/26$368
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Sun 2/152:49 pm
GCM
-
ORD
1 stop7h 24m
Spirit Airlines
Wed 2/184:43 pm
ORD
-
GCM
1 stop20h 00m
Spirit Airlines
Deal found 1/26$371
This FlightHub deal was found by Cheapflights users on 1/27. 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.
Thu 4/3012:30 pm
GCM
-
ORD
1 stop29h 46m
Air Canada
Fri 5/19:15 pm
ORD
-
GCM
1 stop14h 15m
Air Canada
Deal found 1/27$376
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/1411:25 am
GCM
-
ORD
2 stops13h 22m
Multiple Airlines
Wed 2/184:43 pm
ORD
-
GCM
1 stop20h 00m
Multiple Airlines
Deal found 1/27$419
This Mytrip deal was found by Cheapflights users on 1/28. 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.
Sun 5/311:40 pm
GCM
-
ORD
1 stop10h 01m
Multiple Airlines
Sun 6/79:55 am
ORD
-
GCM
1 stop25h 35m
Multiple Airlines
Deal found 1/28$427
This Gotogate deal was found by Cheapflights users on 1/28. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2712:30 pm
GCM
-
ORD
2 stops22h 23m
Multiple Airlines
Thu 4/307:05 am
ORD
-
GCM
1 stop5h 38m
Multiple Airlines
Deal found 1/28$428
This Southwest deal was found by Cheapflights users on 1/27. 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.
Fri 2/131:50 pm
GCM
-
MDW
1 stop8h 10m
Southwest
Wed 2/185:00 am
MDW
-
GCM
1 stop6h 55m
Southwest
Deal found 1/27$439
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/1311:25 am
GCM
-
ORD
2 stops33h 25m
Multiple Airlines
Wed 2/184:43 pm
ORD
-
GCM
1 stop20h 00m
Multiple Airlines
Deal found 1/27$454
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/131:54 pm
GCM
-
MDW
1 stop9h 37m
Delta
Wed 2/186:20 pm
MDW
-
GCM
2 stops17h 09m
Delta
Deal found 1/27$460
This Southwest deal was found by Cheapflights users on 1/27. 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.
Sat 2/141:25 pm
GCM
-
MDW
1 stop11h 00m
Southwest
Wed 2/185:00 am
MDW
-
GCM
1 stop6h 55m
Southwest
Deal found 1/27$469
This Southwest deal was found by Cheapflights users on 1/27. 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.
Thu 4/301:05 pm
GCM
-
MDW
1 stop10h 35m
Southwest
Fri 5/15:35 am
MDW
-
GCM
1 stop6h 35m
Southwest
Deal found 1/27$484
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/141:54 pm
GCM
-
MDW
2 stops20h 00m
Delta
Wed 2/186:00 am
MDW
-
GCM
1 stop5h 29m
Delta
Deal found 1/27$490

Find flight deals from Cayman Islands to Illinois

Keep the following information in mind while searching for Cayman Islands to Illinois flight deals. Data was last updated January 29, 2026.

Round-trip from

$368
(Kiwi.com)

One-way from

$161
(Priceline)

Popular in

March

Cheapest in

December

Good round-trip deal

$276 or less

Good one-way deal

$318 or less
From Cayman Islands to Illinois
Search Deals
One-way flight from Cayman Islands to Illinois
Search Deals
Highest demand for flights based on searches. 33% potential increase in price ($331 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($39 potential savings vs. average RT price).
Search Deals
Price to beat on a round-trip flight from Cayman Islands to Illinois.
Search Deals
Price to beat on a one-way flight from Cayman Islands to Illinois.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cayman Islands to Illinois that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
Use the filters below to find and compare flights from the Cayman Islands to Illinois that are best for you.

Fly from

Cayman Islands

Fly to

Illinois

Route

Depart

Return

Price

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sun 2/15

2:49 pm-7:54 am

2 stops18h 05m

Chicago O'Hare Intl

Wed 2/18

4:43 pm-1:43 pm

1 stop20h 00m

$368

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sun 2/15

2:49 pm-9:13 pm

1 stop7h 24m

Chicago O'Hare Intl

Wed 2/18

4:43 pm-1:43 pm

1 stop20h 00m

$371

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 2/14

11:25 am-11:47 pm

2 stops13h 22m

Chicago O'Hare Intl

Wed 2/18

4:43 pm-1:43 pm

1 stop20h 00m

$419

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 4/27

12:30 pm-9:10 am

1 stop20h 40m

Chicago O'Hare Intl

Thu 4/30

5:15 am-12:43 pm

1 stop7h 28m

$425

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sun 5/31

1:40 pm-11:41 pm

1 stop10h 01m

Chicago O'Hare Intl

Sun 6/7

9:55 am-11:30 am

1 stop25h 35m

$427

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 4/30

12:30 pm-11:28 am

2 stops22h 58m

Chicago O'Hare Intl

Fri 5/1

3:40 pm-11:30 am

2 stops19h 50m

$433

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 2/13

1:50 pm-9:00 pm

1 stop8h 10m

Chicago Midway

Wed 2/18

5:00 am-12:55 pm

1 stop6h 55m

$439

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 2/13

3:35 pm-6:45 pm

Nonstop4h 10m

Chicago O'Hare Intl

Wed 2/18

9:36 am-2:35 pm

Nonstop3h 59m

$455

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 2/13

1:54 pm-10:31 pm

1 stop9h 37m

Chicago Midway

Wed 2/18

6:20 pm-12:29 pm

2 stops17h 09m

$460

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 2/14

1:25 pm-11:25 pm

1 stop11h 00m

Chicago Midway

Wed 2/18

5:00 am-12:55 pm

1 stop6h 55m

$469

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 32 results
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Best time to book a flight from Cayman Islands to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Cayman Islands with our price prediction graph.
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 Illinois

What is the cheapest time of day to fly from KY to IL?

Find hourly flight availability from Cayman Islands to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 29, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Cayman Islands to Illinois as you normally would.

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated January 29, 2026.
Get a feel of what it's like to fly with American Airlines from the Cayman Islands to Illinois by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,205 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,205 reviews
American Airlines
7.2
Good
11,205 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

Related info for your journey

Find useful and relevant information for your journey from Cayman Islands to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Cayman Islands to Illinois?

    A quick flight from Cayman Islands to Illinois can take about 7h 24m. Spirit Airlines provides one of the quickest options available for as low as $371. There are 1613 mi between Cayman Islands and Illinois. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from Cayman Islands to Illinois that include hotel bookings?

    Yes. In addition to deals on Cayman Islands to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Cayman Islands to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Cayman Islands to Illinois.

  • Can I find deals for business class flights from Cayman Islands to Illinois?

    Yes. Cheapflights offers flight deals from Cayman Islands to Illinois by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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