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$176+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — ORD
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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 December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/15. 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 12/252:40 pmGCM - ORD
1 stop10h 50mMultiple Airlines
Thu 1/16:00 amORD - GCM
2 stops28h 35mMultiple Airlines
Deal found 12/15$434
This United Airlines deal was found by Cheapflights users on 12/14. 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 12/182:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Sun 12/219:23 pmORD - GCM
1 stop17h 37mUnited Airlines
Deal found 12/14$438
This American Airlines deal was found by Cheapflights users on 12/15. 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.
Mon 12/223:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Mon 12/296:37 pmORD - GCM
1 stop16h 20mAmerican Airlines
Deal found 12/15$472
This United Airlines deal was found by Cheapflights users on 12/15. 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.
Mon 12/225:45 pmGCM - ORD
1 stop18h 17mUnited Airlines
Mon 12/296:20 pmORD - GCM
1 stop20h 40mUnited Airlines
Deal found 12/15$473
This United Airlines deal was found by Cheapflights users on 12/15. 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 12/252:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Thu 1/18:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Deal found 12/15$508
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/205:56 pmGCM - ORD
1 stop7h 34mSpirit Airlines
Sat 12/277:57 pmORD - GCM
2 stops16h 48mSpirit Airlines
Deal found 12/16$590
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/182:40 pmGCM - ORD
1 stop10h 50mMultiple Airlines
Sun 12/217:57 pmORD - GCM
2 stops38h 38mMultiple Airlines
Deal found 12/14$642
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 12/224:45 pmGCM - ORD
1 stop25h 15mMultiple Airlines
Mon 12/296:00 amORD - GCM
2 stops33h 05mMultiple Airlines
Deal found 12/15$648

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 December 18, 2025.

Round-trip from

$360
(Kiwi.com)

One-way from

$176
(Priceline)

Popular in

March

Cheapest in

January

Average price

$497

Good round-trip deal

$497 or less

Good one-way deal

$331 or less
From Cayman Islands to Illinois
Search Deals
One-way flight from Cayman Islands to Illinois
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Highest demand for flights based on searches. 35% potential increase in price ($347 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($37 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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Price to beat on a round-trip flight from Cayman Islands to Illinois.
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Price to beat on a one-way flight from Cayman Islands to Illinois.
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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 December 18, 2025.
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

Fri 1/30

4:45 pm-8:18 am

1 stop16h 33m

Chicago O'Hare Intl

Sat 2/14

12:06 pm-1:43 pm

1 stop24h 37m

$360

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 1/22

1:30 pm-10:05 pm

1 stop9h 35m

Chicago O'Hare Intl

Mon 1/26

9:15 pm-12:25 pm

1 stop14h 10m

$361

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 1/22

2:50 pm-6:04 pm

Nonstop4h 14m

Chicago O'Hare Intl

Mon 1/26

8:45 am-1:45 pm

Nonstop4h 00m

$438

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 1/30

2:50 pm-6:04 pm

Nonstop4h 14m

Chicago O'Hare Intl

Sat 2/14

7:35 am-4:20 pm

1 stop7h 45m

$508

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 1/30

1:50 pm-10:05 pm

2 stops9h 15m

Chicago Midway

Sat 2/14

6:05 pm-12:55 pm

2 stops17h 50m

$721

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 1/15

2:49 pm-8:57 pm

1 stop7h 08m

$194

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 2/19

2:49 pm-11:24 pm

1 stop9h 35m

$194

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 1/17

2:34 pm-11:46 pm

1 stop10h 12m

$202

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sun 1/11

2:49 pm-11:22 am

1 stop21h 33m

$202

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sun 1/25

2:49 pm-9:03 pm

1 stop7h 14m

$218

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 25 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 December 18, 2025.

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 December 18, 2025.
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
11,054 reviews

Comfort

7.2

Boarding

7.5

Food

6.5

Overall

7.2

Entertainment

6.9

Crew

8.0

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,054 reviews
American Airlines
7.2
Good
11,054 reviews

Comfort

7.2

Boarding

7.5

Food

6.5

Overall

7.2

Entertainment

6.9

Crew

8.0

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

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 9h 15m. Air Canada provides one of the quickest options available for as low as $721. There are 1598 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

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