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$176+ Cheap flights from Grand Cayman 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 Grand Cayman to Illinois

Cheapest flights from Grand Cayman to Illinois
Explore the most affordable flight options available from Grand Cayman 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 Grand Cayman to Illinois

Keep the following information in mind while searching for Grand Cayman 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
From Grand Cayman to Illinois
Search Deals
One-way flight from Grand Cayman to Illinois
Search Deals
Highest demand for flights based on searches. 35% potential increase in price ($347 potential increase over avg. RT price).
Search Deals
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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Cheapflights Fare Finder

 
Customize your flight search to find flights from Grand Cayman 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 Grand Cayman to Illinois that are best for you.

Fly from

Grand Cayman

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 Grand Cayman to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Grand Cayman 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 Grand Cayman to Illinois

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

Find hourly flight availability from Grand Cayman 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.

When flying from Grand Cayman to Illinois, 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 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.
Read reviews from past customers who have flown American Airlines from Grand Cayman to Illinois. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,055 reviews

Food

6.5

Boarding

7.5

Entertainment

6.9

Crew

8.0

Overall

7.2

Comfort

7.2

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
11,055 reviews
American Airlines
7.2
Good
11,055 reviews

Food

6.5

Boarding

7.5

Entertainment

6.9

Crew

8.0

Overall

7.2

Comfort

7.2

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 Grand Cayman 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 Grand Cayman to Illinois?

    For as low as $721, Air Canada can have you in Illinois from Grand Cayman in 9h 15m. Grand Cayman and Illinois are separated by a distance of 1598 mi. 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 Grand Cayman to Illinois that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Grand Cayman 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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