HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Cayman Islands

$72+ Cheap flights from Illinois to the Cayman Islands

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.
ORD — GCM
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Illinois to Cayman Islands 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 Illinois to Cayman Islands

Cheapest flights from Illinois to Cayman Islands
Explore the most affordable flight options available from Illinois to Cayman Islands. 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 12/17. 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 12/316:05 pmORD - GCM
1 stop16h 30mMultiple Airlines
Wed 1/711:30 amGCM - ORD
1 stop21h 48mMultiple Airlines
Deal found 12/17$368
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/248:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Wed 12/312:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 12/17$438
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:30 amORD - GCM
1 stop6h 06mDelta
Wed 12/313:42 pmGCM - ORD
1 stop9h 20mDelta
Deal found 12/16$452
This American Airlines deal was found by Cheapflights users on 12/18. 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.
Wed 12/249:24 amORD - GCM
Nonstop4h 11mAmerican Airlines
Wed 12/313:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 12/18$463
This United Airlines deal was found by Cheapflights users on 12/17. 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 12/188:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Thu 12/252:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 12/17$468
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Mon 12/295:10 pmGCM - ORD
1 stop7h 34mUnited Airlines
Deal found 12/16$478
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/255:30 amORD - GCM
1 stop7h 57mDelta
Wed 12/311:52 pmGCM - ORD
1 stop11h 10mDelta
Deal found 12/16$482
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/259:24 amORD - GCM
Nonstop4h 11mAmerican Airlines
Wed 12/313:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 12/16$493
This Southwest deal was found by Cheapflights users on 12/17. 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 12/185:50 amMDW - GCM
1 stop5h 45mSouthwest
Thu 12/251:30 pmGCM - MDW
1 stop8h 10mSouthwest
Deal found 12/17$522
This Delta deal was found by Cheapflights users on 12/17. 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.
Wed 12/246:00 amMDW - GCM
1 stop5h 36mDelta
Wed 12/311:52 pmGCM - MDW
1 stop9h 30mDelta
Deal found 12/17$559
This Delta deal was found by Cheapflights users on 12/17. 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 12/266:00 amMDW - GCM
1 stop7h 27mDelta
Wed 12/313:42 pmGCM - MDW
1 stop7h 40mDelta
Deal found 12/17$651
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/206:35 pmSTL - GCM
2 stops20h 25mUnited Airlines
Sat 12/275:45 pmGCM - STL
1 stop17h 04mUnited Airlines
Deal found 12/16$657

Find flight deals from Illinois to Cayman Islands

Keep the following information in mind while searching for Illinois to Cayman Islands flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$240
(Mytrip)

One-way from

$72
(Priceline)

Popular in

December

Cheapest in

October

Average price

$827

Good round-trip deal

$449 or less

Good one-way deal

$288 or less
Provider with most accurate pricing for Chicago (CHI)-George Town Owen Roberts Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-George Town Owen Roberts Intl flights.
Search Deals
From Illinois to Cayman Islands
Search Deals
One-way flight from Illinois to Cayman Islands
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Illinois to Cayman Islands.
Search Deals
Price to beat on a one-way flight from Illinois to Cayman Islands.
Search Deals

Cheapflights Fare Finder

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

Fly from

Illinois

Fly to

Cayman Islands

Route

Depart

Return

Price

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Mon 1/26

6:00 am-12:40 pm

1 stop5h 40m

George Town Owen Roberts Intl

Tue 2/3

2:05 pm-8:37 pm

1 stop7h 32m

$352

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Wed 1/28

6:00 am-12:40 pm

1 stop5h 40m

George Town Owen Roberts Intl

Tue 2/3

2:05 pm-11:37 pm

1 stop10h 32m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 3/28

3:55 pm-11:10 am

1 stop19h 15m

George Town Owen Roberts Intl

Fri 4/3

12:30 pm-10:03 pm

1 stop9h 33m

$361

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 3/29

4:43 pm-11:10 am

1 stop18h 27m

George Town Owen Roberts Intl

Fri 4/3

12:30 pm-9:55 am

1 stop21h 25m

$361

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 1/15

8:45 pm-12:25 pm

1 stop14h 40m

George Town Owen Roberts Intl

Mon 1/19

1:30 pm-10:05 pm

1 stop9h 35m

$361

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/10

4:38 pm-1:53 pm

3 stops20h 15m

George Town Owen Roberts Intl

Sat 1/17

2:34 pm-9:12 am

2 stops19h 38m

$364

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Mon 2/16

6:25 am-1:45 pm

1 stop6h 20m

George Town Owen Roberts Intl

Mon 2/23

2:50 pm-10:59 pm

1 stop9h 09m

$372

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Sat 1/24

4:05 pm-12:25 pm

1 stop19h 20m

George Town Owen Roberts Intl

Thu 1/29

1:30 pm-3:29 pm

1 stop26h 59m

$373

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Sat 1/24

4:05 pm-12:25 pm

1 stop19h 20m

George Town Owen Roberts Intl

Mon 2/2

1:30 pm-3:29 pm

1 stop26h 59m

$373

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Fri 1/23

9:59 am-12:50 pm

2 stops25h 51m

George Town Owen Roberts Intl

Tue 2/3

2:05 pm-8:37 pm

1 stop7h 32m

$376

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 44 results
1
2
3
...
5

Best time to book a flight from Illinois to Cayman Islands

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

What is the cheapest month to book a flight from Illinois to Cayman Islands?

Currently, December is the cheapest month in which you can book a flight from Illinois to Cayman Islands (average of $339). Flying from Illinois to Cayman Islands in September is currently the most expensive (average of $650). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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

Find hourly flight availability from Illinois to Cayman Islands. 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.

It’s optimal to fly from Illinois to Cayman Islands at noon. By choosing this option you can save up to 41% on the cost of your flight, compared to a flight in the morning.

Related info for your journey

Find useful and relevant information for your journey from Illinois to Cayman Islands. 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 Illinois to Cayman Islands?

    Airlines like Delta, Air Canada, and Spirit Airlines fly from Illinois to Cayman Islands in about 5h 40m. The time it takes to get you to your destination can typically vary by up to 14h 35m. Airlines will cover a distance of 1448 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

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

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

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

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

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

  • What is the cheapest month to book a flight from Illinois to Cayman Islands?

    Currently, December is the cheapest month in which you can book a flight from Illinois to Cayman Islands (average of $339). Flying from Illinois to Cayman Islands in September is currently the most expensive (average of $650). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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 for Illinois to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Luis Munoz Marin Intl flights
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santiago de los Caballeros flights
John F Kennedy Intl to Santo Domingo flights
LaGuardia to Luis Munoz Marin Intl flights
O'Hare Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Punta Cana flights
Dulles Intl to Luis Munoz Marin Intl flights
Newark to Santo Domingo flights
Newark to Punta Cana flights
Philadelphia to Luis Munoz Marin Intl flights
Orlando to Luis Munoz Marin Intl flights
Boston to Luis Munoz Marin Intl flights
Newark to Santiago de los Caballeros flights
Baltimore to Luis Munoz Marin Intl flights
Reagan-National to Luis Munoz Marin Intl flights
Newark to Oranjestad flights
John F Kennedy Intl to Oranjestad flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
Atlanta to Luis Munoz Marin Intl flights
Hartford to Luis Munoz Marin Intl flights
John F Kennedy Intl to Port of Spain flights
LaGuardia to Punta Cana flights
John F Kennedy Intl to Montego Bay flights
Tampa to Luis Munoz Marin Intl flights
LaGuardia to Santo Domingo flights
Boston to Oranjestad flights
Newark to Simpson Bay flights
Boston to Santo Domingo flights
Raleigh to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
John F Kennedy Intl to Simpson Bay flights
Newark to Nassau flights
Detroit to Luis Munoz Marin Intl flights
Dulles Intl to Punta Cana flights
Boston to Punta Cana flights
Minneapolis to Luis Munoz Marin Intl flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Orlando to Punta Cana flights
Hobby to Luis Munoz Marin Intl flights
Newark to Montego Bay flights
Midway to Luis Munoz Marin Intl flights
John F Kennedy Intl to Kingston flights
John F Kennedy Intl to Nassau flights
LaGuardia to Oranjestad flights
Newark to Saint Thomas Island flights
John F Kennedy Intl to Providenciales flights
John F Kennedy Intl to Saint Thomas Island flights
Miami to Santo Domingo flights
Fort Lauderdale to Santo Domingo flights

Top 2 airlines flying from Illinois to Cayman Islands

Discover the top 2 airlines that operate flights from Illinois to Cayman Islands. 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 2,558,603 searches. Data last updated December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$341Average$680FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$452Average$724FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.