HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Illinois

$264+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — ORD
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Cayman Islands to Illinois 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 Illinois

Keep the following information in mind while searching for Cayman Islands to Illinois flight deals. Data was last updated July 30, 2025.

Round-trip from

$447
(Air Canada)

One-way from

$274
(Delta)

Good round-trip deal

$660 or less

Good one-way deal

$380 or less
From Cayman Islands to Illinois
Search Deals
One-way flight from Cayman Islands to Illinois
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

Find 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 July 30, 2025.

This Southwest deal was found by Cheapflights users on 7/30. 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 11/141:30 pmGCM - ORD
1 stop9h 20mSouthwest
Sun 11/166:05 amORD - GCM
1 stop5h 30mSouthwest
Deal found 7/30$410
This Air Canada deal was found by Cheapflights users on 7/29. 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.
Thu 10/1612:50 pmGCM - ORD
2 stops45h 01mAir Canada
Sat 10/186:00 pmORD - GCM
2 stops41h 55mAir Canada
Deal found 7/29$447
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1212:52 pmGCM - MDW
1 stop8h 44mDelta
Fri 9/196:00 amMDW - GCM
1 stop5h 36mDelta
Deal found 7/29$468
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1212:52 pmGCM - ORD
1 stop11h 02mDelta
Fri 9/195:30 amORD - GCM
1 stop6h 06mDelta
Deal found 7/29$468
This American Airlines deal was found by Cheapflights users on 7/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1212:25 pmGCM - ORD
2 stops11h 23mAmerican Airlines
Fri 9/198:30 pmORD - GCM
2 stops14h 40mAmerican Airlines
Deal found 7/29$481
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/184:45 pmGCM - ORD
1 stop16h 37mMultiple Airlines
Thu 8/2110:27 amORD - GCM
1 stop10h 53mMultiple Airlines
Deal found 7/29$482
This Southwest deal was found by Cheapflights users on 7/30. 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 11/141:30 pmGCM - MDW
2 stops11h 00mSouthwest
Sun 11/166:05 pmMDW - GCM
2 stops17h 30mSouthwest
Deal found 7/30$500
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 7/3112:40 pmGCM - MDW
1 stop9h 44mMultiple Airlines
Thu 8/72:55 pmMDW - GCM
2 stops25h 05mMultiple Airlines
Deal found 7/30$1,052
This Mytrip deal was found by Cheapflights users on 7/28. 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.
Tue 8/121:45 pmGCM - MDW
2 stops23h 18mWestJet
Fri 8/151:43 pmMDW - GCM
2 stops23h 02mWestJet
Deal found 7/28$1,433

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 July 30, 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 11/14

1:30 pm-9:50 pm

1 stop9h 20m

Chicago O'Hare Intl

Sun 11/16

6:05 am-12:35 pm

1 stop5h 30m

$410

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 10/16

12:50 pm-9:51 am

2 stops45h 01m

Chicago O'Hare Intl

Sat 10/18

6:00 pm-11:55 am

2 stops41h 55m

$447

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 9/12

12:52 pm-9:36 pm

1 stop8h 44m

Chicago Midway

Fri 9/19

6:00 am-11:36 am

1 stop5h 36m

$468

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 9/12

12:52 pm-11:54 pm

1 stop11h 02m

Chicago O'Hare Intl

Fri 9/19

5:30 am-11:36 am

1 stop6h 06m

$468

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 9/12

12:25 pm-11:48 pm

2 stops11h 23m

Chicago O'Hare Intl

Fri 9/19

8:30 pm-11:10 am

2 stops14h 40m

$481

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 8/18

4:45 pm-9:22 am

1 stop16h 37m

Chicago O'Hare Intl

Thu 8/21

10:27 am-9:20 pm

1 stop10h 53m

$482

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 11/14

1:30 pm-11:30 pm

2 stops11h 00m

Chicago Midway

Sun 11/16

6:05 pm-12:35 pm

2 stops17h 30m

$500

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Tue 8/12

1:45 pm-1:03 pm

2 stops23h 18m

Chicago Midway

Fri 8/15

1:43 pm-12:45 pm

2 stops23h 02m

$1,433

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 1/14

1:50 pm-9:50 pm

1 stop9h 00m

$264

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 8/28

12:50 pm-10:37 pm

1 stop9h 47m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 18 results
1
2

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 July 30, 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 July 30, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and 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.
Delta
8.0
Very good
7,980 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
United Airlines
7.4
Good
8,896 reviews
Delta
8.0
Very good
7,980 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
WestJet
7.2
Good
2,975 reviews
Delta
8.0
Very good
7,980 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Air Canada
7.1
Good
9,837 reviews
Delta
8.0
Very good
7,980 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.

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.

  • What are the cheapest airlines to fly from Cayman Islands to Illinois one-way?

    One-way options have recently been found by users for as low as $274 on Delta. Other airlines that offer cheap prices include Air Canada from $277 and American Airlines from $278 one-way.

  • 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.

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

    Currently, August is the cheapest month in which you can book a flight from Cayman Islands to Illinois (average of $245). Flying from Cayman Islands to Illinois in March is currently the most expensive (average of $321). 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 Cayman Islands to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
Luis Munoz Marin Intl to Orlando flights
Luis Munoz Marin Intl to John F Kennedy Intl flights
Luis Munoz Marin Intl to Newark flights
Santo Domingo to John F Kennedy Intl flights
Santo Domingo to Newark flights
Luis Munoz Marin Intl to LaGuardia flights
Santiago de los Caballeros to John F Kennedy Intl flights
Luis Munoz Marin Intl to Miami flights
Luis Munoz Marin Intl to Fort Lauderdale flights
Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Tampa flights
Santiago de los Caballeros to Newark flights
Luis Munoz Marin Intl to Philadelphia flights
Luis Munoz Marin Intl to Boston flights
Santo Domingo to Orlando flights
Aguadilla to Orlando flights
Santo Domingo to LaGuardia flights
Ponce to Orlando flights
Port of Spain to John F Kennedy Intl flights
Port of Spain to Miami flights
Santo Domingo to Boston flights
Luis Munoz Marin Intl to Atlanta flights
Luis Munoz Marin Intl to Midway flights
Santo Domingo to Miami flights
Luis Munoz Marin Intl to Hartford flights
Luis Munoz Marin Intl to Dallas/Fort Worth flights
Kingston to John F Kennedy Intl flights
Nassau to Fort Lauderdale flights
Nassau to Orlando flights
Luis Munoz Marin Intl to Hobby flights
Luis Munoz Marin Intl to Reagan-National flights
Luis Munoz Marin Intl to Las Vegas flights
Luis Munoz Marin Intl to George Bush Intcntl flights
Nassau to Miami flights
Luis Munoz Marin Intl to Baltimore flights
Montego Bay to John F Kennedy Intl flights
Santiago de los Caballeros to Orlando flights
Luis Munoz Marin Intl to Dulles Intl flights
Santiago de los Caballeros to LaGuardia flights
Luis Munoz Marin Intl to Denver flights
Bridgetown to John F Kennedy Intl flights
Kingston to Fort Lauderdale flights
Santo Domingo to Fort Lauderdale flights
Bridgetown to Miami flights
St. George's to John F Kennedy Intl flights
Luis Munoz Marin Intl to Austin flights
St. John's to John F Kennedy Intl flights
Punta Cana to John F Kennedy Intl flights
Luis Munoz Marin Intl to Raleigh flights
Kingston to Miami flights

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.