HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Illinois

$264+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — ORD
Aug 6 — Aug 131
Wed 8/6
Wed 8/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Grand Cayman 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 Grand Cayman to Illinois

Keep the following information in mind while searching for Grand Cayman to Illinois flight deals. Data was last updated August 1, 2025.

Round-trip from

$410
(Southwest)

One-way from

$264
(Southwest)
From Grand Cayman to Illinois
Search Deals
One-way flight from Grand Cayman to Illinois
Search Deals

Find 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 August 1, 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 7/31. 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
1 stop20h 23mAir Canada
Sun 10/193:35 pmORD - GCM
2 stops20h 20mAir Canada
Deal found 7/31$450
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 9/154:45 pmGCM - ORD
1 stop16h 33mMultiple Airlines
Mon 9/2210:27 amORD - GCM
1 stop10h 53mMultiple Airlines
Deal found 7/31$474
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 Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/142:02 pmGCM - MDW
1 stop8h 42mDelta
Sun 11/166:00 amMDW - GCM
1 stop5h 37mDelta
Deal found 7/30$511
This American Airlines deal was found by Cheapflights users on 7/31. 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 9/312:10 pmGCM - ORD
2 stops19h 32mAmerican Airlines
Sat 9/68:29 pmORD - GCM
2 stops14h 41mAmerican Airlines
Deal found 7/31$624
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 8/1412:40 pmGCM - MDW
1 stop9h 44mMultiple Airlines
Sun 8/173:58 pmMDW - GCM
1 stop25h 22mMultiple Airlines
Deal found 7/31$752
This United Airlines deal was found by Cheapflights users on 7/31. 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 8/161:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
Mon 8/186:00 amORD - GCM
1 stop6h 30mUnited Airlines
Deal found 7/31$899
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1612:55 pmGCM - ORD
1 stop11h 02mDelta
Sun 10/195:20 amORD - GCM
1 stop6h 15mDelta
Deal found 7/30$2,211

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 August 1, 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 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-9:13 am

1 stop20h 23m

Chicago O'Hare Intl

Sun 10/19

3:35 pm-11:55 am

2 stops20h 20m

$450

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 9/15

4:45 pm-9:18 am

1 stop16h 33m

Chicago O'Hare Intl

Mon 9/22

10:27 am-9:20 pm

1 stop10h 53m

$474

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

Fri 11/14

2:02 pm-9:44 pm

1 stop8h 42m

Chicago Midway

Sun 11/16

6:00 am-12:37 pm

1 stop5h 37m

$511

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 9/3

12:10 pm-7:42 am

2 stops19h 32m

Chicago O'Hare Intl

Sat 9/6

8:29 pm-11:10 am

2 stops14h 41m

$624

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 8/14

12:40 pm-10:24 pm

1 stop9h 44m

Chicago Midway

Sun 8/17

3:58 pm-5:20 pm

1 stop25h 22m

$752

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 8/16

1:45 pm-6:07 pm

Nonstop4h 22m

Chicago O'Hare Intl

Mon 8/18

6:00 am-12:30 pm

1 stop6h 30m

$899

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 10/16

12:55 pm-11:57 pm

1 stop11h 02m

Chicago O'Hare Intl

Sun 10/19

5:20 am-11:35 am

1 stop6h 15m

$2,211

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 1/14

1:50 pm-9:50 pm

1 stop9h 00m

$264

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 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 August 1, 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 August 1, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United 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.
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Air Canada
7.1
Good
9,851 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

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

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $264. Air Canada flights start at $275 while deals on American Airlines start at $387 one-way.

  • 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.

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

    Currently, August is the cheapest month in which you can book a flight from Grand Cayman to Illinois (average of $245). Flying from Grand Cayman 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 Grand Cayman to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
George Town to Miami flights
George Town to John F Kennedy Intl flights
George Town to Los Angeles flights
George Town to Atlanta flights
George Town to LaGuardia flights
George Town to Newark flights
George Town to Orlando flights
George Town to Tampa flights
George Town to Boise flights
George Town to Dallas/Fort Worth flights
George Town to Fort Lauderdale flights
George Town to Austin flights
George Town to Boston flights
George Town to O'Hare Intl flights
George Town to Denver flights
George Town to Salt Lake City flights
George Town to Buffalo flights
George Town to Las Vegas flights
George Town to Dulles Intl flights
George Town to Melbourne flights
George Town to New Orleans flights
George Town to Hobby flights
George Town to Sky Harbor Intl flights
George Town to San Francisco flights
George Town to Traverse City flights
George Town to George Bush Intcntl flights
George Town to Asheville flights
George Town to West Palm Beach flights
George Town to New Haven flights
George Town to Baltimore flights
George Town to Cleveland flights
George Town to Love Field flights
George Town to Louisville flights
George Town to Portland flights
George Town to San Diego flights
George Town to Savannah flights
George Town to Columbus flights
George Town to San Jose flights
George Town to Charlotte flights
George Town to Reagan-National flights
George Town to Manchester flights
George Town to Detroit flights
George Town to Kansas City 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.