HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Illinois

$272+ 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — ORD
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
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 febrero 20, 2025.

Round-trip from

$453
(Kiwi.com)

One-way from

$272
(Mytrip)

Popular in

March

Cheapest in

September
From Grand Cayman to Illinois
Search Deals
One-way flight from Grand Cayman to Illinois
Search Deals
Highest demand for flights based on searches. 33% potential increase in price ($325 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($45 potential savings vs. average RT price).
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 febrero 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
vie. 5/304:45 pmGCM - ORD
1 stop16h 06mMultiple Airlines
lun. 6/27:00 amORD - GCM
1 stop9h 10mMultiple Airlines
Deal found 2/19$453
This JetBlue deal was found by Cheapflights users on 2/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/2012:10 pmGCM - ORD
1 stop22h 49mJetBlue
mié. 3/2611:44 amORD - GCM
1 stop23h 26mJetBlue
Deal found 2/19$525
This Gotogate deal was found by Cheapflights users on 2/19. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/203:00 pmGCM - ORD
2 stops19h 54mAir Canada
mié. 3/268:30 pmORD - GCM
1 stop17h 30mAir Canada
Deal found 2/19$556
This Southwest deal was found by Cheapflights users on 2/19. 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.
jue. 3/2012:40 pmGCM - MDW
1 stop7h 25mSouthwest
mié. 3/266:30 pmMDW - GCM
2 stops17h 15mSouthwest
Deal found 2/19$600
This American Airlines deal was found by Cheapflights users on 2/19. 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.
jue. 10/3012:45 pmGCM - ORD
1 stop11h 14mAmerican Airlines
dom. 11/25:01 amORD - GCM
2 stops8h 54mAmerican Airlines
Deal found 2/19$600
This Delta deal was found by Cheapflights users on 2/19. 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.
vie. 9/2612:56 pmGCM - ORD
1 stop8h 25mDelta
lun. 9/296:00 amORD - GCM
1 stop5h 31mDelta
Deal found 2/19$601
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/511:25 amGCM - MDW
1 stop11h 11mMultiple Airlines
sáb. 4/124:10 pmMDW - GCM
1 stop24h 00mMultiple Airlines
Deal found 2/18$619
This United Airlines deal was found by Cheapflights users on 2/19. 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.
sáb. 4/191:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
dom. 4/209:50 pmORD - GCM
1 stop14h 40mUnited Airlines
Deal found 2/19$670

Find flights from Grand Cayman to Illinois within your budget

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 febrero 20, 2025.

Fly from

Grand Cayman

Fly to

Illinois

Route

Depart

Return

Price

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

vie. 5/30

4:45 pm-8:51 am

1 stop16h 06m

Chicago O'Hare Intl

lun. 6/2

7:00 am-4:10 pm

1 stop9h 10m

$453

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

jue. 3/20

12:10 pm-10:59 am

1 stop22h 49m

Chicago O'Hare Intl

mié. 3/26

11:44 am-11:10 am

1 stop23h 26m

$525

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

jue. 3/20

3:00 pm-10:54 am

2 stops19h 54m

Chicago O'Hare Intl

mié. 3/26

8:30 pm-2:00 pm

1 stop17h 30m

$556

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

jue. 3/20

12:40 pm-8:05 pm

1 stop7h 25m

Chicago Midway

mié. 3/26

6:30 pm-11:45 am

2 stops17h 15m

$600

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

sáb. 4/5

11:25 am-10:36 pm

1 stop11h 11m

Chicago Midway

sáb. 4/12

4:10 pm-4:10 pm

1 stop24h 00m

$619

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

sáb. 4/19

1:45 pm-6:07 pm

Nonstop4h 22m

Chicago O'Hare Intl

dom. 4/20

9:50 pm-12:30 pm

1 stop14h 40m

$670

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

vie. 3/28

12:00 pm-10:16 pm

2 stops10h 16m

Chicago O'Hare Intl

lun. 3/31

6:05 am-2:34 pm

2 stops8h 29m

$1,142

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

jue. 5/29

11:30 am-8:51 am

1 stop21h 21m

$272

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

lun. 5/19

12:50 pm-8:02 am

2 stops19h 12m

$310

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mié. 3/19

1:50 pm-6:06 pm

Nonstop4h 16m

$387

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 12 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.

Travel insights for flights from Grand Cayman to Illinois

Get recent, data-driven insights about flights from Grand Cayman to Illinois including ideal travel times, pricing trends, and more.

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 febrero 20, 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.

Rainfall in Illinois by month

Plan your trip to Illinois by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.

Temperature in Illinois by month

Plan your trip to Illinois by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Illinois, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 febrero 20, 2025.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Air Canada, which is currently one of the cheapest options available, starting at $310. United Airlines flights start at $387 while deals on Delta start at $393 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 Newark flights
George Town to Orlando flights
George Town to Atlanta flights
George Town to Hobby flights
George Town to George Bush Intcntl flights
George Town to LaGuardia flights
George Town to Fort Lauderdale flights
George Town to Boston flights
George Town to Las Vegas flights
George Town to Tampa flights
George Town to O'Hare Intl flights
George Town to Los Angeles flights
George Town to Dallas/Fort Worth flights
George Town to West Palm Beach flights
George Town to Kansas City flights
George Town to New Orleans flights
George Town to San Francisco flights
George Town to Charlotte flights
George Town to Baltimore flights
George Town to Austin flights
George Town to Love Field flights
George Town to Dulles Intl flights
George Town to Melbourne flights
George Town to Columbus flights
George Town to Louisville flights
George Town to Denver flights
George Town to Savannah flights
George Town to San Diego flights
George Town to Portland flights
George Town to Traverse City flights
George Town to Salt Lake City flights
George Town to Jacksonville flights
George Town to Buffalo flights
George Town to Cleveland flights
George Town to Reagan-National flights
George Town to Sky Harbor Intl flights
George Town to Asheville flights
George Town to Boise flights
George Town to San Jose flights
George Town to Detroit flights
George Town to Honolulu 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.