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Grand Cayman

$174+ Cheap flights from Illinois to Grand Cayman

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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
ago. 6 — ago. 131
mié. 8/6
mié. 8/13
1 adult, Economy
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Cheap flight deals from Illinois to Grand Cayman

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

Round-trip from

$425
(American Airlines)

One-way from

$174
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$719
From Illinois to Grand Cayman
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One-way flight from Illinois to Grand Cayman
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Highest demand for flights based on searches. 8% potential increase in price ($60 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Illinois to Grand Cayman

Cheapest flights from Illinois to Grand Cayman
Explore the most affordable flight options available from Illinois to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 1, 2025.

This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/255:26 amSTL - GCM
1 stop7h 46mAmerican Airlines
sáb. 8/302:15 pmGCM - STL
1 stop8h 59mAmerican Airlines
Deal found 7/30$425
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/152:00 pmORD - GCM
1 stop21h 55mAir Canada
lun. 10/2012:50 pmGCM - ORD
1 stop20h 23mAir Canada
Deal found 7/31$459
This Kiwi.com deal was found by Cheapflights users on 8/1. 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.
lun. 9/1510:27 amORD - GCM
1 stop29h 43mMultiple Airlines
lun. 9/224:45 pmGCM - ORD
1 stop16h 33mMultiple Airlines
Deal found 8/1$464
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/2310:10 pmORD - GCM
2 stops13h 00mAmerican Airlines
sáb. 8/3012:10 pmGCM - ORD
1 stop10h 31mAmerican Airlines
Deal found 7/30$481
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.
vie. 11/73:15 pmSTL - GCM
2 stops20h 45mSouthwest
mar. 11/111:30 pmGCM - STL
2 stops9h 40mSouthwest
Deal found 7/30$485
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/158:50 amORD - GCM
2 stops28h 41mJetBlue
sáb. 11/221:57 pmGCM - ORD
1 stop22h 59mJetBlue
Deal found 7/30$489
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.
sáb. 11/294:05 pmSTL - GCM
1 stop19h 15mAir Canada
vie. 12/51:30 pmGCM - STL
1 stop26h 59mAir Canada
Deal found 7/31$502
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.
dom. 12/147:35 amORD - GCM
1 stop7h 55mUnited Airlines
vie. 12/192:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 7/31$510
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/245:40 amORD - GCM
1 stop5h 50mDelta
mar. 12/301:55 pmGCM - ORD
1 stop8h 32mDelta
Deal found 7/31$520
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.
dom. 12/146:00 amMDW - GCM
1 stop5h 37mDelta
vie. 12/192:02 pmGCM - MDW
1 stop8h 42mDelta
Deal found 7/30$520
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/149:05 pmMDW - GCM
2 stops14h 30mSouthwest
vie. 12/191:30 pmGCM - MDW
1 stop8h 05mSouthwest
Deal found 7/31$524
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/296:30 amSTL - GCM
1 stop6h 15mUnited Airlines
sáb. 12/62:25 pmGCM - STL
1 stop10h 17mUnited Airlines
Deal found 7/30$536

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Grand Cayman 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 agosto 1, 2025.
Use the filters below to find and compare flights from Illinois to Grand Cayman that are best for you.

Fly from

Illinois

Fly to

Grand Cayman

Route

Depart

Return

Price

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

lun. 8/25

5:26 am-1:12 pm

1 stop7h 46m

George Town Owen Roberts Intl

sáb. 8/30

2:15 pm-11:14 pm

1 stop8h 59m

$425

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

lun. 1/12

7:55 pm-12:55 pm

2 stops16h 00m

George Town Owen Roberts Intl

mié. 1/21

1:50 pm-9:00 pm

1 stop8h 10m

$438

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

lun. 1/12

6:05 am-12:55 pm

1 stop5h 50m

George Town Owen Roberts Intl

mié. 1/21

1:50 pm-9:50 pm

1 stop9h 00m

$448

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 10/15

2:00 pm-11:55 am

1 stop21h 55m

George Town Owen Roberts Intl

lun. 10/20

12:50 pm-9:13 am

1 stop20h 23m

$459

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

lun. 9/15

10:27 am-4:10 pm

1 stop29h 43m

George Town Owen Roberts Intl

lun. 9/22

4:45 pm-9:18 am

1 stop16h 33m

$464

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

sáb. 8/23

10:10 pm-11:10 am

2 stops13h 00m

George Town Owen Roberts Intl

sáb. 8/30

12:10 pm-10:41 pm

1 stop10h 31m

$481

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

vie. 11/7

3:15 pm-1:00 pm

2 stops20h 45m

George Town Owen Roberts Intl

mar. 11/11

1:30 pm-10:10 pm

2 stops9h 40m

$485

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

sáb. 11/15

8:50 am-2:31 pm

2 stops28h 41m

George Town Owen Roberts Intl

sáb. 11/22

1:57 pm-11:56 am

1 stop22h 59m

$489

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

sáb. 11/29

4:05 pm-12:20 pm

1 stop19h 15m

George Town Owen Roberts Intl

vie. 12/5

1:30 pm-3:29 pm

1 stop26h 59m

$502

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

dom. 12/14

7:35 am-4:30 pm

1 stop7h 55m

George Town Owen Roberts Intl

vie. 12/19

2:50 pm-6:04 pm

Nonstop4h 14m

$510

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 28 results
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Best time to book a flight from Illinois to Grand Cayman

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

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

Currently, January is the cheapest month in which you can book a flight from Illinois to Grand Cayman (average of $467). Flying from Illinois to Grand Cayman in March is currently the most expensive (average of $594). 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 LAW?

Find hourly flight availability from Illinois to Grand Cayman. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated agosto 1, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Grand Cayman as you normally would.

Reviews of airlines servicing Grand Cayman

Get insights into the airlines that provide service to Grand Cayman. 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 Grand Cayman. Reviews last updated agosto 1, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Illinois to Grand Cayman. 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

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

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

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

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

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

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

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

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.
JetBlue
7.3
Good
2,914 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

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

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

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 Illinois to Grand Cayman. 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 Illinois to Grand Cayman one-way?

    $178 is the cheapest one-way deal found within the past few days, from Air Canada. You may also be able to find cheap deals on Southwest and American Airlines, with prices starting from $208 and $260, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Illinois to Grand Cayman 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 Grand Cayman?

    Currently, January is the cheapest month in which you can book a flight from Illinois to Grand Cayman (average of $467). Flying from Illinois to Grand Cayman in March is currently the most expensive (average of $594). 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

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Alternative routes for Illinois to Grand Cayman

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Illinois to Grand Cayman

Discover the top 3 airlines that operate flights from Illinois to Grand Cayman. 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 agosto 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$463Average$668FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$512Average$683FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$573Average$732FlexibilityNo cancel feeOn-time69%

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