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Grand Cayman

$169+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$459
(American Airlines)

One-way from

$169
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$705
Provider with most accurate pricing for Chicago (CHI)-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-George Town Owen Roberts Intl flights.
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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 ($62 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This American Airlines deal was found by Cheapflights users on 4/30. 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.
Tue 6/36:47 pmSTL - GCM
1 stop16h 33mAmerican Airlines
Mon 6/92:05 pmGCM - STL
1 stop9h 54mAmerican Airlines
Deal found 4/30$459
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Sat 10/43:11 pmORD - GCM
1 stop20h 29mMultiple Airlines
Wed 10/811:30 amGCM - ORD
1 stop11h 17mMultiple Airlines
Deal found 4/30$464
This Justfly.com deal was found by Cheapflights users on 4/30. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/18:25 pmORD - GCM
1 stop15h 30mAir Canada
Thu 6/512:50 pmGCM - ORD
2 stops21h 02mAir Canada
Deal found 4/30$511
This Air Canada deal was found by Cheapflights users on 4/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/87:30 amSTL - GCM
1 stop28h 25mAir Canada
Thu 6/1212:50 pmGCM - STL
2 stops31h 08mAir Canada
Deal found 4/30$534
This Southwest deal was found by Cheapflights users on 4/30. 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.
Sun 7/205:05 amMDW - GCM
1 stop6h 45mSouthwest
Tue 7/2912:45 pmGCM - MDW
2 stops10h 15mSouthwest
Deal found 4/30$542
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Fri 8/16:37 pmMLI - GCM
2 stops15h 13mAmerican Airlines
Tue 8/1212:25 pmGCM - MLI
1 stop8h 45mAmerican Airlines
Deal found 4/30$542
This Delta deal was found by Cheapflights users on 4/30. 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.
Wed 7/25:35 amORD - GCM
1 stop5h 50mDelta
Fri 7/412:40 pmGCM - ORD
1 stop8h 44mDelta
Deal found 4/30$610
This Delta deal was found by Cheapflights users on 4/30. 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.
Mon 7/216:00 amMDW - GCM
1 stop5h 25mDelta
Tue 7/2912:40 pmGCM - MDW
1 stop9h 01mDelta
Deal found 4/30$610
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 5/285:00 amORD - GCM
1 stop6h 20mAmerican Airlines
Tue 6/312:10 pmGCM - ORD
2 stops11h 46mAmerican Airlines
Deal found 4/30$614
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 7/174:06 pmMDW - GCM
1 stop23h 54mMultiple Airlines
Sun 7/2712:40 pmGCM - MDW
1 stop9h 56mMultiple Airlines
Deal found 4/30$626
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Sat 5/319:26 amORD - GCM
Nonstop4h 04mUnited Airlines
Sat 6/71:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
Deal found 4/30$671
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Sat 6/218:05 amSTL - GCM
2 stops28h 25mUnited Airlines
Sat 6/284:45 pmGCM - STL
2 stops17h 55mUnited Airlines
Deal found 4/30$761

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 May 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

Tue 6/3

6:47 pm-11:20 am

1 stop16h 33m

George Town Owen Roberts Intl

Mon 6/9

2:05 pm-11:59 pm

1 stop9h 54m

$459

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 7/22

7:00 am-4:10 pm

1 stop9h 10m

George Town Owen Roberts Intl

Tue 7/29

11:30 am-8:51 am

1 stop21h 21m

$473

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 6/1

8:25 pm-11:55 am

1 stop15h 30m

George Town Owen Roberts Intl

Thu 6/5

12:50 pm-3:05 pm

1 stop26h 15m

$511

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Sun 6/8

7:30 am-11:55 am

1 stop28h 25m

George Town Owen Roberts Intl

Thu 6/12

12:50 pm-7:58 pm

2 stops31h 08m

$534

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 7/20

5:05 am-11:50 am

1 stop6h 45m

George Town Owen Roberts Intl

Tue 7/29

12:45 pm-11:00 pm

2 stops10h 15m

$542

MolineGeorge Town

MLI - GCM

MLIGCM

Moline Quad-City

Fri 8/1

6:37 pm-9:50 am

2 stops15h 13m

George Town Owen Roberts Intl

Tue 8/12

12:25 pm-9:10 pm

1 stop8h 45m

$542

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 7/2

5:35 am-11:25 am

1 stop5h 50m

George Town Owen Roberts Intl

Thu 7/10

12:40 pm-9:30 pm

1 stop8h 50m

$610

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 7/21

6:00 am-11:25 am

1 stop5h 25m

George Town Owen Roberts Intl

Fri 8/1

12:40 pm-9:41 pm

1 stop9h 01m

$610

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 5/28

5:00 am-11:20 am

1 stop6h 20m

George Town Owen Roberts Intl

Tue 6/3

12:10 pm-11:56 pm

2 stops11h 46m

$614

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 7/17

4:06 pm-4:00 pm

1 stop23h 54m

George Town Owen Roberts Intl

Sun 7/27

12:40 pm-10:36 pm

1 stop9h 56m

$626

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 24 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 May 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 May 1, 2025.
Read reviews from past customers who have flown Southwest, Delta and United Airlines from Illinois to Grand Cayman. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
WestJet
7.2
Good
2,826 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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?

    $217 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 Delta, with prices starting from $231 and $293, 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$446Average$684FlexibilityNo cancel feeOn-time71%
DeltaCheapest$463Average$668FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$501Average$705FlexibilityNo cancel feeOn-time69%

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