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Grand Cayman

$193+ 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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Apr 14 — Apr 211
Mon 4/14
Mon 4/21
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 April 9, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$386
(American Airlines)

One-way from

$193
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$647
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. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 9, 2025.

This American Airlines deal was found by Cheapflights users on 4/8. 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 9/25:32 amSTL - GCM
1 stop7h 18mAmerican Airlines
Sun 9/712:45 pmGCM - STL
1 stop10h 38mAmerican Airlines
Deal found 4/8$386
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 10/253:11 pmORD - GCM
1 stop20h 29mMultiple Airlines
Tue 11/411:30 amGCM - ORD
1 stop12h 17mMultiple Airlines
Deal found 4/7$460
This Southwest deal was found by Cheapflights users on 4/7. 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.
Sat 5/105:35 amMDW - GCM
1 stop9h 15mSouthwest
Wed 5/1412:45 pmGCM - MDW
1 stop9h 20mSouthwest
Deal found 4/7$484
This Southwest deal was found by Cheapflights users on 4/8. 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.
Thu 5/159:10 pmSTL - GCM
2 stops14h 40mSouthwest
Mon 5/1912:45 pmGCM - STL
1 stop9h 10mSouthwest
Deal found 4/8$487
This Air Canada deal was found by Cheapflights users on 4/8. 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 6/18:25 pmORD - GCM
1 stop15h 30mAir Canada
Thu 6/512:50 pmGCM - ORD
2 stops21h 02mAir Canada
Deal found 4/8$524
This American Airlines deal was found by Cheapflights users on 4/8. 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
1 stop7h 11mAmerican Airlines
Deal found 4/8$610
This Delta deal was found by Cheapflights users on 4/6. 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.
Sun 10/266:00 amMDW - GCM
1 stop5h 42mDelta
Fri 10/311:02 pmGCM - MDW
1 stop8h 42mDelta
Deal found 4/6$610
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 5/224:11 pmMDW - GCM
1 stop23h 49mMultiple Airlines
Thu 5/2912:40 pmGCM - MDW
1 stop10h 01mMultiple Airlines
Deal found 4/7$634
This Mytrip deal was found by Cheapflights users on 4/8. 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.
Thu 5/1510:10 amSTL - GCM
3 stops25h 30mMultiple Airlines
Mon 5/194:45 pmGCM - STL
3 stops43h 00mMultiple Airlines
Deal found 4/8$637
This United Airlines deal was found by Cheapflights users on 4/7. 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 5/179:26 amORD - GCM
Nonstop4h 04mUnited Airlines
Sat 5/241:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
Deal found 4/7$645
This Delta deal was found by Cheapflights users on 4/6. 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.
Sat 10/256:00 amORD - GCM
1 stop5h 42mDelta
Mon 11/31:02 pmGCM - ORD
1 stop9h 10mDelta
Deal found 4/6$685
This United deal was found by Cheapflights users on 4/8. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/106:15 amSTL - GCM
1 stop6h 15mUnited Airlines
Wed 4/1612:55 pmGCM - STL
1 stop10h 20mUnited Airlines
Deal found 4/8$861

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 April 9, 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 9/2

5:32 am-12:50 pm

1 stop7h 18m

George Town Owen Roberts Intl

Sun 9/7

12:45 pm-11:23 pm

1 stop10h 38m

$386

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 4/29

7:00 pm-11:40 am

1 stop16h 40m

George Town Owen Roberts Intl

Mon 5/5

4:45 pm-6:00 pm

1 stop25h 15m

$468

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 5/10

5:35 am-2:50 pm

1 stop9h 15m

George Town Owen Roberts Intl

Wed 5/14

12:45 pm-10:05 pm

1 stop9h 20m

$484

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Thu 5/15

9:10 pm-11:50 am

2 stops14h 40m

George Town Owen Roberts Intl

Mon 5/19

12:45 pm-8:45 pm

2 stops8h 00m

$487

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-9:52 am

2 stops21h 02m

$524

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 6/15

5:25 pm-11:50 am

2 stops18h 25m

George Town Owen Roberts Intl

Fri 6/20

12:45 pm-9:25 am

2 stops20h 40m

$566

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-7:21 pm

1 stop7h 11m

$610

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 5/22

4:11 pm-4:00 pm

1 stop23h 49m

George Town Owen Roberts Intl

Thu 5/29

12:40 pm-10:41 pm

1 stop10h 01m

$634

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 8/30

6:00 am-11:31 am

1 stop5h 31m

George Town Owen Roberts Intl

Thu 9/4

12:50 pm-9:47 pm

1 stop8h 57m

$635

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Thu 5/15

10:10 am-11:40 am

3 stops25h 30m

George Town Owen Roberts Intl

Mon 5/19

4:45 pm-11:45 am

3 stops43h 00m

$637

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/6

Showing 1-10 of 20 results
1
2

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 April 9, 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 April 9, 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
4,281 reviews

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,281 reviews
Southwest
8.0
Very good
4,281 reviews

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,902 reviews
Southwest
8.0
Very good
4,281 reviews

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,633 reviews
Southwest
8.0
Very good
4,281 reviews

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,281 reviews

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Air Canada
7.0
Good
9,068 reviews
Southwest
8.0
Very good
4,281 reviews

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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?

    $193 is the cheapest one-way deal found within the past few days, from Sun Country Air. You may also be able to find cheap deals on Air Canada and Southwest, with prices starting from $224 and $241, 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 April 9, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$446Average$681FlexibilityNo cancel feeOn-time71%
DeltaCheapest$463Average$628FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$504Average$702FlexibilityNo cancel feeOn-time69%

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