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Grand Cayman

$179+ Cheap flights from Chicago (CHI) 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheap flight deals from Chicago to Grand Cayman

Keep the following information in mind while searching for Chicago to Grand Cayman flight deals. Data was last updated June 12, 2025.

Round-trip from

$467
(Mytrip)

One-way from

$179
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$655
From Chicago (CHI) to Grand Cayman
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One-way flight from Chicago (CHI) to Grand Cayman
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Highest demand for flights based on searches. 11% potential increase in price ($83 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 June 2025
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Find flight deals from Chicago to Grand Cayman

Cheapest flights from Chicago to Grand Cayman
Explore the most affordable flight options available from Chicago to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/11. 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.
Tue 7/81:43 pmORD - GCM
1 stop26h 27mMultiple Airlines
Mon 7/144:45 pmGCM - ORD
1 stop23h 26mMultiple Airlines
Deal found 6/11$467
This Southwest deal was found by Cheapflights users on 6/11. 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 11/17:20 pmMDW - GCM
2 stops17h 15mSouthwest
Thu 11/61:30 pmGCM - MDW
1 stop10h 20mSouthwest
Deal found 6/11$489
This Air Canada deal was found by Cheapflights users on 6/10. 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 10/196:20 pmORD - GCM
1 stop17h 35mAir Canada
Thu 10/3012:35 pmGCM - ORD
1 stop24h 16mAir Canada
Deal found 6/10$515
This Delta deal was found by Cheapflights users on 6/11. 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 12/106:00 amORD - GCM
1 stop5h 37mDelta
Tue 1/132:00 pmGCM - ORD
1 stop10h 54mDelta
Deal found 6/11$520
This Delta deal was found by Cheapflights users on 6/10. 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 10/196:00 amMDW - GCM
1 stop5h 42mDelta
Thu 10/301:02 pmGCM - MDW
1 stop8h 42mDelta
Deal found 6/10$520
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Sun 9/148:44 pmORD - GCM
1 stop14h 41mAmerican Airlines
Fri 9/1912:10 pmGCM - ORD
2 stops11h 02mAmerican Airlines
Deal found 6/11$524
This Southwest deal was found by Cheapflights users on 6/11. 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.
Wed 11/196:05 amORD - GCM
1 stop5h 30mSouthwest
Tue 12/21:30 pmGCM - ORD
1 stop9h 20mSouthwest
Deal found 6/11$543
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Wed 12/106:00 amORD - GCM
1 stop9h 25mUnited Airlines
Mon 1/122:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 6/11$600
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Fri 9/56:21 amMDW - GCM
1 stop9h 39mMultiple Airlines
Tue 9/911:30 amGCM - MDW
2 stops11h 28mMultiple Airlines
Deal found 6/10$654

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago 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 June 12, 2025.
Use the filters below to find and compare flights from Chicago to Grand Cayman that are best for you.

Fly from

Chicago

Fly to

Grand Cayman

Route

Depart

Return

Price

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 7/8

1:43 pm-4:10 pm

1 stop26h 27m

George Town Owen Roberts Intl

Mon 7/14

4:45 pm-4:11 pm

1 stop23h 26m

$467

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 11/1

7:20 pm-12:35 pm

2 stops17h 15m

George Town Owen Roberts Intl

Thu 11/6

1:30 pm-10:50 pm

1 stop10h 20m

$489

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 10/19

6:20 pm-11:55 am

1 stop17h 35m

George Town Owen Roberts Intl

Sun 10/26

12:35 pm-10:58 am

1 stop22h 23m

$515

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 10/20

6:00 am-11:42 am

1 stop5h 42m

George Town Owen Roberts Intl

Fri 10/24

1:02 pm-9:12 pm

1 stop8h 10m

$520

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 10/19

6:00 am-11:42 am

1 stop5h 42m

George Town Owen Roberts Intl

Thu 10/30

1:02 pm-9:44 pm

1 stop8h 42m

$520

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 9/14

8:44 pm-11:25 am

1 stop14h 41m

George Town Owen Roberts Intl

Fri 9/19

12:10 pm-11:12 pm

2 stops11h 02m

$524

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 11/19

6:05 am-12:35 pm

1 stop5h 30m

George Town Owen Roberts Intl

Tue 12/2

1:30 pm-9:50 pm

1 stop9h 20m

$543

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 10/19

6:00 am-12:30 pm

1 stop6h 30m

George Town Owen Roberts Intl

Wed 10/29

4:40 pm-12:15 am

1 stop7h 35m

$610

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 9/5

6:21 am-4:00 pm

1 stop9h 39m

George Town Owen Roberts Intl

Tue 9/9

11:30 am-10:58 pm

2 stops11h 28m

$654

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 7/17

5:30 pm-12:45 pm

2 stops43h 15m

George Town Owen Roberts Intl

Tue 7/22

1:45 pm-4:44 pm

2 stops50h 59m

$804

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 18 results
1
2

Best time to book a flight from Chicago to Grand Cayman

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

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Grand Cayman (average of $467). Flying from Chicago 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 CHI to LAW?

Find hourly flight availability from Chicago 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 June 12, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago 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 June 12, 2025.
Get a feel of what it's like to fly with Southwest, Delta and United Airlines from Chicago to Grand Cayman by reading reviews from past customers. 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
4,287 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
WestJet
7.2
Good
2,868 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

Find useful and relevant information for your journey from Chicago 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 Chicago to Grand Cayman one-way?

    For one-way options, check prices for Air Canada. According to our data, you can fly for as low as $237. Users have also found prices from $281 and $313 on Southwest and American Airlines, respectively.

  • What are the cheapest flights from Chicago to Grand Cayman?

    On average you can expect to pay $543 for a flight from Chicago to Grand Cayman. The cheapest flight overall is $288 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $467.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago to Grand Cayman (average of $467). Flying from Chicago 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

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 Chicago to Grand Cayman

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to George Town flights
Midway to George Town flights
St. Louis to George Town flights
Moline to George Town flights
O'Hare Intl to Cayman Brac flights

Top 3 airlines flying from Chicago to Grand Cayman

Discover the top 3 airlines that operate flights from Chicago 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$463Average$668FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$468Average$661FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$522Average$721FlexibilityNo cancel feeOn-time69%

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