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Grand Cayman

$164+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
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 August 18, 2025.

Round-trip from

$377
(FlightHub)

One-way from

$164
(Southwest)

Popular in

March

Cheapest in

October

Average price

$739
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. 7% potential increase in price ($56 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 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 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 August 18, 2025.

This Vliegwinkel deal was found by Cheapflights users on 8/17. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/1412:00 pmORD - GCM
1 stop23h 55mAir Canada
Mon 9/2212:50 pmGCM - ORD
1 stop22h 03mAir Canada
Deal found 8/17$413
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Wed 9/1010:27 amORD - GCM
1 stop25h 13mMultiple Airlines
Fri 9/124:45 pmGCM - ORD
1 stop16h 33mMultiple Airlines
Deal found 8/16$451
This Booking.com deal was found by Cheapflights users on 8/18. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/128:25 pmORD - GCM
1 stop15h 30mAir Canada
Mon 10/2012:50 pmGCM - ORD
1 stop24h 24mAir Canada
Deal found 8/18$462
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Tue 9/1610:27 amORD - GCM
1 stop29h 43mMultiple Airlines
Tue 9/2311:30 amGCM - ORD
1 stop21h 48mMultiple Airlines
Deal found 8/17$463
This Mytrip deal was found by Cheapflights users on 8/17. 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 10/210:27 amORD - GCM
1 stop10h 53mMultiple Airlines
Thu 10/94:45 pmGCM - ORD
1 stop16h 37mMultiple Airlines
Deal found 8/17$467
This Mytrip deal was found by Cheapflights users on 8/16. 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 9/2510:27 amORD - GCM
1 stop10h 53mMultiple Airlines
Mon 9/294:45 pmGCM - ORD
1 stop16h 33mMultiple Airlines
Deal found 8/16$468
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/1610:27 amORD - GCM
1 stop10h 53mMultiple Airlines
Mon 10/204:45 pmGCM - ORD
1 stop16h 37mMultiple Airlines
Deal found 8/17$474
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Wed 10/1510:27 amORD - GCM
1 stop25h 13mMultiple Airlines
Sun 10/194:45 pmGCM - ORD
1 stop16h 37mMultiple Airlines
Deal found 8/16$483
This Southwest deal was found by Cheapflights users on 8/16. 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 12/149:05 pmMDW - GCM
2 stops14h 30mSouthwest
Fri 12/191:30 pmGCM - MDW
2 stops10h 35mSouthwest
Deal found 8/16$497
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Sun 9/146:21 amMDW - GCM
1 stop10h 59mMultiple Airlines
Mon 9/227:00 amGCM - MDW
2 stops11h 43mMultiple Airlines
Deal found 8/17$544
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 9/196:21 amMDW - GCM
1 stop9h 39mMultiple Airlines
Sun 9/217:00 amGCM - MDW
2 stops24h 11mMultiple Airlines
Deal found 8/17$549
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 10/235:56 pmMDW - GCM
2 stops17h 44mMultiple Airlines
Wed 10/295:10 pmGCM - MDW
1 stop30h 15mMultiple Airlines
Deal found 8/16$560

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 August 18, 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

Sat 1/31

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Sat 2/7

11:55 am-11:42 pm

1 stop12h 47m

$377

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/24

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Sat 1/31

11:55 am-9:00 pm

1 stop10h 05m

$377

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 9/14

12:00 pm-11:55 am

1 stop23h 55m

George Town Owen Roberts Intl

Mon 9/22

12:50 pm-10:53 am

1 stop22h 03m

$413

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 2/7

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Sat 2/14

11:55 am-9:00 pm

1 stop10h 05m

$443

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 9/10

10:27 am-11:40 am

1 stop25h 13m

George Town Owen Roberts Intl

Fri 9/12

4:45 pm-9:18 am

1 stop16h 33m

$451

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 2/4

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Sun 2/8

11:55 am-9:00 pm

1 stop10h 05m

$455

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 10/12

8:25 pm-11:55 am

1 stop15h 30m

George Town Owen Roberts Intl

Mon 10/20

12:50 pm-1:14 pm

1 stop24h 24m

$462

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 1/26

5:00 am-12:55 pm

1 stop6h 55m

George Town Owen Roberts Intl

Fri 1/30

1:50 pm-9:00 pm

1 stop8h 10m

$476

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 12/14

9:05 pm-12:35 pm

2 stops14h 30m

George Town Owen Roberts Intl

Fri 12/19

1:30 pm-11:05 pm

2 stops10h 35m

$497

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 9/14

6:21 am-5:20 pm

1 stop10h 59m

George Town Owen Roberts Intl

Mon 9/22

7:00 am-6:43 pm

2 stops11h 43m

$544

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

Showing 1-10 of 23 results
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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 August 18, 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 August 18, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Chicago to Grand Cayman. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,925 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

  • How long is the flight from Chicago to Grand Cayman?

    A quick flight from Chicago to Grand Cayman can take about 6h 55m. Spirit Airlines provides one of the quickest options available for as low as $476. The distance between Chicago and Grand Cayman is about 1598 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Grand Cayman one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $164. Users have also found prices from $172 and $429 on JetBlue and Delta, respectively.

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

    On average you can expect to pay $637 for a flight from Chicago to Grand Cayman. The cheapest flight overall is $313 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $377.

  • 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

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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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$463Average$668FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$512Average$685FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$573Average$735FlexibilityNo cancel feeOn-time69%

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