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Grand Cayman

$124+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$311
(Priceline)

One-way from

$124
(Priceline)

Popular in

March

Cheapest in

October

Average price

$569
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 ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:59 pmORD - GCM
1 stop16h 01mSpirit Airlines
Sat 12/1311:55 amGCM - ORD
1 stop10h 05mSpirit Airlines
Deal found 9/10$311
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/55:59 pmORD - GCM
1 stop16h 01mMultiple Airlines
Tue 12/91:30 pmGCM - ORD
2 stops19h 30mMultiple Airlines
Deal found 9/10$369
This Expedia deal was found by Cheapflights users on 9/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:05 pmORD - GCM
2 stops41h 20mMultiple Airlines
Sun 12/1411:55 amGCM - ORD
1 stop12h 47mMultiple Airlines
Deal found 9/11$374
This Air Canada deal was found by Cheapflights users on 9/9. 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.
Thu 11/206:05 pmORD - GCM
2 stops17h 20mAir Canada
Thu 11/271:30 pmGCM - ORD
2 stops19h 31mAir Canada
Deal found 9/9$380
This Air Canada deal was found by Cheapflights users on 9/9. 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.
Sat 11/228:15 pmORD - GCM
1 stop15h 10mAir Canada
Fri 11/281:30 pmGCM - ORD
2 stops24h 21mAir Canada
Deal found 9/9$402
This Mytrip deal was found by Cheapflights users on 9/8. 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.
Wed 10/1511:13 amORD - GCM
2 stops24h 22mMultiple Airlines
Mon 10/2012:50 pmGCM - ORD
1 stop26h 14mMultiple Airlines
Deal found 9/8$444
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/119:27 amORD - GCM
1 stop26h 08mMultiple Airlines
Sun 10/194:45 pmGCM - ORD
1 stop16h 37mMultiple Airlines
Deal found 9/8$446
This American Airlines deal was found by Cheapflights users on 9/8. 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 10/155:20 amORD - GCM
1 stop6h 00mAmerican Airlines
Tue 10/2112:10 pmGCM - ORD
2 stops11h 40mAmerican Airlines
Deal found 9/8$450
This Mytrip deal was found by Cheapflights users on 9/8. 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.
Wed 10/1511:13 amORD - GCM
2 stops24h 22mMultiple Airlines
Sun 10/194:45 pmGCM - ORD
1 stop16h 37mMultiple Airlines
Deal found 9/8$452
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/55:05 amMDW - GCM
1 stop6h 30mSouthwest
Tue 12/91:30 pmGCM - MDW
1 stop8h 10mSouthwest
Deal found 9/10$454
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1210:27 amORD - GCM
1 stop25h 08mMultiple Airlines
Sun 10/194:45 pmGCM - ORD
1 stop16h 37mMultiple Airlines
Deal found 9/8$461
This United Airlines deal was found by Cheapflights users on 9/9. 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.
Sun 11/96:00 amORD - GCM
1 stop9h 30mUnited Airlines
Sat 11/222:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 9/9$467

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 September 11, 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 12/6

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Sat 12/13

11:55 am-9:00 pm

1 stop10h 05m

$311

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 12/5

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Tue 12/9

1:30 pm-5:48 pm

1 stop29h 18m

$369

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 11/20

8:15 pm-12:25 pm

1 stop15h 10m

George Town Owen Roberts Intl

Fri 11/28

1:30 pm-8:01 am

2 stops19h 31m

$380

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 10/11

9:27 am-11:35 am

1 stop26h 08m

George Town Owen Roberts Intl

Sun 10/19

4:45 pm-9:22 am

1 stop16h 37m

$446

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 10/15

5:20 am-11:20 am

1 stop6h 00m

George Town Owen Roberts Intl

Tue 10/21

12:10 pm-11:50 pm

2 stops11h 40m

$450

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 12/5

5:05 am-12:35 pm

1 stop6h 30m

George Town Owen Roberts Intl

Tue 12/9

1:30 pm-8:40 pm

1 stop8h 10m

$454

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 11/1

6:36 pm-11:57 am

1 stop17h 21m

George Town Owen Roberts Intl

Sat 11/8

4:01 pm-7:11 pm

Nonstop4h 10m

$468

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 12/6

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Sat 12/20

11:55 am-9:00 pm

1 stop10h 05m

$471

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 9/27

7:15 pm-11:10 am

1 stop15h 55m

George Town Owen Roberts Intl

Sat 10/4

12:10 pm-10:26 pm

1 stop10h 16m

$471

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 9/25

8:45 pm-11:25 am

1 stop14h 40m

George Town Owen Roberts Intl

Tue 9/30

12:10 pm-10:26 pm

1 stop10h 16m

$471

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 31 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 September 11, 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 September 11, 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
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 30m. Spirit Airlines provides one of the quickest options available for as low as $454. The distance between Chicago and Grand Cayman is about 1598 mi. This flight may include one or multiple stops.

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

    On average you can expect to pay $626 for a flight from Chicago to Grand Cayman. The cheapest flight overall is $505 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $311.

  • 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

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$530Average$690FlexibilityNo cancel feeOn-time71%
DeltaCheapest$564Average$694FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$588Average$749FlexibilityNo cancel feeOn-time69%

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