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Cayman Islands

$124+ Cheap flights from Chicago (CHI) to the Cayman Islands

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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
1 adult, Economy
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Cheap flight deals from Chicago to Cayman Islands

Keep the following information in mind while searching for Chicago to Cayman Islands flight deals. Data was last updated septiembre 15, 2025.

Round-trip from

$311
(Priceline)

One-way from

$124
(Priceline)

Popular in

December

Cheapest in

October

Average price

$569

Good round-trip deal

$530 or less

Good one-way deal

$582 or less
From Chicago (CHI) to Cayman Islands
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One-way flight from Chicago (CHI) to Cayman Islands
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Highest demand for flights based on searches. 8% potential increase in price ($59 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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Price to beat on a round-trip flight from Chicago (CHI) to Cayman Islands.
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Price to beat on a one-way flight from Chicago (CHI) to Cayman Islands.
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Find flight deals from Chicago to Cayman Islands

Cheapest flights from Chicago to Cayman Islands
Explore the most affordable flight options available from Chicago to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 15, 2025.

This Southwest deal was found by Cheapflights users on 9/12. 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.
mié. 11/126:05 amORD - GCM
1 stop5h 30mSouthwest
jue. 11/201:30 pmGCM - ORD
1 stop9h 20mSouthwest
Deal found 9/12$426
This Air Canada deal was found by Cheapflights users on 9/12. 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.
jue. 11/138:15 pmORD - GCM
1 stop15h 10mAir Canada
vie. 11/211:30 pmGCM - ORD
1 stop9h 35mAir Canada
Deal found 9/12$430
This JetBlue deal was found by Cheapflights users on 9/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/146:55 pmORD - GCM
1 stop15h 59mJetBlue
dom. 11/233:36 pmGCM - ORD
1 stop8h 14mJetBlue
Deal found 9/13$431
This Booking.com deal was found by Cheapflights users on 9/13. 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.
mar. 10/287:20 amORD - GCM
2 stops52h 05mAir Canada
jue. 11/61:30 pmGCM - ORD
1 stop26h 40mAir Canada
Deal found 9/13$438
This Booking.com deal was found by Cheapflights users on 9/14. 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.
mar. 12/26:05 pmORD - GCM
2 stops41h 20mAir Canada
mar. 12/91:30 pmGCM - ORD
2 stops43h 31mAir Canada
Deal found 9/14$439
This American Airlines deal was found by Cheapflights users on 9/14. 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.
mar. 10/145:20 amORD - GCM
1 stop6h 00mAmerican Airlines
mar. 10/2112:10 pmGCM - ORD
1 stop9h 13mAmerican Airlines
Deal found 9/14$446
This American Airlines deal was found by Cheapflights users on 9/13. 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.
sáb. 9/276:55 pmORD - GCM
1 stop16h 27mAmerican Airlines
mar. 9/3012:10 pmGCM - ORD
2 stops19h 32mAmerican Airlines
Deal found 9/13$450
This Southwest deal was found by Cheapflights users on 9/14. 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.
dom. 12/75:50 amMDW - GCM
1 stop5h 45mSouthwest
vie. 12/121:30 pmGCM - MDW
2 stops11h 00mSouthwest
Deal found 9/14$450
This Delta deal was found by Cheapflights users on 9/13. 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.
dom. 11/167:52 pmORD - GCM
1 stop15h 43mDelta
vie. 11/211:50 pmGCM - ORD
1 stop11h 12mDelta
Deal found 9/13$452
This Delta deal was found by Cheapflights users on 9/12. 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.
mié. 11/125:32 amORD - GCM
1 stop6h 03mDelta
mié. 11/191:50 pmGCM - ORD
2 stops19h 16mDelta
Deal found 9/12$456
This American Airlines deal was found by Cheapflights users on 9/13. 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.
sáb. 11/157:07 pmORD - GCM
1 stop16h 04mAmerican Airlines
sáb. 11/223:50 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 9/13$467
This American Airlines deal was found by Cheapflights users on 9/13. 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.
sáb. 10/186:36 pmORD - GCM
1 stop16h 49mAmerican Airlines
sáb. 10/2512:10 pmGCM - ORD
1 stop7h 22mAmerican Airlines
Deal found 9/13$471

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Cayman Islands 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 septiembre 15, 2025.
Use the filters below to find and compare flights from Chicago to the Cayman Islands that are best for you.

Fly from

Chicago

Fly to

Cayman Islands

Route

Depart

Return

Price

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 11/12

6:05 am-12:35 pm

1 stop5h 30m

George Town Owen Roberts Intl

jue. 11/20

1:30 pm-9:50 pm

1 stop9h 20m

$426

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

vie. 11/14

6:55 pm-11:54 am

1 stop15h 59m

George Town Owen Roberts Intl

vie. 11/21

3:43 pm-10:50 pm

1 stop8h 07m

$431

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

vie. 11/14

6:55 pm-11:54 am

1 stop15h 59m

George Town Owen Roberts Intl

dom. 11/23

3:36 pm-10:50 pm

1 stop8h 14m

$431

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

dom. 12/7

9:40 pm-12:35 pm

2 stops13h 55m

George Town Owen Roberts Intl

vie. 12/12

1:30 pm-12:10 am

2 stops11h 40m

$450

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

dom. 11/16

7:52 pm-12:35 pm

1 stop15h 43m

George Town Owen Roberts Intl

vie. 11/21

1:50 pm-12:02 am

1 stop11h 12m

$452

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

jue. 12/4

8:49 am-4:30 pm

1 stop6h 41m

George Town Owen Roberts Intl

mar. 12/9

5:45 pm-12:15 am

1 stop7h 30m

$452

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

lun. 12/15

7:35 am-4:30 pm

1 stop7h 55m

George Town Owen Roberts Intl

vie. 12/19

2:50 pm-6:04 pm

Nonstop4h 14m

$476

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

dom. 11/16

7:52 pm-12:35 pm

1 stop15h 43m

George Town Owen Roberts Intl

dom. 11/23

1:50 pm-12:02 am

1 stop11h 12m

$477

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

jue. 11/6

5:50 am-12:35 pm

1 stop5h 45m

George Town Owen Roberts Intl

mar. 11/11

1:30 pm-10:35 pm

2 stops10h 05m

$520

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

vie. 11/7

6:05 pm-1:00 pm

2 stops17h 55m

George Town Owen Roberts Intl

mar. 11/11

1:30 pm-10:35 pm

2 stops10h 05m

$540

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 25 results
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Best time to book a flight from Chicago to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands 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 the Cayman Islands

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

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

Find hourly flight availability from Chicago to Cayman Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 15, 2025.

When flying from Chicago to Cayman Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Cayman Islands

Get insights into the airlines that provide service to Cayman Islands. 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 Cayman Islands. Reviews last updated septiembre 15, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Chicago to the Cayman Islands. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

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
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

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
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

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
4,242 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

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 Cayman Islands. 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 Cayman Islands?

    A quick flight from Chicago to Cayman Islands can take about 5h 30m. Southwest provides one of the quickest options available for as low as $426. Airlines will cover a distance of 1613 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $124. However, be on the lookout for offers from Air Canada and JetBlue, as they are both options that can get you from Chicago to Cayman Islands for a low price.

  • What are the most popular routes from Chicago to Cayman Islands?

    When deciding which route to take from Chicago to Cayman Islands consider Chicago O'Hare Intl - George Town Owen Roberts Intl, Chicago Midway - George Town Owen Roberts Intl or Chicago O'Hare Intl - Cayman Brac Gerrard-Smith as they are the most popular.

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

    On average you can expect to pay $626 for a flight from Chicago to Cayman Islands. The cheapest flight overall is $505 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $443.

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

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

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

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

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

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

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

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Chicago to Cayman Islands

Discover the top 3 airlines that operate flights from Chicago to Cayman Islands. 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 septiembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$530Average$696FlexibilityNo cancel feeOn-time71%
DeltaCheapest$564Average$694FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$587Average$751FlexibilityNo cancel feeOn-time69%

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