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Cayman Islands

$72+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Wed 12/316:05 pmORD - GCM
1 stop16h 30mMultiple Airlines
Wed 1/711:30 amGCM - ORD
1 stop21h 48mMultiple Airlines
Deal found 12/17$368
This United Airlines deal was found by Cheapflights users on 12/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Wed 12/312:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 12/17$438
This Delta deal was found by Cheapflights users on 12/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:30 amORD - GCM
1 stop6h 06mDelta
Wed 12/313:42 pmGCM - ORD
1 stop9h 20mDelta
Deal found 12/16$452
This American Airlines deal was found by Cheapflights users on 12/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/249:24 amORD - GCM
Nonstop4h 11mAmerican Airlines
Wed 12/313:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 12/18$463
This United Airlines deal was found by Cheapflights users on 12/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/188:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Thu 12/252:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 12/17$468
This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Mon 12/295:10 pmGCM - ORD
1 stop7h 34mUnited Airlines
Deal found 12/16$478
This Delta deal was found by Cheapflights users on 12/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/255:30 amORD - GCM
1 stop7h 57mDelta
Wed 12/311:52 pmGCM - ORD
1 stop11h 10mDelta
Deal found 12/16$482
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/259:24 amORD - GCM
Nonstop4h 11mAmerican Airlines
Wed 12/313:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 12/16$493
This Southwest deal was found by Cheapflights users on 12/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/185:50 amMDW - GCM
1 stop5h 45mSouthwest
Thu 12/251:30 pmGCM - MDW
1 stop8h 10mSouthwest
Deal found 12/17$522
This Delta deal was found by Cheapflights users on 12/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:00 amMDW - GCM
1 stop5h 36mDelta
Wed 12/311:52 pmGCM - MDW
1 stop9h 30mDelta
Deal found 12/17$559
This Delta deal was found by Cheapflights users on 12/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:00 amMDW - GCM
1 stop7h 27mDelta
Wed 12/313:42 pmGCM - MDW
1 stop7h 40mDelta
Deal found 12/17$651
This Delta deal was found by Cheapflights users on 12/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:00 amMDW - GCM
1 stop7h 27mDelta
Thu 1/13:42 pmGCM - MDW
1 stop7h 40mDelta
Deal found 12/17$723

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$240
(Mytrip)

One-way from

$72
(Priceline)

Popular in

December

Cheapest in

October

Average price

$827

Good round-trip deal

$449 or less

Good one-way deal

$288 or less
Provider with most accurate pricing for Chicago (CHI)-George Town Owen Roberts Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-George Town Owen Roberts Intl flights.
Search Deals
From Chicago (CHI) to Cayman Islands
Search Deals
One-way flight from Chicago (CHI) to Cayman Islands
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Cayman Islands.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Cayman Islands.
Search Deals

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 December 18, 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

Sat 3/28

3:55 pm-11:10 am

1 stop19h 15m

George Town Owen Roberts Intl

Fri 4/3

12:30 pm-10:03 pm

1 stop9h 33m

$361

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 3/29

4:43 pm-11:10 am

1 stop18h 27m

George Town Owen Roberts Intl

Fri 4/3

12:30 pm-9:55 am

1 stop21h 25m

$361

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 1/15

8:45 pm-12:25 pm

1 stop14h 40m

George Town Owen Roberts Intl

Mon 1/19

1:30 pm-10:05 pm

1 stop9h 35m

$361

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/10

4:38 pm-1:53 pm

3 stops20h 15m

George Town Owen Roberts Intl

Sat 1/17

2:34 pm-9:12 am

2 stops19h 38m

$364

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 3/21

8:40 pm-11:25 am

1 stop14h 45m

George Town Owen Roberts Intl

Fri 3/27

12:30 pm-9:50 am

1 stop21h 20m

$391

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 1/15

8:19 pm-11:35 am

1 stop14h 16m

George Town Owen Roberts Intl

Thu 1/22

2:50 pm-10:10 am

1 stop20h 20m

$405

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 1/8

4:10 pm-12:55 pm

2 stops19h 45m

George Town Owen Roberts Intl

Mon 1/12

1:50 pm-9:00 pm

1 stop8h 10m

$411

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 1/16

8:04 pm-2:50 pm

2 stops17h 46m

George Town Owen Roberts Intl

Mon 1/19

2:50 pm-10:10 am

1 stop20h 20m

$433

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 1/16

8:04 pm-2:50 pm

2 stops17h 46m

George Town Owen Roberts Intl

Thu 1/22

2:50 pm-10:10 am

1 stop20h 20m

$433

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 2/1

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Fri 2/6

2:50 pm-6:04 pm

Nonstop4h 14m

$438

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 31 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, December is the cheapest month in which you can book a flight from Chicago to Cayman Islands (average of $339). Flying from Chicago to Cayman Islands in September is currently the most expensive (average of $650). 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 December 18, 2025.

When flying from Chicago to Cayman Islands, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 40% versus a flight in the morning.

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 December 18, 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
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,005 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,091 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,054 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 19h 15m. Air Canada provides one of the quickest options available for as low as $361. 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 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 $513 for a flight from Chicago to Cayman Islands. The cheapest flight overall is $288 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $247.

  • 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, December is the cheapest month in which you can book a flight from Chicago to Cayman Islands (average of $339). Flying from Chicago to Cayman Islands in September is currently the most expensive (average of $650). 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 2 airlines flying from Chicago to Cayman Islands

Discover the top 2 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$341Average$680FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$452Average$724FlexibilityNo cancel feeOn-time71%

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