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Cayman Islands

$113+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$310
(Priceline)

One-way from

$113
(Expedia)

Popular in

December

Cheapest in

October

Average price

$539

Good round-trip deal

$454 or less

Good one-way deal

$582 or less
Provider with most accurate pricing for Chicago (CHI)-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-George Town Owen Roberts Intl flights.
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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. 10% potential increase in price ($78 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 October 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 October 30, 2025.

This Priceline deal was found by Cheapflights users on 10/29. 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 12/67:10 amORD - GCM
1 stop8h 45mSpirit Airlines
Sat 12/135:56 pmGCM - ORD
1 stop7h 13mSpirit Airlines
Deal found 10/29$310
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 11/298:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Sat 12/62:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 10/28$338
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Fri 12/126:45 amORD - GCM
1 stop6h 21mAmerican Airlines
Fri 12/193:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 10/30$342
This American Airlines deal was found by Cheapflights users on 10/30. 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 12/145:00 amORD - GCM
1 stop6h 00mAmerican Airlines
Sun 12/213:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 10/30$347
This United Airlines deal was found by Cheapflights users on 10/30. 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 12/318:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Wed 1/72:25 pmGCM - ORD
1 stop9h 34mUnited Airlines
Deal found 10/30$350
This Delta deal was found by Cheapflights users on 10/28. 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 12/77:53 pmORD - GCM
1 stop15h 42mDelta
Fri 12/121:50 pmGCM - ORD
1 stop11h 11mDelta
Deal found 10/28$352
This Delta deal was found by Cheapflights users on 10/28. 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 12/76:00 amMDW - GCM
1 stop5h 35mDelta
Wed 12/171:50 pmGCM - MDW
1 stop10h 57mDelta
Deal found 10/28$352
This American Airlines deal was found by Cheapflights users on 10/28. 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 10/28$363
This Delta deal was found by Cheapflights users on 10/28. 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 12/86:00 amMDW - GCM
1 stop5h 35mDelta
Fri 12/121:50 pmGCM - MDW
1 stop10h 57mDelta
Deal found 10/28$385
This Delta deal was found by Cheapflights users on 10/28. 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.
Sat 12/66:00 amMDW - GCM
1 stop5h 30mDelta
Wed 12/171:50 pmGCM - MDW
1 stop10h 57mDelta
Deal found 10/28$443
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/62:59 pmMDW - GCM
1 stop19h 36mMultiple Airlines
Sat 12/138:50 amGCM - MDW
1 stop14h 40mMultiple Airlines
Deal found 10/28$473
This Delta deal was found by Cheapflights users on 10/28. 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.
Sat 12/66:00 amMDW - GCM
1 stop5h 30mDelta
Fri 12/121:50 pmGCM - MDW
1 stop10h 57mDelta
Deal found 10/28$476

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 October 30, 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

Fri 2/6

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Fri 2/13

2:50 pm-6:04 pm

Nonstop4h 14m

$342

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 1/15

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Sun 1/18

2:50 pm-6:04 pm

Nonstop4h 14m

$342

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/24

8:52 am-4:35 pm

1 stop6h 43m

George Town Owen Roberts Intl

Sun 2/1

2:50 pm-6:04 pm

Nonstop4h 14m

$346

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 11/29

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Sat 12/6

5:45 pm-12:15 am

1 stop7h 30m

$348

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/31

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Wed 1/7

2:25 pm-10:59 pm

1 stop9h 34m

$350

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/24

5:30 am-12:36 pm

1 stop6h 06m

George Town Owen Roberts Intl

Wed 12/31

1:52 pm-7:38 pm

1 stop6h 46m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 12/25

5:30 am-2:27 pm

1 stop7h 57m

George Town Owen Roberts Intl

Wed 12/31

1:52 pm-7:38 pm

1 stop6h 46m

$352

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 12/11

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Mon 12/15

1:50 pm-11:47 pm

1 stop10h 57m

$352

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 12/24

6:00 am-12:36 pm

1 stop5h 36m

George Town Owen Roberts Intl

Wed 12/31

1:52 pm-10:22 pm

1 stop9h 30m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 2/21

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Sat 2/28

5:45 pm-12:26 am

1 stop7h 41m

$352

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 39 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 $381). 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 October 30, 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 41% 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 October 30, 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
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

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
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

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
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

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
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

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 4h. United Airlines provides one of the quickest options available for as low as $342. 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 Southwest, with whom users have recently found tickets for as low as $126. However, be on the lookout for offers from Air Canada and Delta, 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 $644 for a flight from Chicago to Cayman Islands. The cheapest flight overall is $341 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $338.

  • 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 $381). 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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Midway to Castries flights
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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$434Average$722FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$504Average$711FlexibilityNo cancel feeOn-time71%
DeltaCheapest$564Average$798FlexibilityNo cancel feeOn-timeN/A

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