Cheap flights from Chicago (CHI) to the Cayman Islands

CHI — GCM
Feb 13 — Feb 201

How far in advance should I book a flight from Chicago to Cayman Islands?

Find a great deal and save up to 48% by booking at least 40 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Cayman Islands within the next two weeks, with the cheapest ticket starting at $788.

What is the cheapest month to fly from Chicago to Cayman Islands?

April is one of the best times of the year to fly to Cayman Islands from Chicago. Prices for April average $653 per person but you can even find prices for as low as $474. The most expensive prices can be found in the month of November. Opting for a April flight can save you 25% on your journey compared to booking in November

When is the cheapest time to fly from Chicago to Cayman Islands (CHI - KY)?

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.

Cheap flights from Chicago to Cayman Islands in February, March 2023

The best prices found for CHI to Cayman Islands flights for February, March

Chicago to Cayman Islands 2023 flight deals

Cheap flights to Cayman Islands from Chicago found for this year

Cheap Southwest flights from Chicago to Cayman Islands

Cheap Delta flights from Chicago to Cayman Islands

Non-stop flights to Cayman Islands from Chicago

Save time with Chicago to Cayman Islands direct flight deals

Last minute flights from Chicago to Cayman Islands

Late deals on return flights to Cayman Islands from Chicago, departing today and this week

One-way flights to Cayman Islands from Chicago

The cheapest one-way flights from Chicago to Cayman Islands

Reviews of Airlines Servicing Cayman Islands

Delta
7.9
Good
2,079 reviews

Entertainment

7.8

Food

7.2

Overall

7.9

Boarding

8.0

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Great flight. Able to watch end of one of the football games. Crew was very cheery. Despite the snowy weather in Chicago, the flight was relatively smooth and only slightly late. Great landing under the conditions. Glad to be home.

Delta
7.9
Good
2,079 reviews
Delta
7.9
Good
2,079 reviews

Entertainment

7.8

Food

7.2

Overall

7.9

Boarding

8.0

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Great flight. Able to watch end of one of the football games. Crew was very cheery. Despite the snowy weather in Chicago, the flight was relatively smooth and only slightly late. Great landing under the conditions. Glad to be home.

United Airlines
7.6
Good
1,218 reviews
Delta
7.9
Good
2,079 reviews

Entertainment

7.8

Food

7.2

Overall

7.9

Boarding

8.0

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Great flight. Able to watch end of one of the football games. Crew was very cheery. Despite the snowy weather in Chicago, the flight was relatively smooth and only slightly late. Great landing under the conditions. Glad to be home.

Southwest
7.5
Good
961 reviews
Delta
7.9
Good
2,079 reviews

Entertainment

7.8

Food

7.2

Overall

7.9

Boarding

8.0

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Great flight. Able to watch end of one of the football games. Crew was very cheery. Despite the snowy weather in Chicago, the flight was relatively smooth and only slightly late. Great landing under the conditions. Glad to be home.

Air Canada
6.6
Okay
671 reviews
Delta
7.9
Good
2,079 reviews

Entertainment

7.8

Food

7.2

Overall

7.9

Boarding

8.0

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Great flight. Able to watch end of one of the football games. Crew was very cheery. Despite the snowy weather in Chicago, the flight was relatively smooth and only slightly late. Great landing under the conditions. Glad to be home.

Related info for your journey

Useful info, stats and facts about Chicago to Cayman Islands flights.

Which airlines flying from Chicago to Cayman Islands have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Chicago to Cayman Islands that may be offering flexible cancellation policies are American Airlines, United Airlines, and Delta. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Can I find flights from Chicago to Cayman Islands for under $500 on Cheapflights?

Yes, there are multiple flights from Chicago to Cayman Islands for under $500. The cheapest flight booked recently is on Multiple Airlines for just $407, but on average you can expect to pay $447.

Are there nonstop flights from Chicago to Cayman Islands for under $600 on Cheapflights?

Cheapflights has at least 16 direct flights from Chicago to Cayman Islands under $600. A good price for a nonstop flight from Chicago to Cayman Islands is less than $1,280.

Are there last-minute flights available from Chicago to Cayman Islands for under $600?

There are currently 20+ open flights from Chicago to Cayman Islands within the next 7 days for less than $600.

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

The cheapest airline one-way is Air Canada, with whom users have recently found tickets for as low as $250. However, be on the lookout for offers from United Airlines 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 most popular airlines that fly from Chicago to Cayman Islands?

The most popular airlines flying from Chicago to Cayman Islands are Undisclosed Carrier, American Airlines and Alaska Airlines. Something to consider prior to booking your flight.

What are the cheapest flights from Chicago to Cayman Islands?

On average you can expect to pay $577 for a flight from Chicago to Cayman Islands. The cheapest flight overall is $261 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $393.

Top 5 airlines flying from Chicago to Cayman Islands

The chart below displays the airlines Cheapflights users traveling from Chicago to Cayman Islands choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$14Average$16FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
American AirlinesCheapest$235Average$637FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
United AirlinesCheapest$260Average$648FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
DeltaCheapest$556Average$651FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
Linear Air TaxiCheapest$8,547Average$51,983FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Linear Air Taxi flights
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