Cheap flights from Chicago (CHI) to the Cayman Islands
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 O'Hare Intl
George Town Owen Roberts Intl
1 stop
19h 43mGeorge Town Owen Roberts Intl
Chicago O'Hare Intl
1 stop
23h 52mMultiple Airlines
Chicago O'Hare Intl
George Town Owen Roberts Intl
1 stop
19h 43mGeorge Town Owen Roberts Intl
Chicago O'Hare Intl
1 stop
23h 52mMultiple Airlines
Chicago O'Hare Intl
George Town Owen Roberts Intl
1 stop
19h 43mGeorge Town Owen Roberts Intl
Chicago O'Hare Intl
2 stops
26h 54mMultiple Airlines
Chicago to Cayman Islands 2023 flight deals
Cheap flights to Cayman Islands from Chicago found for this year
Chicago O'Hare Intl
George Town Owen Roberts Intl
1 stop
19h 43mGeorge Town Owen Roberts Intl
Chicago O'Hare Intl
1 stop
23h 52mMultiple Airlines
Chicago O'Hare Intl
George Town Owen Roberts Intl
1 stop
19h 43mGeorge Town Owen Roberts Intl
Chicago O'Hare Intl
1 stop
23h 52mMultiple Airlines
Chicago O'Hare Intl
George Town Owen Roberts Intl
1 stop
19h 43mGeorge Town Owen Roberts Intl
Chicago O'Hare Intl
2 stops
26h 54mMultiple Airlines
Cheap Southwest flights from Chicago to Cayman Islands
Chicago O'Hare Intl
George Town Owen Roberts Intl
1 stop
21h 35mGeorge Town Owen Roberts Intl
Chicago O'Hare Intl
2 stops
19h 30mSouthwest
Chicago O'Hare Intl
George Town Owen Roberts Intl
2 stops
23h 45mGeorge Town Owen Roberts Intl
Chicago O'Hare Intl
2 stops
19h 30mSouthwest
Cheap Delta flights from Chicago to Cayman Islands
Chicago Midway
George Town Owen Roberts Intl
1 stop
5h 30mGeorge Town Owen Roberts Intl
Chicago Midway
1 stop
8h 55mDelta
Chicago Midway
George Town Owen Roberts Intl
1 stop
5h 30mGeorge Town Owen Roberts Intl
Chicago Midway
2 stops
20h 23mDelta
Chicago Midway
George Town Owen Roberts Intl
1 stop
5h 30mGeorge Town Owen Roberts Intl
Chicago Midway
1 stop
9h 12mDelta
Non-stop flights to Cayman Islands from Chicago
Save time with Chicago to Cayman Islands direct flight deals
Chicago O'Hare Intl
George Town Owen Roberts Intl
Nonstop
3h 59mGeorge Town Owen Roberts Intl
Chicago O'Hare Intl
Nonstop
4h 06mUnited Airlines
Chicago O'Hare Intl
George Town Owen Roberts Intl
Nonstop
4h 01mGeorge Town Owen Roberts Intl
Chicago O'Hare Intl
Nonstop
4h 15mUnited Airlines
Chicago O'Hare Intl
George Town Owen Roberts Intl
Nonstop
4h 01mGeorge Town Owen Roberts Intl
Chicago O'Hare Intl
Nonstop
4h 15mUnited Airlines
Last minute flights from Chicago to Cayman Islands
Late deals on return flights to Cayman Islands from Chicago, departing today and this week
Chicago Midway
George Town Owen Roberts Intl
1 stop
6h 23mGeorge Town Owen Roberts Intl
Chicago Midway
1 stop
23h 12mMultiple Airlines
Chicago Midway
George Town Owen Roberts Intl
1 stop
6h 23mGeorge Town Owen Roberts Intl
Chicago Midway
1 stop
13h 36mMultiple Airlines
Chicago Midway
George Town Owen Roberts Intl
1 stop
26h 55mGeorge Town Owen Roberts Intl
Chicago Midway
1 stop
13h 36mMultiple Airlines
One-way flights to Cayman Islands from Chicago
The cheapest one-way flights from Chicago to Cayman Islands
Chicago O'Hare Intl
George Town Owen Roberts Intl
1 stop
22h 10mMultiple Airlines
Chicago O'Hare Intl
George Town Owen Roberts Intl
2 stops
20h 40mMultiple Airlines
Chicago O'Hare Intl
George Town Owen Roberts Intl
2 stops
18h 13mMultiple Airlines
Reviews of Airlines Servicing Cayman Islands
Entertainment
Food
Overall
Boarding
Comfort
Crew
Reviews
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.
Entertainment
Food
Overall
Boarding
Comfort
Crew
Reviews
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.
Entertainment
Food
Overall
Boarding
Comfort
Crew
Reviews
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.
Entertainment
Food
Overall
Boarding
Comfort
Crew
Reviews
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.
Entertainment
Food
Overall
Boarding
Comfort
Crew
Reviews
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.