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