Cheap flights from Chicago O'Hare Intl Airport to the Cayman Islands from $181
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago O'Hare Intl Airport to the Cayman Islands departing on 6/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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American Airlines flights from Chicago O'Hare Intl Airport to Cayman Islands
Our best American Airlines deals on Chicago O'Hare Intl Airport to Cayman Islands flight tickets
Air Canada flights from Chicago O'Hare Intl Airport to Cayman Islands
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How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Cayman Islands
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Cayman Islands?
If you aren’t able to travel to Cayman Islands during the month of September, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $575.
What is the cheapest day to depart on your flight to Cayman Islands?
Our data shows that Sunday is the least expensive day to fly to Cayman Islands. Tickets to fly out on this day can be as low as $688. Be sure to avoid booking your departure on a Friday as prices are generally higher than usual. According to our data, the average ticket price to Cayman Islands on Friday is $1,039.
What is the cheapest time of day to depart on your flight to Cayman Islands?
According to our data, the cheapest time of day to fly to Cayman Islands is in the afternoon. momondo users have found flights departing from Chicago O'Hare Intl Airport to Cayman Islands in the afternoon for as low as $507. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $713 on average. Flights to Cayman Islands from Chicago O'Hare Intl Airport in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.
What is the cheapest Chicago O'Hare Intl to Cayman Islands flight route?
Fly from Chicago O'Hare Intl to George Town Owen Roberts Intl for the best Chicago O'Hare Intl - Cayman Islands flight prices
How far in advance should I book a flight to Cayman Islands?
You are more likely to see cheaper flights to Cayman Islands from Chicago O'Hare Intl Airport when booking 23 weeks ahead of your departure date. In general, you can expect to find flights to Cayman Islands for around $668 when searching 23 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Cayman Islands from Chicago O'Hare Intl Airport for as low as $623 on momondo.
What cabin class options are available on Chicago O'Hare Intl to Cayman Islands flights?
There are 3 cabin classes available to choose from on Chicago O'Hare Intl to Cayman Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Chicago O'Hare Intl to Cayman Islands?
Air Canada, Southwest, and American Airlines are the most popular carriers operating from Chicago O'Hare Intl to Cayman Islands
What airlines fly to Cayman Islands?
American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Cayman Islands from Chicago O'Hare Intl Airport according to our data. American Airlines is the first choice among our users, with 47% of people opting to fly with this airline when traveling to Cayman Islands. Keep in mind that there are 3 different airlines that fly to Cayman Islands on a routine basis, so you have a few additional options to choose from.
Cheap Chicago O'Hare Intl Airport to Cayman Islands flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Cayman Islands
When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Cayman Islands?
Prices for flights from Chicago O'Hare Intl Airport to Cayman Islands refresh daily.
How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Cayman Islands?
As of April 2025, there are 3 operators available to choose from for flights from Chicago O'Hare Intl Airport to Cayman Islands.
How old do you have to be to fly from Chicago O'Hare Intl Airport to Cayman Islands?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Cayman Islands.
What documentation or ID do you need to fly to Cayman Islands?
The required travel and health documents for your Cayman Islands trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Cayman Islands. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Chicago O'Hare Intl Airport to Cayman Islands?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago O'Hare Intl Airport to Cayman Islands is Boeing 737-800 (72.58% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (11.29%), Boeing 737 MAX 9 (6.45%), and Boeing 737-900 (6.45%).
Best airlines flying from Chicago O'Hare Intl Airport to Cayman Islands
Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Cayman Islands with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $463 | Free Cancellation | Rating 8.0 7,917 reviews | |||
| PriceFrom $468 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $503 | Free Cancellation | Rating 7.4 8,667 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Cayman Islands?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Cayman Islands for you.
Can I find flights from Chicago to Cayman Islands with flexible booking policies on momondo?
Yes. All flights to Cayman Islands from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Chicago to Cayman Islands?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Cayman Islands.
I’m not ready to book a flight from Chicago to Cayman Islands right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Chicago to Cayman Islands flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.