Cheap flights from Illinois 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 Illinois 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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Southwest flights from Illinois to Cayman Islands
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How to get the cheapest flight ticket from Illinois 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 November is also cheap. Prices for this month can be found on momondo for an average of $601.
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 Illinois 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 Illinois in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.
What is the cheapest Illinois to Cayman Islands flight route?
Fly from Chicago O'Hare Intl to George Town Owen Roberts Intl for the best Illinois - 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 Illinois 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 Illinois for as low as $623 on momondo.
What cabin class options are available on Illinois to Cayman Islands flights?
There are 3 cabin classes available to choose from on Illinois 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 Illinois to Cayman Islands?
Air Canada, Southwest, and American Airlines are the most popular carriers operating from Illinois 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 Illinois according to our data. American Airlines is the first choice among our users, with 50% 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.
How long is the flight from Illinois to Cayman Islands?
Flight times vary depending on what airport in Illinois you fly out of and what airport in Cayman Islands you fly into. For example, flying from Chicago to George Town takes 4h 36m on average. On the other hand, flying from Moline to George Town takes 19h 05m on average. Keep in mind that it’s always quicker to opt for a non-stop flight, so be sure to check momondo if there are any available for your route.
Cheap Illinois to Cayman Islands flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Illinois to Cayman Islands
When did momondo last update prices for flights from Illinois to Cayman Islands?
Prices for flights from Illinois to Cayman Islands were last updated today.
How many operators does momondo search for flights from Illinois to Cayman Islands?
As of April 2025, there are 4 operators available to choose from for flights from Illinois to Cayman Islands.
How old do you have to be to fly from Illinois 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 Illinois to Cayman Islands.
What documentation or ID do you need to fly to Cayman Islands?
The travel and health documents you'll need for your trip to Cayman Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Cayman Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Illinois to Cayman Islands?
momondo data reveals that the most frequently booked plane model on the route from Illinois to Cayman Islands is Boeing 737-800, representing 72.58% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 11.29%, Boeing 737 MAX 9 at 6.45%, and Boeing 737-900 at 6.45%.
Best airlines flying from Illinois to Cayman Islands
Compare and see reviews for airlines that fly from Illinois to Cayman Islands with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $446 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $463 | Free Cancellation | Rating 8.0 7,917 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 Illinois to Cayman Islands?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Illinois to Cayman Islands. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Illinois to Cayman Islands with flexible booking policies on momondo?
Yes. All flights to Cayman Islands from Illinois on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Illinois to Cayman Islands?
Once all potential Illinois to Cayman Islands flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Illinois to Cayman Islands right now. Can momondo alert me if prices change?
Price alerts on flights to Cayman Islands from Illinois are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.