Cheap flights from Chicago to the Cayman Islands from $176
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 to the Cayman Islands departing on 7/1. 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 to Cayman Islands
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Delta flights from Chicago to Cayman Islands
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How to get the cheapest flight ticket from Chicago 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 $544.
What is the cheapest day to depart on your flight to Cayman Islands?
Our data shows that Tuesday is the least expensive day to fly to Cayman Islands. Tickets to fly out on this day can be as low as $701. 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 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 $723 on average. Flights to Cayman Islands from Chicago in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.
What is the cheapest Chicago to Cayman Islands flight route?
Fly from Chicago O'Hare Intl to George Town Owen Roberts Intl for the best Chicago - 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 when booking 14 weeks ahead of your departure date. In general, you can expect to find flights to Cayman Islands for around $680 when searching 14 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Cayman Islands from Chicago for as low as $618 on momondo.
What cabin class options are available on Chicago to Cayman Islands flights?
There are 3 cabin classes available to choose from on Chicago 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 to Cayman Islands?
Southwest, Air Canada, and American Airlines are the most popular carriers operating from Chicago 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 according to our data. American Airlines is the first choice among our users, with 48% 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 many flights depart from Chicago to Cayman Islands on average per week?
1 flights are operational weekly from Chicago to Cayman Islands as of June 2025. The most popular departure day for this route is Sat, with 100% of flights per week taking off on this day.
Cheap Chicago to Cayman Islands flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Cayman Islands
When did momondo last update prices for flights from Chicago to Cayman Islands?
Prices for flights from Chicago to Cayman Islands refresh daily.
How many operators does momondo search for flights from Chicago to Cayman Islands?
The number of operators available for flights from Chicago to Cayman Islands is 3 as of June 2025.
How old do you have to be to fly from Chicago to Cayman Islands?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago 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 Chicago to Cayman Islands?
Based on momondo bookings for flights between Chicago and Cayman Islands, the leading plane model is Boeing 737-800, making up 73.87% of the total bookings. Other popular models include Boeing 737 MAX 9 with 8.11%, Boeing 737-900 with 8.11%, and Boeing 737 MAX 8 with 4.50%.
Best airlines flying from Chicago to Cayman Islands
Compare and see reviews for airlines that fly from Chicago to Cayman Islands with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $463 | Free Cancellation | Rating 8.0 7,963 reviews | |||
| PriceFrom $474 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $522 | Free Cancellation | Rating 7.4 8,801 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Cayman Islands?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Cayman Islands. momondo saves you time and could save you money on your trip.
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?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Cayman Islands from Chicago.
I’m not ready to book a flight from Chicago to Cayman Islands right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Cayman Islands from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.