Cheap flights from Illinois to Caribbean from $60
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 Caribbean departing on 1/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Round-trip
1 adult
Economy
0 bags
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Cheap round-trip flights
These are some of the best round-trip flight deals from Illinois to Caribbean that have been recently found on momondo from popular airlines, departing in the coming months.
Cheap one-way flights
Flying one-way? These are some of the best deals recently discovered on momondo for flights from Illinois to Caribbean.
Cheap last minute flights
Planning a quick getaway from Illinois to Caribbean? These are the last-minute flight deals available now.
Cheap direct flights
If you prefer a non-stop journey, check out our latest direct flight deals to Caribbean, so you can enjoy a seamless trip without layovers.
Cheap bus & train deals from Illinois to Caribbean
Find recent round-trip train or bus tickets from Illinois to Caribbean.
All round-trip flight deals to Caribbean
The cheapest plane tickets to Caribbean found on KAYAK recently.
Frontier flights from Illinois to Caribbean
Our best Frontier deals on Illinois to Caribbean flight tickets
Frontier![Frontier]()
Mar 3![Frontier]()
Mar 4
ORD7:08 pmChicago O'Hare Intl
12h 41m
1 stop
SJU9:49 amSan Juan Luis Munoz Marin Intl
SJU9:30 pmSan Juan Luis Munoz Marin Intl
13h 57m
1 stop
ORD9:27 amChicago O'Hare Intl
Frontier![Frontier]()
Feb 22![Frontier]()
Feb 25
ORD8:44 pmChicago O'Hare Intl
10h 51m
1 stop
SJU9:35 amSan Juan Luis Munoz Marin Intl
SJU9:30 pmSan Juan Luis Munoz Marin Intl
13h 57m
1 stop
ORD9:27 amChicago O'Hare Intl
Spirit Airlines flights from Illinois to Caribbean
Our best Spirit Airlines deals on Illinois to Caribbean flight tickets
Spirit Airlines![Spirit Airlines]()
Feb 25![Spirit Airlines]()
Feb 28
ORD12:21 pmChicago O'Hare Intl
4h 31m
SJU6:52 pmSan Juan Luis Munoz Marin Intl
SJU8:31 pmSan Juan Luis Munoz Marin Intl
5h 24m
ORD11:55 pmChicago O'Hare Intl
Spirit Airlines![Spirit Airlines]()
Jan 27![Spirit Airlines]()
Feb 6
ORD1:44 pmChicago O'Hare Intl
4h 37m
SJU8:21 pmSan Juan Luis Munoz Marin Intl
SJU10:09 pmSan Juan Luis Munoz Marin Intl
14h 08m
1 stop
ORD10:17 amChicago O'Hare Intl
How to get the cheapest flight ticket from Illinois to Caribbean
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
Prices
Airlines
Other information
What is the cheapest month to fly to Caribbean?
In general, August is the cheapest month to fly from Illinois to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $290. If you don’t want to visit Caribbean in August, then you should wait until September to fly from Illinois, when ticket prices are also cheap, with an average price of $290.
What is the cheapest day to depart on your flight to Caribbean?
The cheapest day to depart from Illinois to Caribbean is on a Tuesday when prices can be found for as low as $352. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $413. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean.
What is the cheapest time of day to depart on your flight to Caribbean?
In the afternoon is the cheapest time of day to fly from Illinois to Caribbean when you can find flight prices for as low as $306. Flying to Caribbean in the afternoon is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $389.
What is the cheapest Illinois to Caribbean flight route?
Fly from Chicago O'Hare Intl to Punta Cana for the best Illinois - Caribbean flight prices
How far in advance should I book a flight to Caribbean?
The ideal time to book your flight to Caribbean is 49 days in advance when prices tend to average $364. Keep in mind that you might also find cheap flights to Caribbean outside of this time window. In fact, momondo users recently found flights from Illinois to Caribbean for $259.
What cabin class options are available on Illinois to Caribbean flights?
There are 4 cabin classes available to choose from on Illinois to Caribbean 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 Caribbean?
Frontier, Spirit Airlines, and Southwest are the most popular carriers operating from Illinois to Caribbean
What airlines fly to Caribbean?
American Airlines, Spirit Airlines and United Airlines are the top three most popular airlines that fly to Caribbean from Illinois according to our data. American Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 10 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.
How many flights depart from Illinois to Caribbean on average per day?
9 flights are operational daily from Illinois to Caribbean as of January 2025. The most popular departure time for this route is 8:00AM, with 83% of flights per day taking off at noon.
How many flights depart from Illinois to Caribbean on average per week?
66 flights are operational weekly from Illinois to Caribbean as of January 2025. The most popular departure day for this route is Mon, with 18% of flights per week taking off on this day.
Cheap Illinois to Caribbean flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Illinois to Caribbean
When did momondo last update prices for flights from Illinois to Caribbean?
Prices for flights from Illinois to Caribbean were last updated today.
How many operators does momondo search for flights from Illinois to Caribbean?
There are 10 operators available for flights from Illinois to Caribbean as of January 2025.
How old do you have to be to fly from Illinois to Caribbean?
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 Caribbean.
What documentation or ID do you need to fly to Caribbean?
The necessary travel and health documents for your Caribbean trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Illinois to Caribbean?
Based on momondo bookings for flights between Illinois and Caribbean, the leading plane model is Boeing 737-800, making up 26.64% of the total bookings. Other popular models include Boeing 737 MAX 9 with 22.65%, Airbus A320neo with 14.15%, and Boeing 737-900 with 13.08%.
Best airlines flying from Illinois to Caribbean
Compare and see reviews for airlines that fly from Illinois to Caribbean with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $65 | Free Cancellation | Rating 6.0 3,431 reviews | |||
| PriceFrom $156 | Free Cancellation | Rating 6.3 8,089 reviews | |||
| PriceFrom $173 | Free Cancellation | Rating 7.4 3,196 reviews | |||
| PriceFrom $194 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $226 | Free Cancellation | Rating 7.6 1,657 reviews | |||
| PriceFrom $256 | Free Cancellation | Rating 7.4 8,961 reviews | |||
| PriceFrom $317 | Free Cancellation | Rating 8.1 4,659 reviews | |||
| PriceFrom $324 | Free Cancellation | Rating 8.0 8,508 reviews | |||
| PriceFrom $335 | Free Cancellation | Rating 7.0 8,571 reviews | |||
| PriceFrom $1,422 | Free Cancellation | Rating 6.9 2,571 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Illinois to Caribbean?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Illinois to Caribbean. momondo saves you time and could save you money on your trip.
Can I find flights from Illinois to Caribbean with flexible booking policies on momondo?
momondo does allow users to show only those flights to Caribbean from Illinois which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Illinois to Caribbean?
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 Illinois to Caribbean.
I’m not ready to book a flight from Illinois to Caribbean right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Illinois to Caribbean flights. All you need is a valid email address and we will do the rest; it is that quick and easy.
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Find better results for your trip to Caribbean
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