Cheap flights from Chicago O'Hare Intl Airport to Caribbean from $82
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 Caribbean departing on 5/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Round-trip
1 adult
Economy
0 bags
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One-way
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Cheap round-trip flights
These are some of the best round-trip flight deals from Chicago O'Hare Intl Airport 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 Chicago O'Hare Intl Airport to Caribbean.
Cheap last minute flights
Planning a quick getaway from Chicago O'Hare Intl Airport 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.
Spirit Airlines flights from Chicago O'Hare Intl Airport to Caribbean
Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to Caribbean flight tickets
Spirit Airlines![Spirit Airlines]()
May 19![Spirit Airlines]()
May 29
ORD11:30 amChicago O'Hare Intl
4h 46m
SJU5:16 pmSan Juan Luis Munoz Marin Intl
SJU8:12 pmSan Juan Luis Munoz Marin Intl
13h 38m
1 stop
ORD8:50 amChicago O'Hare Intl
Spirit Airlines![Spirit Airlines]()
May 25![Spirit Airlines]()
Jun 2
ORD8:17 amChicago O'Hare Intl
10h 45m
1 stop
SJU8:02 pmSan Juan Luis Munoz Marin Intl
SJU8:12 pmSan Juan Luis Munoz Marin Intl
13h 38m
1 stop
ORD8:50 amChicago O'Hare Intl
United Airlines flights from Chicago O'Hare Intl Airport to Caribbean
Our best United Airlines deals on Chicago O'Hare Intl Airport to Caribbean flight tickets
United Airlines![United Airlines]()
May 12![United Airlines]()
May 15
ORD9:23 amChicago O'Hare Intl
4h 42m
PUJ3:05 pmPunta Cana
PUJ1:50 pmPunta Cana
5h 05m
ORD5:55 pmChicago O'Hare Intl
United Airlines![United Airlines]()
May 11![United Airlines]()
May 23
ORD9:23 amChicago O'Hare Intl
4h 42m
PUJ3:05 pmPunta Cana
PUJ1:50 pmPunta Cana
5h 05m
ORD5:55 pmChicago O'Hare Intl
How to get the cheapest flight ticket from Chicago O'Hare Intl Airport 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 Chicago O'Hare Intl Airport to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $289. If you don’t want to visit Caribbean in August, then you should wait until May to fly from Chicago O'Hare Intl Airport, when ticket prices are also cheap, with an average price of $328.
What is the cheapest day to depart on your flight to Caribbean?
The cheapest day to depart from Chicago O'Hare Intl Airport to Caribbean is on a Tuesday when prices can be found for as low as $365. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $421. 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 evening is the cheapest time of day to fly from Chicago O'Hare Intl Airport to Caribbean when you can find flight prices for as low as $298. Flying to Caribbean in the evening 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 $409.
What is the cheapest Chicago O'Hare Intl to Caribbean flight route?
Fly from Chicago O'Hare Intl to Punta Cana for the best Chicago O'Hare Intl - Caribbean flight prices
How far in advance should I book a flight to Caribbean?
You are more likely to see cheaper flights to Caribbean from Chicago O'Hare Intl Airport when booking 5 weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $367 when searching 5 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Chicago O'Hare Intl Airport for as low as $293 on momondo.
What cabin class options are available on Chicago O'Hare Intl to Caribbean flights?
There are 4 cabin classes available to choose from on Chicago O'Hare Intl 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 Chicago O'Hare Intl to Caribbean?
Spirit Airlines, Frontier, and United Airlines are the most popular carriers operating from Chicago O'Hare Intl 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 Chicago O'Hare Intl Airport according to our data. American Airlines is the first choice among our users, with 36% 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 Chicago O'Hare Intl Airport to Caribbean on average per day?
As of May 2025, 11 flights take off from Chicago O'Hare Intl Airport and land in Caribbean each day. The most common flight departure time for this route is 8:00AM, with 80% of daily flights taking off at noon.
How many flights depart from Chicago O'Hare Intl Airport to Caribbean on average per week?
The number of flights available between Chicago O'Hare Intl Airport and Caribbean is 78 per week as of May 2025. The most frequent departure day is Thu, with 18% of weekly flights leaving on this day.
Cheap Chicago O'Hare Intl Airport to Caribbean flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Caribbean
When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Caribbean?
Prices for flights from Chicago O'Hare Intl Airport to Caribbean refresh daily.
How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Caribbean?
As of May 2025, there are 10 operators available to choose from for flights from Chicago O'Hare Intl Airport to Caribbean.
How old do you have to be to fly from Chicago O'Hare Intl Airport to Caribbean?
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 O'Hare Intl Airport to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The travel and health documents required for your trip to Caribbean can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago O'Hare Intl Airport to Caribbean?
momondo data reveals that the most frequently booked plane model on the route from Chicago O'Hare Intl Airport to Caribbean is Boeing 737-800, representing 19.88% of all bookings. The subsequent popular models are Boeing 737 MAX 9 at 18.67%, Boeing 737-900 at 18.48%, and Airbus A320neo at 18.02%.
Best airlines flying from Chicago O'Hare Intl Airport to Caribbean
Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Caribbean with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $124 | Free Cancellation | Rating 5.9 3,287 reviews | |||
| PriceFrom $142 | Free Cancellation | Rating 6.3 7,963 reviews | |||
| PriceFrom $193 | Free Cancellation | Rating 7.5 1,415 reviews | |||
| PriceFrom $216 | Free Cancellation | Rating 8.0 7,934 reviews | |||
| PriceFrom $226 | Free Cancellation | Rating 7.4 8,696 reviews | |||
| PriceFrom $293 | Free Cancellation | Rating 7.3 2,923 reviews | |||
| PriceFrom $335 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $335 | Free Cancellation | Rating 7.0 9,252 reviews | |||
| PriceFrom $385 | Free Cancellation | Rating 8.0 4,294 reviews | |||
| PriceFrom $397 | Free Cancellation | Rating 6.7 2,317 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Caribbean?
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 Caribbean for you.
Can I find flights from Chicago to Caribbean with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Caribbean from Chicago with this policy.
How can momondo help me find flights from Chicago to Caribbean?
Once all potential Chicago to Caribbean 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 Chicago to Caribbean right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Caribbean, momondo offers a useful price alert feature which will track prices for flights to Caribbean from Chicago and alert you when they change.
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