Cheap flights from Chicago to Caribbean from $93
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 Caribbean departing on 6/25. 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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Frontier flights from Chicago to Caribbean
Our best Frontier deals on Chicago to Caribbean flight tickets
Spirit Airlines flights from Chicago to Caribbean
Our best Spirit Airlines deals on Chicago to Caribbean flight tickets
How to get the cheapest flight ticket from Chicago 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
What is the cheapest month to fly to Caribbean?
In general, September is the cheapest month to fly from Chicago to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $303. If you don’t want to visit Caribbean in September, then you should wait until August to fly from Chicago, when ticket prices are also cheap, with an average price of $319.
What is the cheapest day to depart on your flight to Caribbean?
The cheapest day to depart from Chicago to Caribbean is on a Monday when prices can be found for as low as $386. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $444. 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 to Caribbean when you can find flight prices for as low as $300. 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 $434.
What is the cheapest Chicago to Caribbean flight route?
Fly from Chicago O'Hare Intl to Punta Cana for the best Chicago - 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 when booking 7 weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $373 when searching 7 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Chicago for as low as $300 on momondo.
What cabin class options are available on Chicago to Caribbean flights?
There are 4 cabin classes available to choose from on Chicago 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 to Caribbean?
Frontier, Spirit Airlines, and American Airlines are the most popular carriers operating from Chicago 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 according to our data. American Airlines is the first choice among our users, with 35% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 11 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 to Caribbean on average per day?
The number of flights available between Chicago and Caribbean is 16 per day as of June 2025. The most frequent departure time is 8:00AM, with 81% of daily flights leaving at noon.
How many flights depart from Chicago to Caribbean on average per week?
The number of flights available between Chicago and Caribbean is 115 per week as of June 2025. The most frequent departure day is Sat, with 17% of weekly flights leaving on this day.
Cheap Chicago to Caribbean flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Caribbean
When did momondo last update prices for flights from Chicago to Caribbean?
Prices for flights from Chicago to Caribbean refresh daily.
How many operators does momondo search for flights from Chicago to Caribbean?
There are 11 operators available for flights from Chicago to Caribbean as of June 2025.
How old do you have to be to fly from Chicago 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 to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The required travel and health documents for your Caribbean 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 Caribbean. 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 to Caribbean?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Caribbean is Boeing 737-800 (20.29% of total bookings). The next most popular plane models are Airbus A321neo (18.09%), Boeing 737-900 (16.54%), and Boeing 737 MAX 9 (15.21%).
Best airlines flying from Chicago to Caribbean
Compare and see reviews for airlines that fly from Chicago to Caribbean with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $106 | Free Cancellation | Rating 5.9 3,296 reviews | |||
| PriceFrom $140 | Free Cancellation | Rating 6.3 8,061 reviews | |||
| PriceFrom $193 | Free Cancellation | Rating 7.5 1,452 reviews | |||
| PriceFrom $202 | Free Cancellation | Rating 7.3 2,922 reviews | |||
| PriceFrom $216 | Free Cancellation | Rating 8.0 7,963 reviews | |||
| PriceFrom $226 | Free Cancellation | Rating 7.4 8,801 reviews | |||
| PriceFrom $240 | Free Cancellation | Rating 7.3 26 reviews | |||
| PriceFrom $335 | Free Cancellation | Rating 7.1 9,553 reviews | |||
| PriceFrom $338 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $354 | Free Cancellation | Rating 8.0 4,278 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Caribbean?
Finding the right flight to Caribbean from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Caribbean quick and easy, saving you time and money.
Can I find flights from Chicago to Caribbean with flexible booking policies on momondo?
All flight searches from Chicago to Caribbean on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Chicago to Caribbean?
momondo helps you find the best flight between Chicago and Caribbean by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Chicago to Caribbean right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Caribbean 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.