Cheap flights from Chicago Midway Airport to Caribbean from $98
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 Midway Airport to Caribbean departing on 7/12. 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 Midway Airport to Caribbean
Our best Frontier deals on Chicago Midway Airport to Caribbean flight tickets
Delta flights from Chicago Midway Airport to Caribbean
Our best Delta deals on Chicago Midway Airport to Caribbean flight tickets
How to get the cheapest flight ticket from Chicago Midway 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
What is the cheapest month to fly to Caribbean?
In general, August is the cheapest month to fly from Chicago Midway Airport to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $307. If you don’t want to visit Caribbean in August, then you should wait until November to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $317.
What is the cheapest day to depart on your flight to Caribbean?
The cheapest day to depart from Chicago Midway Airport to Caribbean is on a Tuesday when prices can be found for as low as $59. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $453. 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 Midway Airport to Caribbean when you can find flight prices for as low as $324. 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 $453.
What is the cheapest Chicago Midway to Caribbean flight route?
Fly from Chicago Midway to Punta Cana for the best Chicago Midway - 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 Midway Airport when booking 2 weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $410 when searching 2 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Chicago Midway Airport for as low as $309 on momondo.
What cabin class options are available on Chicago Midway to Caribbean flights?
There are 1 cabin classes available to choose from on Chicago Midway 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 Midway to Caribbean?
Frontier, Southwest, and Delta are the most popular carriers operating from Chicago Midway to Caribbean
What airlines fly to Caribbean?
Southwest, Frontier and Delta are the top three most popular airlines that fly to Caribbean from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 66% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 5 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 Midway Airport to Caribbean on average per day?
1 flights are operational daily from Chicago Midway Airport to Caribbean as of June 2025. The most popular departure time for this route is 9:00AM, with 100% of flights per day taking off at noon.
How many flights depart from Chicago Midway Airport to Caribbean on average per week?
As of June 2025, 10 flights take off from Chicago Midway Airport and land in Caribbean each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.
Cheap Chicago Midway Airport to Caribbean flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Caribbean
When did momondo last update prices for flights from Chicago Midway Airport to Caribbean?
Prices for flights from Chicago Midway Airport to Caribbean refresh daily.
How many operators does momondo search for flights from Chicago Midway Airport to Caribbean?
As of June 2025, there are 5 operators available to choose from for flights from Chicago Midway Airport to Caribbean.
How old do you have to be to fly from Chicago Midway 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 Midway Airport to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The travel and health documents you'll need for your trip to Caribbean 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 Caribbean. 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 Midway Airport to Caribbean?
momondo data reveals that the most frequently booked plane model on the route from Chicago Midway Airport to Caribbean is Boeing 737-700 Passenger/BBJ1 (winglets), representing 26.63% of all bookings. The subsequent popular models are Airbus A320neo at 16.79%, Boeing 737 MAX 8 at 14.67%, and Airbus A321-100/200 at 12.25%.
Best airlines flying from Chicago Midway Airport to Caribbean
Compare and see reviews for airlines that fly from Chicago Midway Airport to Caribbean with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $133 | Free Cancellation | Rating 5.9 3,299 reviews | |||
| PriceFrom $149 | Free Cancellation | Rating 6.3 8,064 reviews | |||
| PriceFrom $299 | Free Cancellation | Rating 7.4 8,809 reviews | |||
| PriceFrom $325 | Free Cancellation | Rating 8.0 7,964 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?
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 allows you to filter the results for Chicago to Caribbean flights to just show those with 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?
Of course. momondo tracks the price of Chicago to Caribbean flights. All you need is a valid email address and we will do the rest; it is that quick and easy.