Cheap flights from Chicago Midway Airport to Caribbean Islands from $87
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 Islands departing on 4/9. 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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Cheap round-trip flights
These are some of the best round-trip flight deals from Chicago Midway Airport to Caribbean Islands 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 Midway Airport to Caribbean Islands.
Cheap last minute flights
Planning a quick getaway from Chicago Midway Airport to Caribbean Islands? 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 Islands, so you can enjoy a seamless trip without layovers.
Southwest flights from Chicago Midway Airport to Caribbean Islands
Our best Southwest deals on Chicago Midway Airport to Caribbean Islands flight tickets
Southwest![Southwest]()
Apr 26![Southwest]()
Apr 29
MDW8:35 amChicago Midway
4h 40m
SJU2:15 pmSan Juan Luis Munoz Marin Intl
SJU8:00 amSan Juan Luis Munoz Marin Intl
11h 25m
1 stop
MDW6:25 pmChicago Midway
Southwest![Southwest]()
Sep 5![Southwest]()
Sep 9
MDW6:05 amChicago Midway
8h 05m
1 stop
SJU3:10 pmSan Juan Luis Munoz Marin Intl
SJU7:20 amSan Juan Luis Munoz Marin Intl
12h 50m
2 stops
MDW7:10 pmChicago Midway
Frontier flights from Chicago Midway Airport to Caribbean Islands
Our best Frontier deals on Chicago Midway Airport to Caribbean Islands flight tickets
Frontier![Frontier]()
Apr 1![Frontier]()
Apr 8
MDW4:40 pmChicago Midway
14h 53m
1 stop
SJU8:33 amSan Juan Luis Munoz Marin Intl
SJU2:12 pmSan Juan Luis Munoz Marin Intl
30h 23m
1 stop
MDW7:35 pmChicago Midway
Frontier![Frontier]()
Apr 1![Frontier]()
Apr 8
MDW4:40 pmChicago Midway
8h 10m
1 stop
SJU1:50 amSan Juan Luis Munoz Marin Intl
SJU2:55 amSan Juan Luis Munoz Marin Intl
17h 40m
1 stop
MDW7:35 pmChicago Midway
See travel insights to Caribbean Islands from
How to get the cheapest flight ticket from Chicago Midway Airport to Caribbean 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
Prices
Airlines
Other information
What is the cheapest month to fly to Caribbean Islands?
The month of May is, on average, the cheapest month to fly to Caribbean Islands from Chicago Midway Airport, with most prices found around $258. The month of September is another great option to travel to Caribbean Islands, with average flight prices from Chicago Midway Airport averaging around $304.
What is the cheapest day to depart on your flight to Caribbean Islands?
The cheapest day to depart from Chicago Midway Airport to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets 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 Islands.
What is the cheapest time of day to depart on your flight to Caribbean Islands?
According to our data, the cheapest time of day to fly to Caribbean Islands is in the evening. momondo users have found flights departing from Chicago Midway Airport to Caribbean Islands in the evening for as low as $324. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the morning because they tend to be around $456. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Chicago Midway to Caribbean Islands flight route?
Fly from Chicago Midway to Punta Cana for the best Chicago Midway - Caribbean Islands flight prices
How far in advance should I book a flight to Caribbean Islands?
You are more likely to see cheaper flights to Caribbean Islands from Chicago Midway Airport when booking 6 weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $396 when searching 6 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Chicago Midway Airport for as low as $287 on momondo.
What cabin class options are available on Chicago Midway to Caribbean Islands flights?
There are 1 cabin classes available to choose from on Chicago Midway to Caribbean 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 Midway to Caribbean Islands?
Frontier, Delta, and Southwest are the most popular carriers operating from Chicago Midway to Caribbean Islands
What airlines fly to Caribbean Islands?
Southwest, Delta and Frontier are the top three most popular airlines that fly to Caribbean Islands from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 52% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 4 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago Midway Airport to Caribbean Islands on average per day?
The number of flights available between Chicago Midway Airport and Caribbean Islands is 1 per day as of March 2025. The most frequent departure time is 9:00AM, with 100% of daily flights leaving at noon.
How many flights depart from Chicago Midway Airport to Caribbean Islands on average per week?
As of March 2025, 7 flights take off from Chicago Midway Airport and land in Caribbean Islands each week. The most common flight departure day for this route is Tue, with 29% of weekly flights taking off on this day.
Cheap Chicago Midway Airport to Caribbean Islands flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Caribbean Islands
Best Price Found | $87 |
|---|---|
Fastest flight time | 4h 00m |
Direct flights | Every day |
Airports in Caribbean Islands | 5 airports |
When did momondo last update prices for flights from Chicago Midway Airport to Caribbean Islands?
Prices for flights from Chicago Midway Airport to Caribbean Islands were last updated today.
How many operators does momondo search for flights from Chicago Midway Airport to Caribbean Islands?
There are 4 operators available for flights from Chicago Midway Airport to Caribbean Islands as of March 2025.
How old do you have to be to fly from Chicago Midway Airport to Caribbean Islands?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The necessary travel and health documents for your Caribbean Islands 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 Chicago Midway Airport to Caribbean Islands?
momondo data reveals that the most frequently booked plane model on the route from Chicago Midway Airport to Caribbean Islands is Airbus A320neo, representing 16.80% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 13.79%, Airbus A321neo at 11.78%, and Boeing 737-800 at 10.71%.
Best airlines flying from Chicago Midway Airport to Caribbean Islands
Compare and see reviews for airlines that fly from Chicago Midway Airport to Caribbean Islands with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $133 | Free Cancellation | Rating 6.0 3,292 reviews | |||
| PriceFrom $174 | Free Cancellation | Rating 6.3 7,896 reviews | |||
| PriceFrom $325 | Free Cancellation | Rating 8.0 7,944 reviews | |||
| PriceFrom $337 | Free Cancellation | Rating 8.0 4,292 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Caribbean Islands?
Finding the right flight to Caribbean Islands 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 Islands quick and easy, saving you time and money.
Can I find flights from Chicago to Caribbean Islands with flexible booking policies on momondo?
Yes. All flights to Caribbean 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 Caribbean Islands?
momondo provides multiple filters to help you find the best flight to Caribbean Islands from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Chicago to Caribbean Islands right now. Can momondo alert me if prices change?
Price alerts on flights to Caribbean Islands from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.
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