Cheap flights from Caribbean to Chicago from $137
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Caribbean to Chicago departing on 6/3. 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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Southwest flights from Caribbean to Chicago Midway Airport
Our best Southwest deals on Caribbean to Chicago Midway Airport flight tickets
Delta flights from Caribbean to Chicago Midway Airport
Our best Delta deals on Caribbean to Chicago Midway Airport flight tickets
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How to get the cheapest flight ticket from Caribbean to Chicago Midway Airport
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 Chicago Midway Airport?
The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from Caribbean, with most prices found around $252. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Caribbean during the month August is also very affordable. Most momondo users find prices during this month for around $270.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Caribbean. The lowest ticket price found for a Friday departure recently was $154. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Saturday is the most expensive day to depart from Caribbean because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $610.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Caribbean in the evening is the least expensive time of day to depart. momondo users have found prices as low as $237 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $614. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Caribbean to Chicago Midway flight route?
Fly from San Juan Luis Munoz Marin Intl to Chicago Midway for the best Caribbean - Chicago Midway flight prices
How far in advance should I book a flight to Chicago Midway Airport?
You are more likely to see cheaper flights to Chicago Midway Airport from Caribbean when booking 6 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $365 when searching 6 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Caribbean for as low as $241 on momondo.
What cabin class options are available on Caribbean to Chicago Midway flights?
There are 1 cabin classes available to choose from on Caribbean to Chicago Midway 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 Caribbean to Chicago Midway?
Southwest, Frontier, and Delta are the most popular carriers operating from Caribbean to Chicago Midway
What airlines fly to Chicago Midway Airport?
Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Caribbean according to our data. Southwest is the first choice among our users, with 47% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
Cheap Caribbean to Chicago Midway Airport flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Caribbean to Chicago Midway Airport
When did momondo last update prices for flights from Caribbean to Chicago Midway Airport?
Prices for flights from Caribbean to Chicago Midway Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Caribbean to Chicago Midway Airport?
There are 2 operators available for flights from Caribbean to Chicago Midway Airport as of April 2025.
How old do you have to be to fly from Caribbean to Chicago Midway Airport?
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 Caribbean to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The necessary travel and health documents for your Chicago Midway Airport 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 Caribbean to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from Caribbean to Chicago Midway Airport is Boeing 737-800, representing 25.49% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 23.53%, Airbus A320neo at 11.76%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 11.76%.
Best airlines flying from Caribbean to Chicago Midway Airport
Compare and see reviews for airlines that fly from Caribbean to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $148 | Free Cancellation | Rating 5.9 3,287 reviews | |||
| PriceFrom $312 | Free Cancellation | Rating 8.0 4,294 reviews | |||
| PriceFrom $332 | Free Cancellation | Rating 8.0 7,936 reviews |
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Why should I use momondo to find a flight deal from Caribbean to Chicago?
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 Caribbean to Chicago for you.
Can I find flights from Caribbean to Chicago with flexible booking policies on momondo?
Yes. All flights to Chicago from Caribbean on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Caribbean to Chicago?
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 Caribbean to Chicago.
I’m not ready to book a flight from Caribbean to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Caribbean. 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.