$90 Cheap Flights from Chicago (MDW) to Ponce (PSE)

View $90 flight on Thu, Aug 14, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Ponce (PSE-Mercedita)

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Cheap Flights from Chicago to Ponce (MDW-PSE)

Prices were available within the past 7 days and start at $90 for one-way flights and $180 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Aug 14 - Sun, Aug 17
MDW
Chicago
PSE
Ponce
$180 Roundtrip, found 6 days ago
$180
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Aug 14 from Chicago to Ponce, returning Sun, Aug 17, priced at $180 found 6 days ago
Frontier Airlines
Thu, Aug 14 - Mon, Aug 18
MDW
Chicago
PSE
Ponce
$209 Roundtrip, found 6 days ago
$209
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Aug 14 from Chicago to Ponce, returning Mon, Aug 18, priced at $209 found 6 days ago
Frontier Airlines
Thu, Aug 14 - Mon, Aug 18
MDW
Chicago
PSE
Ponce
$228 Roundtrip, found 6 days ago
$228
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Aug 14 from Chicago to Ponce, returning Mon, Aug 18, priced at $228 found 6 days ago
Frontier Airlines
Sat, Jul 19 - Sat, Jul 26
MDW
Chicago
PSE
Ponce
$294 Roundtrip, found 4 hours ago
$294
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Jul 19 from Chicago to Ponce, returning Sat, Jul 26, priced at $294 found 4 hours ago
Frontier Airlines
Thu, Jul 3 - Fri, Jul 11
MDW
Chicago
PSE
Ponce
$296 Roundtrip, found 1 day ago
$296
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Jul 3 from Chicago to Ponce, returning Fri, Jul 11, priced at $296 found 1 day ago
Frontier Airlines
Thu, Jul 3 - Sat, Jul 5
MDW
Chicago
PSE
Ponce
$298 Roundtrip, found 19 hours ago
$298
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Thu, Jul 3 from Chicago to Ponce, returning Sat, Jul 5, priced at $298 found 19 hours ago
Frontier Airlines
Thu, Jul 17 - Thu, Jul 31
MDW
Chicago
PSE
Ponce
$304 Roundtrip, found 2 days ago
$304
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Jul 17 from Chicago to Ponce, returning Thu, Jul 31, priced at $304 found 2 days ago
Frontier Airlines
Thu, Jul 3 - Mon, Jul 7
MDW
Chicago
PSE
Ponce
$306 Roundtrip, found 19 hours ago
$306
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Thu, Jul 3 from Chicago to Ponce, returning Mon, Jul 7, priced at $306 found 19 hours ago
Frontier Airlines
Thu, Jul 17 - Mon, Jul 21
MDW
Chicago
PSE
Ponce
$309 Roundtrip, found 6 days ago
$309
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Jul 17 from Chicago to Ponce, returning Mon, Jul 21, priced at $309 found 6 days ago
Frontier Airlines
Thu, Jul 3 - Sat, Jul 5
MDW
Chicago
PSE
Ponce
$314 Roundtrip, found 1 day ago
$314
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Jul 3 from Chicago to Ponce, returning Sat, Jul 5, priced at $314 found 1 day ago
Flights from Chicago (MDW) to Ponce (PSE)
Origin airport
Midway Intl.
Destination airport
Mercedita
Airlines serving
Frontier Airlines
Roundtrip price
$180
Distance
2063 mi

Chicago to Ponce Flights

The cheapest times to fly from Chicago to Ponce

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Ponce are during the month of August. You can find some of the cheapest flights from Chicago to Ponce with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Ponce

Sunday is one of the best days to book for cheap flights from Chicago to Ponce: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Ponce

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Ponce in 2025. You can also book with separate airlines for your outbound and return journeys, from $90 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Ponce flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Ponce airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Mercedita Airport (PSE) cost?
Discover the latest flight deals from MDW to PSE by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to PSE?
The cheapest flights from MDW to PSE are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from MDW to PSE?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to PSE. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Mercedita Airport (PSE)?
You'll need to book a flight with a layover when traveling from Midway Intl. Airport (MDW) to Mercedita Airport (PSE). Direct flights don't operate daily on this route. However, simply filter your search to include one or two stops to discover the best option for your trip.
What day of the week has the most flights from MDW to PSE?
Typically you'll have the most choice when it comes to flights on a Friday. Tuesdays are often the quietest.* However, this can change based on the season, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Mercedita Airport (PSE)?
To reach Mercedita Airport (PSE) on schedule, pick a flight that takes off from Midway Intl. Airport (MDW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Ponce from Midway Intl. Airport (MDW)?
Explore your flight options from Midway Intl. Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU). This is the only Ponce airport you can arrive at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Mercedita Airport (PSE) last-minute?
Last-minute fares from MDW to PSE are generally more expensive. For the cheapest rates, start looking for flights ahead of time. That being said, if you're flexible with your travel plans, you may score a cheap fare right before you leave.
Is it cheaper to book a MDW to PSE flight and hotel package?
You can save money by securing a MDW to PSE flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one convenient place. Once you've selected your ideal accommodations and flights, you can add extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Mercedita Airport (PSE)?
If you reserved your MDW to PSE flight within the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you want more information.

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*Available to One Key members.