$262 Cheap Flights from Providenciales (PLS) to Chicago (MDW)

View $262 flight on Wed, Dec 10, 2025Opens in a new window

Popular airlines from Providenciales Intl. Airport (PLS) to Chicago Midway Airport (MDW)

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Cheap Flights from Providenciales to Chicago (PLS-MDW)

Prices were available within the past 7 days and start at $262 for one-way flights and $542 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Thu, Jul 24 - Mon, Jul 28
PLS
Providenciales
MDW
Chicago
$542 Roundtrip, found 2 days ago
$542
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Jul 24 from Providenciales to Chicago, returning Mon, Jul 28, priced at $542 found 2 days ago
Southwest Airlines
Thu, Jul 24 - Sun, Jul 27
PLS
Providenciales
MDW
Chicago
$546 Roundtrip, found 6 days ago
$546
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Jul 24 from Providenciales to Chicago, returning Sun, Jul 27, priced at $546 found 6 days ago
Southwest Airlines
Wed, Nov 26 - Tue, Dec 2
PLS
Providenciales
MDW
Chicago
$549 Roundtrip, found 3 days ago
$549
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Nov 26 from Providenciales to Chicago, returning Tue, Dec 2, priced at $549 found 3 days ago
Southwest Airlines
Thu, Jul 24 - Mon, Jul 28
PLS
Providenciales
MDW
Chicago
$555 Roundtrip, found 2 days ago
$555
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Jul 24 from Providenciales to Chicago, returning Mon, Jul 28, priced at $555 found 2 days ago
Southwest Airlines
Thu, Jul 24 - Sun, Jul 27
PLS
Providenciales
MDW
Chicago
$559 Roundtrip, found 6 days ago
$559
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Jul 24 from Providenciales to Chicago, returning Sun, Jul 27, priced at $559 found 6 days ago
Southwest Airlines
Thu, Jul 24 - Sun, Jul 27
PLS
Providenciales
MDW
Chicago
$560 Roundtrip, found 6 days ago
$560
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Jul 24 from Providenciales to Chicago, returning Sun, Jul 27, priced at $560 found 6 days ago
Southwest Airlines
Wed, Nov 26 - Tue, Dec 2
PLS
Providenciales
MDW
Chicago
$565 Roundtrip, found 3 days ago
$565
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Nov 26 from Providenciales to Chicago, returning Tue, Dec 2, priced at $565 found 3 days ago
Southwest Airlines
Thu, Jul 24 - Mon, Jul 28
PLS
Providenciales
MDW
Chicago
$568 Roundtrip, found 2 days ago
$568
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Jul 24 from Providenciales to Chicago, returning Mon, Jul 28, priced at $568 found 2 days ago
Southwest Airlines
Wed, Nov 26 - Tue, Dec 2
PLS
Providenciales
MDW
Chicago
$570 Roundtrip, found 3 days ago
$570
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Nov 26 from Providenciales to Chicago, returning Tue, Dec 2, priced at $570 found 3 days ago
Delta
Thu, Aug 14 - Mon, Aug 18
PLS
Providenciales
MDW
Chicago
$614 Roundtrip, found 3 days ago
$614
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Aug 14 from Providenciales to Chicago, returning Mon, Aug 18, priced at $614 found 3 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $515
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $515
Flights from Providenciales (PLS) to Chicago (MDW)
Origin airport
Providenciales Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$541
Distance
1648 mi

Providenciales to Chicago Flights

The cheapest times to fly from Providenciales to Chicago

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 Providenciales to Chicago are during the month of July. You can find some of the cheapest flights from Providenciales to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Providenciales to Chicago

Sunday is one of the best days to book for cheap flights from Providenciales to Chicago: 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 Providenciales to Chicago

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 Providenciales to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $262 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 Providenciales to Chicago 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 Providenciales to Chicago 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 Providenciales Intl. Airport (PLS) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from PLS to MDW 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 PLS to MDW?
The cheapest flights from PLS to MDW 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 PLS to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from PLS to MDW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Providenciales Intl. Airport (PLS) to Midway Intl. Airport (MDW)?
You'll have to hop on a flight with a layover when traveling from Providenciales Intl. Airport (PLS) to Midway Intl. Airport (MDW). 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 PLS to MDW?
Usually you'll find the most flight options available on a Friday. Tuesdays tend to be the quietest.* But this can vary depending on the time of year, 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 Providenciales Intl. Airport (PLS) to Midway Intl. Airport (MDW)?
To reach Midway Intl. Airport (MDW) on time, select a flight that takes off from Providenciales Intl. Airport (PLS) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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 Chicago from Providenciales Intl. Airport (PLS)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Providenciales Intl. Airport (PLS). Consider your options and find cheap fares on Expedia.
Is it cheaper to buy a plane ticket from Providenciales Intl. Airport (PLS) to Midway Intl. Airport (MDW) last-minute?
Last-minute bookings from PLS to MDW are generally more expensive. To lock in the lowest prices, start looking for flights as early as possible. That being said, if your travel plans are flexible, you may find a cheap ticket right before you leave.
Is it cheaper to book a PLS to MDW flight and hotel package?
Securing a PLS to MDW flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Pick from our extensive range of accommodations and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Providenciales Intl. Airport (PLS) to Midway Intl. Airport (MDW)?
If you booked your PLS to MDW flight within the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the ticket type 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, go to our Customer Service portal if you want more information.

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*Available to One Key members.