$39 Cheap Flights from Chicago (MDW) to Pittsburgh (PIT)

View $39 flight on Wed, Jul 23, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Pittsburgh (MDW-PIT)

Prices were available within the past 7 days and start at $39 for one-way flights and $77 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
MDW
Chicago
PIT
Pittsburgh
$77 Roundtrip, found 2 hours ago
$77
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Thu, Jul 24 from Chicago to Pittsburgh, returning Mon, Jul 28, priced at $77 found 2 hours ago
Southwest Airlines
Thu, May 22 - Mon, May 26
MDW
Chicago
PIT
Pittsburgh
$87 Roundtrip, just found
$87
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, May 22 from Chicago to Pittsburgh, returning Mon, May 26, priced at $87 just found
Southwest Airlines
Thu, Jul 3 - Mon, Jul 7
MDW
Chicago
PIT
Pittsburgh
$97 Roundtrip, found 21 hours ago
$97
Roundtrip
found 21 hours ago
Select Southwest Airlines flight, departing Thu, Jul 3 from Chicago to Pittsburgh, returning Mon, Jul 7, priced at $97 found 21 hours ago
Southwest Airlines
Mon, Aug 11 - Thu, Aug 14
MDW
Chicago
PIT
Pittsburgh
$97 Roundtrip, found 4 days ago
$97
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Mon, Aug 11 from Chicago to Pittsburgh, returning Thu, Aug 14, priced at $97 found 4 days ago
Southwest Airlines
Tue, Aug 26 - Wed, Aug 27
MDW
Chicago
PIT
Pittsburgh
$102 Roundtrip, found 2 days ago
$102
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Aug 26 from Chicago to Pittsburgh, returning Wed, Aug 27, priced at $102 found 2 days ago
Southwest Airlines
Mon, Aug 11 - Tue, Aug 12
MDW
Chicago
PIT
Pittsburgh
$107 Roundtrip, found 4 days ago
$107
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Mon, Aug 11 from Chicago to Pittsburgh, returning Tue, Aug 12, priced at $107 found 4 days ago
Southwest Airlines
Thu, May 22 - Mon, May 26
MDW
Chicago
PIT
Pittsburgh
$117 Roundtrip, just found
$117
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, May 22 from Chicago to Pittsburgh, returning Mon, May 26, priced at $117 just found
Southwest Airlines
Thu, Jul 3 - Mon, Jul 7
MDW
Chicago
PIT
Pittsburgh
$127 Roundtrip, found 21 hours ago
$127
Roundtrip
found 21 hours ago
Select Southwest Airlines flight, departing Thu, Jul 3 from Chicago to Pittsburgh, returning Mon, Jul 7, priced at $127 found 21 hours ago
Delta
Thu, May 22 - Mon, May 26
MDW
Chicago
PIT
Pittsburgh
$127 Roundtrip, just found
$127
Roundtrip
just found
Select Delta flight, departing Thu, May 22 from Chicago to Pittsburgh, returning Mon, May 26, priced at $127 just found
Frontier Airlines
Sat, Jul 26 - Mon, Jul 28
MDW
Chicago
PIT
Pittsburgh
$151 Roundtrip, found 2 days ago
$151
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Jul 26 from Chicago to Pittsburgh, returning Mon, Jul 28, priced at $151 found 2 days ago
Flights from Chicago (MDW) to Pittsburgh (PIT)
Origin airport
Midway Intl.
Destination airport
Pittsburgh Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$77
Distance
399 mi

Chicago to Pittsburgh Flights

The cheapest times to fly from Chicago to Pittsburgh

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

The best time to book a flight from Chicago to Pittsburgh

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

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 Pittsburgh in 2025. You can also book with separate airlines for your outbound and return journeys, from $39 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 Pittsburgh 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 Pittsburgh 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 Pittsburgh Intl. Airport (PIT) cost?
You can find cheap return fares from Midway Intl. Airport (MDW) to Pittsburgh Intl. Airport (PIT) starting from $166. Reserve your seat and be on your way. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and American Airlines flight leaving MDW on May 20 2025 and touching down at PIT. The price was last updated on April 23 2025 and has not changed since.
What is the cheapest month to fly from MDW to PIT?
The cheapest flights from MDW to PIT are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to Pittsburgh Intl. Airport (PIT)?
When flying out of Midway Intl. Airport (MDW), you can take a nonstop flight to Pittsburgh Intl. Airport (PIT) with Southwest Airlines.
What is the cheapest airline that flies from MDW to PIT?
Jet off from MDW to PIT with Southwest Airlines. This airline currently offers the cheapest one-way ticket on this route, starting at $49. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on June 2 2025. Prices were last updated on April 23 2025 and have not changed since.
How many flights per day from Midway Intl. Airport (MDW) to Pittsburgh Intl. Airport (PIT)?
With an average of 2 nonstop flights departing from Midway Intl. Airport (MDW) to Pittsburgh Intl. Airport (PIT) every day, you’ll be off on your next adventure in no time.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Pittsburgh Intl. Airport (PIT)?
More passengers fly between MDW and PIT at 1 PM than at any other point in the day. Rather go when it’s quieter? Try choosing a quieter departure window and you could save on your fare as well.
What day of the week has the most flights from MDW to PIT?
If you fly on a Wednesday, you’ll get the largest range of choices for flights from Midway Intl. Airport (MDW) to Pittsburgh Intl. Airport (PIT).
What is the earliest flight from Midway Intl. Airport (MDW) to Pittsburgh Intl. Airport (PIT)?
Midway Intl. Airport (MDW)’s first flight to Pittsburgh Intl. Airport (PIT) departs at approximately 8:40AM UTC-6. With a total travel time of 1h 25m, you’ll arrive at around 11:05AM UTC-5.
How long does it take to fly from Midway Intl. Airport (MDW) to Pittsburgh Intl. Airport (PIT)?
The average flight time from MDW to PIT is 1 hour and 20 minutes, covering a distance of 400 mi.
What is the best time to fly from Midway Intl. Airport (MDW) to Pittsburgh Intl. Airport (PIT)?
To arrive at Pittsburgh Intl. Airport (PIT) without delays, choose a flight that takes off from Midway Intl. Airport (MDW) before 3 PM. The chance 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 Pittsburgh from Midway Intl. Airport (MDW)?
Pittsburgh Intl. Airport (PIT) is the only airport in Pittsburgh with direct flights from Midway Intl. Airport (MDW). Explore the available options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Pittsburgh Intl. Airport (PIT) last-minute?
Last-minute fares from MDW to PIT are typically more expensive. To lock in the best prices, start searching for flights well ahead of time. That being said, if you can play around with your travel dates, it’s possible to score a cheap ticket right before your trip.
Is it cheaper to book a MDW to PIT flight and hotel package?
Booking a MDW to PIT flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels in one place. Select from our wide 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 Midway Intl. Airport (MDW) to Pittsburgh Intl. Airport (PIT)?
If you reserved your MDW to PIT flight in the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the type of fare you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you’d like more information.

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*Available to One Key members.