$49 Cheap Flights from Chicago (MDW) to Pittsburgh (PIT)

View $49 flight on Thu, Jan 1, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Pittsburgh Intl. Airport (PIT)

Today's featured flight deals from Chicago Midway Airport (MDW) to Pittsburgh Intl. Airport (PIT)

Nonstop
Carry-on included
Lower price than typical

Cheap Flights from Chicago to Pittsburgh (MDW-PIT)

Prices were available within the past 7 days and start at $49 for one-way flights and $97 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Thu, Dec 25 - Thu, Jan 1
MDW
Chicago
PIT
Pittsburgh
$97 Roundtrip, found 10 hours ago
$97
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Thu, Dec 25 from Chicago to Pittsburgh, returning Thu, Jan 1, priced at $97 found 10 hours ago
Southwest Airlines
Sat, Feb 14 - Thu, Feb 19
MDW
Chicago
PIT
Pittsburgh
$101 Roundtrip, found 4 days ago
$101
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sat, Feb 14 from Chicago to Pittsburgh, returning Thu, Feb 19, priced at $101 found 4 days ago
Southwest Airlines
Thu, Dec 25 - Thu, Jan 1
MDW
Chicago
PIT
Pittsburgh
$107 Roundtrip, found 10 hours ago
$107
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Thu, Dec 25 from Chicago to Pittsburgh, returning Thu, Jan 1, priced at $107 found 10 hours ago
Southwest Airlines
Sat, Jan 17 - Tue, Jan 20
MDW
Chicago
PIT
Pittsburgh
$109 Roundtrip, found 3 days ago
$109
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Jan 17 from Chicago to Pittsburgh, returning Tue, Jan 20, priced at $109 found 3 days ago
Southwest Airlines
Sat, Feb 14 - Thu, Feb 19
MDW
Chicago
PIT
Pittsburgh
$111 Roundtrip, found 4 days ago
$111
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sat, Feb 14 from Chicago to Pittsburgh, returning Thu, Feb 19, priced at $111 found 4 days ago
Southwest Airlines
Thu, Dec 11 - Wed, Dec 17
MDW
Chicago
PIT
Pittsburgh
$112 Roundtrip, found 11 hours ago
$112
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Thu, Dec 11 from Chicago to Pittsburgh, returning Wed, Dec 17, priced at $112 found 11 hours ago
Southwest Airlines
Thu, Dec 11 - Wed, Dec 17
MDW
Chicago
PIT
Pittsburgh
$117 Roundtrip, found 11 hours ago
$117
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Thu, Dec 11 from Chicago to Pittsburgh, returning Wed, Dec 17, priced at $117 found 11 hours ago
Southwest Airlines
Sat, Jan 17 - Tue, Jan 20
MDW
Chicago
PIT
Pittsburgh
$119 Roundtrip, found 3 days ago
$119
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Jan 17 from Chicago to Pittsburgh, returning Tue, Jan 20, priced at $119 found 3 days ago
Delta
Thu, Dec 25 - Thu, Jan 1
MDW
Chicago
PIT
Pittsburgh
$127 Roundtrip, found 10 hours ago
$127
Roundtrip
found 10 hours ago
Select Delta flight, departing Thu, Dec 25 from Chicago to Pittsburgh, returning Thu, Jan 1, priced at $127 found 10 hours ago
Frontier Airlines
Sun, Nov 9 - Fri, Nov 14
MDW
Chicago
PIT
Pittsburgh
$206 Roundtrip, found 1 day ago
$206
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Nov 9 from Chicago to Pittsburgh, returning Fri, Nov 14, priced at $206 found 1 day ago

Find the cheapest month to fly from Chicago (MDW) to Pittsburgh (PIT)

September is typically the cheapest month to fly

From $77 - $466 per traveler.

Alternative airports near Pittsburgh

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

Select flight to Pittsburgh Intl. PIT. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $479
PIT
Pittsburgh Intl.
Cheapest
Average driving time to city center23 min
Flights from $479
Flights from Chicago (MDW) to Pittsburgh (PIT)
Origin airport
Midway Intl.
Destination airport
Pittsburgh Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$97
Distance
399 mi
Average flight time
2 hours 21 mins

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 December. 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 $49 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?
Snag a cheap one-way flight from $49 or cheap return flight from $97 from Midway Intl. Airport (MDW) to Pittsburgh Intl. Airport (PIT) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Pittsburgh Intl. Airport (PIT)?
Flying in December can help you save, as it's the cheapest month for flights between MDW and PIT. You'll typically find the lowest prices during the off-season.
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 Midway Intl. Airport (MDW) to Pittsburgh Intl. Airport (PIT)?
To find the cheapest airline flying from MDW to PIT, use Expedia's filter tool. Tailor your search based on your travel style, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
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.