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$56+ Cheap flights from Midway (MDW) to Pittsburgh (PIT)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PIT
Nov 19 — Nov 261
Wed 11/19
Wed 11/26
1 adult, Economy
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Cheap flight deals from Midway to Pittsburgh

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Pittsburgh (PIT). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$157
(Delta)

One-way from

$56
(Southwest)

Popular in

December

Cheapest in

September

Average price

$187

Good round-trip deal

$157 or less

Good one-way deal

$50 or less
Provider with most accurate pricing for Chicago Midway-Pittsburgh flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Pittsburgh flights.
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From Chicago Midway to Pittsburgh
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One-way flight from Chicago Midway to Pittsburgh
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Highest demand for flights based on searches. 25% potential increase in price ($108 potential increase over avg. RT price).
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Cheapest flight prices on average. 13% potential price decrease ($36 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Chicago Midway to Pittsburgh.
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Price to beat on a one-way flight from Chicago Midway to Pittsburgh.
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Find flight deals from Midway to Pittsburgh

Cheapest flights from Midway to Pittsburgh
Explore the most affordable flight options available from Midway to Pittsburgh. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/86:15 amMDW - PIT
2 stops13h 56mMultiple Airlines
Wed 11/1210:06 pmPIT - MDW
1 stop26h 49mMultiple Airlines
Deal found 10/20$160
This Priceline deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/238:25 amMDW - PIT
1 stop4h 16mFrontier
Fri 10/242:45 pmPIT - MDW
1 stop9h 18mFrontier
Deal found 10/19$168
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:26 pmMDW - PIT
1 stop10h 55mMultiple Airlines
Mon 11/1710:15 amPIT - MDW
2 stops15h 15mMultiple Airlines
Deal found 10/20$177
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:30 pmMDW - PIT
Nonstop1h 20mSouthwest
Mon 12/82:00 pmPIT - MDW
Nonstop1h 30mSouthwest
Deal found 10/20$179
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/228:40 pmMDW - PIT
Nonstop1h 25mSouthwest
Mon 11/246:15 amPIT - MDW
Nonstop1h 40mSouthwest
Deal found 10/19$183
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1710:15 amMDW - PIT
Nonstop1h 30mSouthwest
Mon 11/248:10 pmPIT - MDW
Nonstop1h 30mSouthwest
Deal found 10/19$186
This Frontier deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/268:25 amMDW - PIT
1 stop4h 16mFrontier
Mon 10/273:55 pmPIT - MDW
1 stop8h 08mFrontier
Deal found 10/20$188
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:26 pmMDW - PIT
1 stop10h 55mMultiple Airlines
Sun 11/166:45 pmPIT - MDW
1 stop14h 47mMultiple Airlines
Deal found 10/20$194

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Pittsburgh that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 20, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Pittsburgh that are best for you.

Fly from

Midway

Fly to

Pittsburgh

Route

Depart

Return

Price

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Sat 1/17

5:59 pm-10:41 pm

1 stop3h 42m

Pittsburgh

Sun 1/18

2:05 pm-6:34 pm

1 stop5h 29m

$157

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Fri 2/20

10:15 am-12:40 pm

Nonstop1h 25m

Pittsburgh

Mon 2/23

5:40 am-6:30 am

Nonstop1h 50m

$168

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Sat 11/22

8:40 pm-11:05 pm

Nonstop1h 25m

Pittsburgh

Mon 11/24

6:15 am-6:55 am

Nonstop1h 40m

$183

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Sat 12/6

9:45 am-12:10 pm

Nonstop1h 25m

Pittsburgh

Mon 12/8

5:30 am-11:25 am

1 stop6h 55m

$189

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Mon 11/17

10:15 am-12:45 pm

Nonstop1h 30m

Pittsburgh

Mon 11/24

7:20 pm-11:30 pm

1 stop5h 10m

$196

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Fri 10/31

6:35 pm-11:03 pm

1 stop3h 28m

Pittsburgh

Sat 11/8

6:33 pm-10:14 pm

1 stop4h 41m

$204

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Wed 12/24

5:35 am-12:30 pm

1 stop5h 55m

Pittsburgh

Mon 12/29

6:10 am-6:55 am

Nonstop1h 45m

$216

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Tue 11/11

6:05 pm-8:30 pm

Nonstop1h 25m

Pittsburgh

Wed 11/12

6:40 am-7:20 am

Nonstop1h 40m

$231

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Sun 2/15

11:50 am-5:05 pm

1 stop4h 15m

$56

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Wed 12/24

5:35 am-12:30 pm

1 stop5h 55m

$56

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/19

Showing 1-10 of 19 results
1
2

Compare providers for flights from Midway to Pittsburgh

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Pittsburgh in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Pittsburgh flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Pittsburgh flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Pittsburgh flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Pittsburgh flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Pittsburgh flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Pittsburgh

Have a flexible travel schedule? Discover the best time to fly to Pittsburgh from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Pittsburgh

What is the cheapest month to book a flight from Chicago Midway Airport to Pittsburgh?

Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Pittsburgh (average of $99). Flying from Chicago Midway Airport to Pittsburgh in December is currently the most expensive (average of $567). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to PIT?

Find hourly flight availability from Midway to Pittsburgh. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 20, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 15% on flights from Chicago Midway Airport to Pittsburgh by exploring options for tickets in the afternoon.

The best insider tips for Chicago Midway Airport to Pittsburgh flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Pittsburgh trip
Airports
MDW

Use the mobile ordering system at MDW to get food delivered to your gate, ensuring you don't miss your boarding group on Southwest flights.

Read more about MDWby Ramsey Qubein
PIT

Take the 28X Airport Flyer bus from PIT to downtown Pittsburgh for a budget-friendly option, running twice an hour and taking about 45 minutes.

Read more about PITby John Walton
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
John Walton

John Walton

Expert on PIT

John Walton

John Walton

Independent aviation journalist John Walton took his first flight at eight weeks old and hasn’t stopped travelling since. A world-renowned expert in airlines and the passenger experience, he writes in depth on aviation, is a resident expert on travel in Japan and France, and offers a uniquely queer perspective on travelling the world.

Read more

Reviews of airlines servicing Pittsburgh

Get insights into the airlines that provide service to Pittsburgh. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Pittsburgh. Reviews last updated October 20, 2025.
Read reviews from past customers who have flown Southwest from Chicago Midway Airport to Pittsburgh. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,239 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,239 reviews
Southwest
8.0
Very good
4,239 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midway to Pittsburgh. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Pittsburgh from Chicago Midway?

    Pittsburgh (PIT), located 13.5 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to Pittsburgh. 1 airline have flights to Pittsburgh from Chicago Midway on a regular basis. Booking flights from Chicago Midway to Pittsburgh should not be difficult; the airport handles an average of 3 inbound flights from Chicago Midway per day.

  • How long is the flight from Chicago Midway Airport to Pittsburgh?

    Airlines like Delta and Southwest fly from Chicago Midway Airport to Pittsburgh in about 1h 25m. The time it takes to get you to your destination can typically vary by up to 2h 17m. The distance from Chicago Midway Airport to Pittsburgh is about 400 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly from Chicago Midway Airport to Pittsburgh round-trip?

    Currently priced at $103, Southwest will fly you from Chicago Midway Airport to Pittsburgh and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. Southwest is currently priced 67% below the average price you’ll pay for this route.

  • What are the cheapest flights from Chicago Midway Airport to Pittsburgh?

    While on average a flight from Chicago Midway Airport to Pittsburgh is generally $284, our data shows the cheapest flight currently is $48. When looking at the most popular route, (Chicago Midway - Pittsburgh), you can expect to pay $157 for that flight.

  • Can I find deals for flights from Midway to Pittsburgh that include hotel bookings?

    Yes. In addition to deals on Midway to Pittsburgh flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Pittsburgh?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Pittsburgh.

  • Can I find deals for business class flights from Midway to Pittsburgh?

    Yes. Cheapflights offers flight deals from Midway to Pittsburgh by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Pittsburgh?

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Pittsburgh (average of $99). Flying from Chicago Midway Airport to Pittsburgh in December is currently the most expensive (average of $567). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Pittsburgh?

Book flights to Pittsburgh if you plan to visit one of these locations
Mars
Steubenville
Monroeville
Washington
Wexford
Belle Vernon

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Alternative routes for Midway to Pittsburgh

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Midway to Pittsburgh

Discover the top airline that operate flights from Midway to Pittsburgh. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$103Average$303FlexibilityNo cancel feeOn-time63%

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