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$101+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PIT
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$235
(Southwest)

One-way from

$101
(Trip.com)

Popular in

December

Cheapest in

May

Average price

$132

Good round-trip deal

$240 or less

Good one-way deal

$117 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. 26% potential increase in price ($118 potential increase over avg. RT price).
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Cheapest flight prices on average. 10% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Southwest deal was found by Cheapflights users on 4/29. 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.
Tue 5/2010:20 amMDW - PIT
Nonstop1h 20mSouthwest
Tue 5/271:05 pmPIT - MDW
Nonstop1h 30mSouthwest
Deal found 4/29$235
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/36:25 pmMDW - PIT
1 stop3h 28mDelta
Tue 6/1011:01 amPIT - MDW
1 stop7h 39mDelta
Deal found 4/29$255
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/98:35 amMDW - PIT
1 stop9h 52mAllegiant Air
Sat 5/106:00 pmPIT - MDW
1 stop20h 29mAllegiant Air
Deal found 4/30$315
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/68:36 pmMDW - PIT
2 stops26h 18mMultiple Airlines
Sun 6/86:30 amPIT - MDW
2 stops32h 33mMultiple Airlines
Deal found 4/30$324

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 May 1, 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

Tue 5/20

10:20 am-12:40 pm

Nonstop1h 20m

Pittsburgh

Tue 5/27

1:05 pm-1:35 pm

Nonstop1h 30m

$235

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Tue 6/3

6:25 pm-10:53 pm

1 stop3h 28m

Pittsburgh

Tue 6/10

11:01 am-5:40 pm

1 stop7h 39m

$255

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Fri 5/9

8:35 am-7:27 pm

1 stop9h 52m

Pittsburgh

Sat 5/10

6:00 pm-1:29 pm

1 stop20h 29m

$315

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Fri 6/6

8:36 pm-11:54 pm

2 stops26h 18m

Pittsburgh

Sun 6/8

6:30 am-2:03 pm

2 stops32h 33m

$324

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Thu 5/15

1:19 pm-5:24 pm

1 stop27h 05m

$101

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Mon 5/19

9:42 am-9:26 pm

1 stop10h 44m

$105

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Tue 5/20

10:20 am-12:40 pm

Nonstop1h 20m

$118

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Tue 5/20

6:25 pm-10:53 pm

1 stop3h 28m

$128

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Mon 6/9

8:36 pm-11:54 pm

2 stops26h 18m

$145

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Pittsburgh flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Pittsburgh (average of $262). Flying from Chicago Midway Airport to Pittsburgh in November is currently the most expensive (average of $333). 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 May 1, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 33% on flights from Chicago Midway Airport to Pittsburgh by exploring options for tickets in the evening.

Rainfall in Pittsburgh by month

Plan your trip to Pittsburgh by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Pittsburgh ranges from 2.3 - 4.3 inches per month. June is typically the wettest month, when rainfall can reach 4.3 in. October is typically the driest time to visit Pittsburgh when rainfall is around 2.3 in.

Temperature in Pittsburgh by month

Plan your trip to Pittsburgh by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Pittsburgh, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 28.4 F).

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 May 1, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Allegiant Air from Chicago to Pittsburgh by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 2 inbound flights from Chicago Midway per day.

  • What are the cheapest airlines flying from Chicago Midway Airport to Pittsburgh round-trip?

    Currently priced at $235, 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. Check Cheapflights for deals on Delta for as low as $255. Southwest is currently priced 29% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Pittsburgh one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $101. Users have also found prices from $105 and $118 on Allegiant Air and Southwest, respectively.

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

    While on average a flight from Chicago Midway Airport to Pittsburgh is generally $269, our data shows the cheapest flight currently is $117. When looking at the most popular route, (Chicago Midway - Pittsburgh), you can expect to pay $235 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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Pittsburgh (average of $262). Flying from Chicago Midway Airport to Pittsburgh in November is currently the most expensive (average of $333). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Monroeville
Washington
Steubenville
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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$103Average$315FlexibilityNo cancel feeOn-time63%

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