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$103+ 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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PIT
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$158
(Southwest)

One-way from

$103
(FlightHub)

Popular in

December

Cheapest in

February

Average price

$425

Good round-trip deal

$265 or less

Good one-way deal

$132 or less
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. 18% potential increase in price ($86 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/10. 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 9/136:35 amMDW - PIT
1 stop5h 35mSouthwest
Mon 9/157:00 pmPIT - MDW
Nonstop1h 25mSouthwest
Deal found 6/10$158
This Delta deal was found by Cheapflights users on 6/10. 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.
Sat 9/136:00 amMDW - PIT
1 stop5h 54mDelta
Tue 9/164:30 pmPIT - MDW
1 stop6h 14mDelta
Deal found 6/10$198
This Priceline deal was found by Cheapflights users on 6/12. 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.
Sat 6/149:12 pmMDW - PIT
1 stop10h 53mFrontier
Mon 6/163:49 pmPIT - MDW
1 stop9h 02mFrontier
Deal found 6/12$228
This Mytrip deal was found by Cheapflights users on 6/10. 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 7/188:03 amMDW - PIT
1 stop6h 09mMultiple Airlines
Sun 7/206:30 amPIT - MDW
2 stops28h 11mMultiple Airlines
Deal found 6/10$259
This Mytrip deal was found by Cheapflights users on 6/12. 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.
Sun 7/2711:37 amMDW - PIT
1 stop11h 02mAllegiant Air
Sun 8/36:30 amPIT - MDW
2 stops32h 26mAllegiant Air
Deal found 6/12$320

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 June 12, 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 8/9

9:50 am-12:15 pm

Nonstop1h 25m

Pittsburgh

Tue 8/12

12:05 pm-4:25 pm

1 stop5h 20m

$158

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Thu 8/7

6:00 am-12:46 pm

1 stop5h 46m

Pittsburgh

Mon 8/11

5:56 pm-9:49 pm

1 stop4h 53m

$238

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Fri 7/18

8:03 am-3:12 pm

1 stop6h 09m

Pittsburgh

Sun 7/20

6:30 am-9:41 am

2 stops28h 11m

$259

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Fri 7/11

8:35 am-6:40 pm

1 stop9h 05m

Pittsburgh

Sun 7/13

9:56 am-3:06 pm

1 stop6h 10m

$299

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Sun 7/27

11:37 am-11:39 pm

1 stop11h 02m

Pittsburgh

Sun 8/3

6:30 am-1:56 pm

2 stops32h 26m

$320

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Fri 8/22

9:17 am-8:01 pm

1 stop9h 44m

$103

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Sat 8/9

9:24 am-4:11 pm

1 stop5h 47m

$110

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Fri 7/4

8:03 am-3:12 pm

1 stop6h 09m

$112

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Sat 7/12

2:30 pm-4:55 pm

Nonstop1h 25m

$115

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Fri 8/1

1:11 pm-11:29 pm

2 stops33h 18m

$124

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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

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 June 12, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 14% 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 June 12, 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
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.3
Good
725 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
6.0
Okay
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

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

    Currently priced at $158, 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. Search Cheapflights for deals from Delta and Frontier - these airlines can fly you to your destination from $238 and $299, respectively. Southwest is currently priced 57% 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 $103. Users have also found prices from $110 and $112 on Delta and Allegiant Air, 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 $345, our data shows the cheapest flight currently is $117. When looking at the most popular route, (Chicago Midway - Pittsburgh), you can expect to pay $97 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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Midway to LaGuardia flights
Midway to Dulles Intl flights
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Midway to Reagan-National flights
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Midway to Erie flights
Midway to Scranton flights
Midway to State College flights

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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$117Average$414FlexibilityNo cancel feeOn-time63%

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