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$61+ 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PIT
Aug 6 — Aug 131
Wed 8/6
Wed 8/13
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 August 1, 2025.

Round-trip from

$104
(Southwest)

One-way from

$61
(Southwest)

Popular in

December

Cheapest in

February

Average price

$254

Good round-trip deal

$97 or less

Good one-way deal

$115 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. 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 ($33 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 1, 2025.

This Southwest deal was found by Cheapflights users on 7/31. 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.
Thu 9/119:30 amMDW - PIT
Nonstop1h 25mSouthwest
Wed 9/171:10 pmPIT - MDW
1 stop4h 55mSouthwest
Deal found 7/31$104
This Delta deal was found by Cheapflights users on 7/31. 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 9/139:35 amMDW - PIT
1 stop2h 52mDelta
Tue 9/164:21 pmPIT - MDW
1 stop6h 15mDelta
Deal found 7/31$177
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/29:12 pmMDW - PIT
1 stop10h 49mFrontier
Mon 8/43:49 pmPIT - MDW
1 stop9h 02mFrontier
Deal found 7/30$188

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 August 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

Thu 9/11

9:30 am-11:55 am

Nonstop1h 25m

Pittsburgh

Wed 9/17

1:10 pm-5:05 pm

1 stop4h 55m

$104

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Sat 9/13

9:35 am-1:27 pm

1 stop2h 52m

Pittsburgh

Tue 9/16

4:21 pm-9:36 pm

1 stop6h 15m

$177

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Sat 8/9

9:12 pm-9:11 am

1 stop10h 59m

Pittsburgh

Mon 8/11

3:49 pm-11:51 pm

1 stop9h 02m

$188

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Wed 10/29

10:10 am-4:55 pm

2 stops5h 45m

$61

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Tue 10/28

10:35 am-7:01 pm

1 stop7h 26m

$89

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Sat 8/9

9:12 pm-9:11 am

1 stop10h 59m

$97

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Mon 9/8

7:50 pm-11:23 pm

3 stops26h 33m

$154

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 $332). 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 August 1, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 18% on flights from Chicago Midway Airport to Pittsburgh by exploring options for tickets in the evening.

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 August 1, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Frontier 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
4,246 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,239 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 1 inbound flight from Chicago Midway per day.

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

    Currently priced at $104, 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 $177 and $188, respectively. Southwest is currently priced 68% 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 Southwest. According to our data, you can fly for as low as $61. Users have also found prices from $89 and $97 on Delta and Frontier, 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 $158, our data shows the cheapest flight currently is $45. When looking at the most popular route, (Chicago Midway - Pittsburgh), you can expect to pay $91 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 $332). 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.
O'Hare Intl to LaGuardia flights
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Midway to LaGuardia flights
Midway to Newark flights
O'Hare Intl to Reagan-National flights
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Midway to John F Kennedy Intl flights
O'Hare Intl to Philadelphia flights
Midway to Dulles Intl flights
O'Hare Intl to Pittsburgh flights
O'Hare Intl to Harrisburg flights
Midway to Philadelphia flights
Midway to Reagan-National flights
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Midway to Harrisburg flights
Midway to Allentown flights
O'Hare Intl to Elmira flights
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O'Hare Intl to Williamsport flights
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 August 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$116Average$414FlexibilityNo cancel feeOn-time63%

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