HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Pittsburgh

$49+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PIT
Oct 19 — Oct 261
Sun 10/19
Sun 10/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Pittsburgh with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 19, 2025.

Round-trip from

$107
(Southwest)

One-way from

$49
(Southwest)

Popular in

December

Cheapest in

October

Average price

$131

Good round-trip deal

$97 or less

Good one-way deal

$99 or less
From Chicago Midway to Pittsburgh
Search Deals
One-way flight from Chicago Midway to Pittsburgh
Search Deals
Highest demand for flights based on searches. 30% potential increase in price ($139 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Pittsburgh.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Pittsburgh.
Search Deals

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 September 19, 2025.

This Southwest deal was found by Cheapflights users on 9/17. 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 10/169:30 amMDW - PIT
Nonstop1h 25mSouthwest
Mon 10/205:50 pmPIT - MDW
1 stop7h 05mSouthwest
Deal found 9/17$107
This Frontier deal was found by Cheapflights users on 9/17. 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.
Mon 9/298:15 amMDW - PIT
1 stop4h 17mFrontier
Mon 10/273:55 pmPIT - MDW
1 stop8h 08mFrontier
Deal found 9/17$144
This Booking.com deal was found by Cheapflights users on 9/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/268:15 amMDW - PIT
1 stop4h 17mFrontier
Sun 9/2810:24 amPIT - MDW
1 stop21h 59mFrontier
Deal found 9/17$156
This Southwest deal was found by Cheapflights users on 9/17. 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 10/141:25 pmMDW - PIT
Nonstop1h 20mSouthwest
Fri 10/176:20 amPIT - MDW
Nonstop1h 30mSouthwest
Deal found 9/17$158
This Booking.com deal was found by Cheapflights users on 9/18. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/319:32 amMDW - PIT
1 stop7h 34mFrontier
Sun 11/26:45 pmPIT - MDW
1 stop14h 47mFrontier
Deal found 9/18$170
This Delta deal was found by Cheapflights users on 9/18. 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.
Thu 10/169:35 amMDW - PIT
1 stop5h 33mDelta
Thu 10/236:00 amPIT - MDW
1 stop4h 40mDelta
Deal found 9/18$177
This Booking.com deal was found by Cheapflights users on 9/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/38:15 amMDW - PIT
1 stop4h 17mFrontier
Sun 10/510:24 amPIT - MDW
1 stop21h 59mFrontier
Deal found 9/17$192
This Delta deal was found by Cheapflights users on 9/17. 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.
Thu 10/169:35 amMDW - PIT
1 stop5h 33mDelta
Fri 10/176:36 pmPIT - MDW
1 stop4h 38mDelta
Deal found 9/17$208

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 September 19, 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 10/16

9:30 am-11:55 am

Nonstop1h 25m

Pittsburgh

Thu 10/23

6:00 pm-10:20 pm

1 stop5h 20m

$107

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Thu 10/16

8:25 am-1:41 pm

1 stop4h 16m

Pittsburgh

Sun 10/19

5:33 pm-12:36 am

1 stop8h 03m

$144

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Tue 10/14

1:25 pm-3:45 pm

Nonstop1h 20m

Pittsburgh

Fri 10/17

6:20 am-6:50 am

Nonstop1h 30m

$158

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Tue 10/28

4:10 pm-9:30 pm

1 stop4h 20m

Pittsburgh

Fri 10/31

12:50 pm-1:15 pm

Nonstop1h 25m

$168

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Thu 10/16

9:35 am-4:08 pm

1 stop5h 33m

Pittsburgh

Thu 10/23

6:35 am-8:40 am

1 stop3h 05m

$177

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Wed 10/15

6:00 am-12:43 pm

1 stop5h 43m

Pittsburgh

Wed 10/22

6:36 pm-10:14 pm

1 stop4h 38m

$177

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Thu 10/16

1:30 pm-3:50 pm

Nonstop1h 20m

Pittsburgh

Sun 10/19

10:30 am-10:55 am

Nonstop1h 25m

$221

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Tue 12/30

5:59 pm-11:39 pm

1 stop4h 40m

Pittsburgh

Wed 12/31

7:00 am-11:06 am

1 stop5h 06m

$238

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Sat 1/17

9:30 am-1:24 pm

1 stop2h 54m

Pittsburgh

Sun 1/18

6:00 am-8:50 am

1 stop3h 50m

$239

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Tue 10/14

8:45 pm-11:05 pm

Nonstop1h 20m

$49

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/18

Showing 1-10 of 20 results
1
2

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 September 19, 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 morning.

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 September 19, 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
4,242 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

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 2 inbound flights from Chicago Midway per day.

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

    Airlines like Southwest and Frontier 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 51m. 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 $211, our data shows the cheapest flight currently is $38. 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 Pittsburgh?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 John F Kennedy Intl flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Newark flights
O'Hare Intl to Reagan-National flights
Midway to LaGuardia flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to Dulles Intl flights
Midway to John F Kennedy Intl flights
Midway to Newark flights
Midway to Dulles Intl flights
Midway to Philadelphia flights
Midway to Reagan-National flights
O'Hare Intl to Pittsburgh flights
O'Hare Intl to Harrisburg flights
O'Hare Intl to Scranton flights
Midway to Harrisburg flights
O'Hare Intl to Allentown flights
O'Hare Intl to State College flights
Midway to Allentown flights
O'Hare Intl to Elmira flights
O'Hare Intl to Erie flights
O'Hare Intl to Latrobe flights
Midway to Scranton flights
O'Hare Intl to Williamsport flights
Midway to Erie 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 September 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$103Average$387FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.