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Midway

$69+ Cheap flights from Pittsburgh (PIT) to Midway (MDW)

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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — MDW
Apr 17 — Apr 241
Fri 4/17
Fri 4/24
1 adult, Economy
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Cheap flight deals from Pittsburgh to Midway

Cheapest flights from Pittsburgh to Midway
Explore the most affordable flight options available from Pittsburgh to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 18, 2026.

This Southwest deal was found by Cheapflights users on 3/16. 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 4/2110:50 am
PIT
-
MDW
2 stops7h 15m
Southwest
Sat 4/257:45 am
MDW
-
PIT
Nonstop1h 20m
Southwest
Deal found 3/16$172
This Southwest deal was found by Cheapflights users on 3/16. 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 4/98:00 pm
PIT
-
MDW
Nonstop1h 30m
Southwest
Mon 4/136:55 pm
MDW
-
PIT
Nonstop1h 25m
Southwest
Deal found 3/16$177
This Southwest deal was found by Cheapflights users on 3/14. 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 4/186:00 am
PIT
-
MDW
2 stops9h 40m
Southwest
Mon 4/206:55 pm
MDW
-
PIT
Nonstop1h 25m
Southwest
Deal found 3/14$192
This Delta deal was found by Cheapflights users on 3/16. 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 4/912:22 pm
PIT
-
MDW
1 stop7h 18m
Delta
Mon 4/136:38 pm
MDW
-
PIT
1 stop3h 18m
Delta
Deal found 3/16$197
This Southwest deal was found by Cheapflights users on 3/16. 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 4/275:45 am
PIT
-
MDW
2 stops8h 25m
Southwest
Sat 5/29:15 am
MDW
-
PIT
2 stops10h 50m
Southwest
Deal found 3/16$207
This Southwest deal was found by Cheapflights users on 3/13. 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 4/309:25 am
PIT
-
MDW
1 stop9h 50m
Southwest
Wed 5/62:35 pm
MDW
-
PIT
2 stops6h 35m
Southwest
Deal found 3/13$208
This Southwest deal was found by Cheapflights users on 3/13. 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.
Wed 4/86:25 am
PIT
-
MDW
2 stops10h 20m
Southwest
Tue 4/148:05 am
MDW
-
PIT
2 stops8h 15m
Southwest
Deal found 3/13$213
This Delta deal was found by Cheapflights users on 3/13. 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.
Mon 4/273:55 pm
PIT
-
MDW
1 stop3h 03m
Delta
Mon 5/46:38 pm
MDW
-
PIT
1 stop3h 18m
Delta
Deal found 3/13$217
This Southwest deal was found by Cheapflights users on 3/17. 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.
Sat 5/167:15 am
PIT
-
MDW
2 stops8h 25m
Southwest
Tue 5/192:35 pm
MDW
-
PIT
2 stops6h 35m
Southwest
Deal found 3/17$227

Find flight deals from Pittsburgh to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Pittsburgh (PIT) to Midway (MDW). 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 March 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$172
(Southwest)

One-way from

$69
(Southwest)

Popular in

August

Cheapest in

September

Average price

$304

Good round-trip deal

$338 or less

Good one-way deal

$199 or less
Provider with most accurate pricing for Pittsburgh-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Pittsburgh-Chicago Midway flights.
Search Deals
From Pittsburgh to Chicago Midway
Search Deals
One-way flight from Pittsburgh to Chicago Midway
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Pittsburgh to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Pittsburgh to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pittsburgh to Midway 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 March 18, 2026.
Use the filters below to find and compare flights from Pittsburgh to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 4/9

8:00 pm-8:30 pm

Nonstop1h 30m

Chicago Midway

Mon 4/13

7:40 am-10:00 am

Nonstop1h 20m

$177

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 4/11

8:25 am-8:55 am

Nonstop1h 30m

Chicago Midway

Mon 4/13

7:40 am-10:00 am

Nonstop1h 20m

$177

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 5/6

12:30 pm-7:45 pm

2 stops8h 15m

Chicago Midway

Mon 5/11

12:50 pm-3:15 pm

Nonstop1h 25m

$192

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 5/19

10:50 am-5:05 pm

2 stops7h 15m

Chicago Midway

Wed 5/20

7:50 am-10:15 am

Nonstop1h 25m

$192

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Mon 5/11

8:10 pm-11:30 pm

1 stop4h 20m

Chicago Midway

Thu 5/14

5:30 am-12:15 pm

1 stop5h 45m

$197

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Fri 6/5

5:50 pm-10:00 pm

1 stop5h 10m

Chicago Midway

Mon 6/8

7:50 am-12:30 pm

1 stop3h 40m

$280

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 6/9

6:05 pm-9:45 pm

1 stop4h 40m

Chicago Midway

Thu 6/11

5:59 pm-10:38 pm

1 stop3h 39m

$300

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 5/23

10:31 am-12:42 pm

1 stop3h 11m

Chicago Midway

Sun 5/24

6:36 pm-10:38 pm

1 stop3h 02m

$311

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Fri 5/15

10:05 am-8:05 pm

2 stops11h 00m

Chicago Midway

Mon 5/18

5:40 pm-10:15 pm

1 stop3h 35m

$319
Cheapest one-way
Quickest one-way

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 5/5

1:25 pm-1:55 pm

Nonstop1h 30m

$69

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/17

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

Compare providers for flights from Pittsburgh to Midway

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 Pittsburgh to Midway in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 Pittsburgh-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Pittsburgh-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Pittsburgh-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Pittsburgh-Chicago Midway Airport 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 Pittsburgh-Chicago Midway Airport 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 Pittsburgh to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Pittsburgh 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 Pittsburgh to Chicago Midway Airport

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

Currently, November is the cheapest month in which you can book a flight from Pittsburgh to Chicago Midway Airport (average of $76). Flying from Pittsburgh to Chicago Midway Airport in February is currently the most expensive (average of $270). 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 PIT to MDW?

Find hourly flight availability from Pittsburgh to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 18, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 12% on flights from Pittsburgh to Chicago Midway Airport by exploring options for tickets at noon.

What is the cheapest day to fly from Pittsburgh to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Pittsburgh to Midway. Price data was last updated on March 14, 2026.

Travelers seeking maximum savings on their Pittsburgh to Chicago Midway Airport flight should consider departing on Tuesday at noon when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for Pittsburgh to Chicago Midway Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Pittsburgh to Chicago Midway Airport trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

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

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 Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated March 18, 2026.
Read through reviews of airlines operating flights from Pittsburgh to Chicago Midway Airport, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,320 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

KOA - HNL

pretty smooth and fast service ever, that flight is very helpful each and everyone for price and also fright for free..
Southwest
8.0
Very good
4,320 reviews
Southwest
8.0
Very good
4,320 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

KOA - HNL

pretty smooth and fast service ever, that flight is very helpful each and everyone for price and also fright for free..

Related info for your journey

Find useful and relevant information for your journey from Pittsburgh to Midway. 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 from for flights from Pittsburgh to Chicago Midway?

    For a flight from Pittsburgh to Chicago Midway, you will be flying from Pittsburgh. Pittsburgh (PIT) is just 13.5 mi from the center of the city. Pittsburgh is the only Pittsburgh airport and it handles 2 outbound flights to Chicago Midway per day. 1 airline has flights to Chicago Midway from Pittsburgh on a regular basis.

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

    Airlines like Southwest fly from Pittsburgh to Chicago Midway Airport in about 1h 30m. The time it takes to get you to your destination is usually consistent. The distance between Pittsburgh and Chicago Midway Airport is about 400 mi. Most flights are nonstop.

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

    Southwest, at $97, was found to be the cheapest airline from Pittsburgh to Chicago Midway Airport.. Southwest is priced at 70% lower than the current average price of a flight leaving 3 months from now.

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

    On average you can expect to pay $345 for a flight from Pittsburgh to Chicago Midway Airport. The cheapest flight overall is $150 while the most popular route, (Pittsburgh - Chicago Midway) is currently priced at $137.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Pittsburgh to Midway 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 Pittsburgh to Chicago Midway Airport?

    Currently, November is the cheapest month in which you can book a flight from Pittsburgh to Chicago Midway Airport (average of $76). Flying from Pittsburgh to Chicago Midway Airport in February is currently the most expensive (average of $270). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Pittsburgh to Midway

Discover the top airline that operate flights from Pittsburgh to Midway. 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 March 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$97Average$327FlexibilityNo cancel feeOn-time63%

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