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Midway

$49+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — MDW
Oct 19 — Oct 261
Sun 10/19
Sun 10/26
1 adult, Economy
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Cheap 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 September 19, 2025.

Round-trip from

$97
(Southwest)

One-way from

$49
(Southwest)

Popular in

August

Cheapest in

December

Average price

$286

Good round-trip deal

$272 or less

Good one-way deal

$175 or less
From Pittsburgh to Chicago Midway
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One-way flight from Pittsburgh to Chicago Midway
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Highest demand for flights based on searches. 11% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Pittsburgh to Chicago Midway.
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Price to beat on a one-way flight from Pittsburgh to Chicago Midway.
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Find 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 September 19, 2025.

This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/94:30 pmPIT - MDW
Nonstop1h 25mSouthwest
Mon 10/139:55 pmMDW - PIT
Nonstop1h 20mSouthwest
Deal found 9/18$97
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.
Sat 10/114:35 pmPIT - MDW
Nonstop1h 25mSouthwest
Sat 10/1811:45 amMDW - PIT
1 stop7h 00mSouthwest
Deal found 9/17$107
This Southwest deal was found by Cheapflights users on 9/16. 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 10/146:10 amPIT - MDW
2 stops9h 15mSouthwest
Wed 10/159:05 amMDW - PIT
2 stops7h 55mSouthwest
Deal found 9/16$127
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/155:50 amPIT - MDW
2 stops9h 15mSouthwest
Sat 10/188:20 amMDW - PIT
2 stops10h 25mSouthwest
Deal found 9/18$133
This Booking.com deal was found by Cheapflights users on 9/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:51 pmPIT - MDW
1 stop16h 35mFrontier
Sun 11/210:12 amMDW - PIT
1 stop6h 38mFrontier
Deal found 9/16$156
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/208:10 pmPIT - MDW
Nonstop1h 30mSouthwest
Wed 10/2210:05 amMDW - PIT
Nonstop1h 20mSouthwest
Deal found 9/18$157
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/108:10 pmPIT - MDW
Nonstop1h 30mSouthwest
Mon 10/139:55 pmMDW - PIT
Nonstop1h 20mSouthwest
Deal found 9/18$158
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/269:34 amPIT - MDW
1 stop25h 17mFrontier
Mon 9/298:15 amMDW - PIT
1 stop4h 17mFrontier
Deal found 9/17$159
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:51 pmPIT - MDW
2 stops16h 35mMultiple Airlines
Tue 11/46:26 pmMDW - PIT
1 stop23h 55mMultiple Airlines
Deal found 9/18$164
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/113:50 pmPIT - MDW
1 stop6h 05mSouthwest
Wed 10/151:25 pmMDW - PIT
Nonstop1h 20mSouthwest
Deal found 9/17$166

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 September 19, 2025.
Use the filters below to find and compare flights from Pittsburgh to Chicago Midway Airport that are best for you.

Fly from

Pittsburgh

Fly to

Midway

Route

Depart

Return

Price

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 10/14

6:45 pm-7:15 pm

Nonstop1h 30m

Chicago Midway

Wed 10/15

7:55 am-12:25 pm

1 stop3h 30m

$107

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 11/11

5:45 am-10:10 am

1 stop5h 25m

Chicago Midway

Wed 11/12

6:05 pm-8:30 pm

Nonstop1h 25m

$107

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 10/11

4:35 pm-5:00 pm

Nonstop1h 25m

Chicago Midway

Wed 10/15

10:05 am-12:25 pm

Nonstop1h 20m

$156

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Fri 10/10

6:20 am-6:50 am

Nonstop1h 30m

Chicago Midway

Sat 10/11

5:35 pm-7:55 pm

Nonstop1h 20m

$158

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Fri 10/10

4:30 pm-4:55 pm

Nonstop1h 25m

Chicago Midway

Mon 10/13

9:55 pm-12:15 am

Nonstop1h 20m

$158

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Mon 11/10

5:15 pm-8:35 pm

1 stop4h 20m

Chicago Midway

Fri 11/14

9:50 pm-12:10 am

Nonstop1h 20m

$168

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 10/16

6:35 am-8:40 am

1 stop3h 05m

Chicago Midway

Tue 10/21

10:35 am-3:55 pm

1 stop4h 20m

$177

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 10/25

6:20 am-10:30 am

1 stop5h 10m

Chicago Midway

Tue 10/28

6:00 am-12:43 pm

1 stop5h 43m

$177

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 10/18

6:20 am-6:50 am

Nonstop1h 30m

$49

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 12/4

6:40 am-7:20 am

Nonstop1h 40m

$49

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/18

Showing 1-10 of 17 results
1
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The best insider tips for Pittsburgh to Chicago Midway Airport 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 Pittsburgh to Chicago Midway Airport trip
Airports
PIT

Arrive early at PIT due to potential construction-related changes and busy morning security lines. Check the airport's live security time tracker for updates.

Read more about PITby John Walton
MDW

Use the Orange Line train for a quick, budget-friendly trip from MDW to downtown Chicago in under 30 minutes.

Read more about MDWby Ramsey Qubein
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 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, April is the cheapest month in which you can book a flight from Pittsburgh to Chicago Midway Airport (average of $160). Flying from Pittsburgh to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 September 19, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 11% on flights from Pittsburgh to Chicago Midway Airport by exploring options for tickets in the afternoon.

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 September 14, 2025.

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

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 September 19, 2025.
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
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

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

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

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 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 3 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 69% 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 $305 for a flight from Pittsburgh to Chicago Midway Airport. The cheapest flight overall is $38 while the most popular route, (Pittsburgh - Chicago Midway) is currently priced at $97.

  • 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, April is the cheapest month in which you can book a flight from Pittsburgh to Chicago Midway Airport (average of $160). Flying from Pittsburgh to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Pittsburgh to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$97Average$321FlexibilityNo cancel feeOn-time63%

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