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$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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — MDW
Aug 6 — Aug 131
Wed 8/6
Wed 8/13
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 August 1, 2025.

Round-trip from

$94
(Southwest)

One-way from

$49
(Southwest)

Popular in

June

Cheapest in

September

Average price

$270

Good round-trip deal

$171 or less

Good one-way deal

$104 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. 12% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 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 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 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.
Sat 8/236:55 amPIT - MDW
Nonstop1h 25mSouthwest
Mon 8/259:30 amMDW - PIT
Nonstop1h 25mSouthwest
Deal found 7/31$94
This Delta deal was found by Cheapflights users on 7/29. 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 9/66:20 amPIT - MDW
1 stop3h 15mDelta
Sat 9/66:17 pmMDW - PIT
1 stop4h 05mDelta
Deal found 7/29$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.
Fri 8/83:49 pmPIT - MDW
1 stop9h 02mFrontier
Sat 8/99:12 pmMDW - PIT
1 stop10h 59mFrontier
Deal found 7/30$188

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 August 1, 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

Sat 8/23

6:55 am-7:20 am

Nonstop1h 25m

Chicago Midway

Mon 8/25

1:15 pm-3:40 pm

Nonstop1h 25m

$94

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 9/6

6:20 am-8:35 am

1 stop3h 15m

Chicago Midway

Sat 9/6

6:17 pm-11:22 pm

1 stop4h 05m

$177

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Fri 8/8

3:49 pm-11:51 pm

1 stop9h 02m

Chicago Midway

Sat 8/9

9:12 pm-9:11 am

1 stop10h 59m

$188

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 8/28

4:15 pm-4:40 pm

Nonstop1h 25m

$49

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 8/27

10:25 am-12:28 pm

1 stop3h 03m

$89

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Mon 8/4

3:49 pm-11:51 pm

1 stop9h 02m

$105

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sun 10/12

8:45 am-4:50 pm

1 stop9h 05m

$113

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Fri 9/12

7:10 am-4:43 pm

2 stops10h 33m

$146

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

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 August 1, 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 July 27, 2025.

Travelers seeking maximum savings on their Pittsburgh to Chicago Midway Airport flight should consider departing on Thursday afternoons when fares are most often at their lowest. Tuesday afternoons 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 August 1, 2025.
Read through reviews of airlines operating flights from Pittsburgh to Chicago Midway Airport, such as Southwest, Delta, and Allegiant Air. Reviews also offer insight into each airline's 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.
Allegiant Air
7.2
Good
702 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 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.

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

    Southwest, at $94, was found to be the cheapest airline from Pittsburgh to Chicago Midway Airport.Alternate airlines to your destination round-trip include Delta and Frontier. Southwest is priced at 68% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Pittsburgh to Chicago Midway Airport one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $49. Delta flights start at $89 while deals on Frontier start at $105 one-way.

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

    On average you can expect to pay $240 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 $91.

  • 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
Valparaiso
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 August 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$126Average$313FlexibilityNo cancel feeOn-time63%

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