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$55+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — MDW
Jan 27 — Feb 31
Mon 1/27
Mon 2/3
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 January 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$207
(Southwest)

One-way from

$55
(Frontier)

Popular in

May

Cheapest in

December

Average price

$326

Good round-trip deal

$351 or less

Good one-way deal

$212 or less
Provider with most accurate pricing for Pittsburgh-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Pittsburgh-Chicago Midway flights.
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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. 4% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 22, 2025.

This Delta deal was found by Cheapflights users on 1/21. 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.
Wed 4/236:05 pmPIT - MDW
1 stop5h 24mDelta
Mon 4/284:59 pmMDW - PIT
1 stop6h 14mDelta
Deal found 1/21$177
This Southwest deal was found by Cheapflights users on 1/21. 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 2/157:50 pmPIT - MDW
Nonstop1h 30mSouthwest
Mon 2/178:25 pmMDW - PIT
Nonstop1h 25mSouthwest
Deal found 1/21$201
This Frontier deal was found by Cheapflights users on 1/20. 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.
Thu 1/304:41 pmPIT - MDW
1 stop8h 36mFrontier
Sun 2/27:15 amMDW - PIT
1 stop7h 29mFrontier
Deal found 1/20$260
This Mytrip deal was found by Cheapflights users on 1/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/244:55 pmPIT - MDW
2 stops17h 46mAllegiant Air
Mon 7/288:03 amMDW - PIT
1 stop6h 09mAllegiant Air
Deal found 1/22$481

Find flights from Pittsburgh to Midway within your budget

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 January 22, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Fri 2/21

9:00 pm-12:15 am

1 stop4h 15m

Chicago Midway

Fri 2/28

8:25 pm-10:50 pm

Nonstop1h 25m

$207

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Mon 4/14

4:55 pm-10:29 pm

1 stop6h 34m

Chicago Midway

Wed 4/23

6:00 am-1:44 pm

1 stop6h 44m

$258

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Fri 3/14

10:06 am-7:35 pm

1 stop10h 29m

Chicago Midway

Sun 3/16

12:36 pm-8:46 am

1 stop19h 10m

$338

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 2/20

11:30 am-5:32 pm

1 stop7h 02m

Chicago Midway

Thu 2/27

6:20 pm-9:29 pm

3 stops26h 09m

$529

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 4/8

2:20 pm-7:51 pm

1 stop6h 31m

$55

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Mon 2/24

7:55 pm-8:25 pm

Nonstop1h 30m

$69

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 3/20

10:15 am-12:36 pm

1 stop3h 21m

$89

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sun 3/16

6:00 am-5:36 pm

1 stop12h 36m

$172

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 3/5

6:14 pm-5:36 pm

3 stops24h 22m

$196

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/22

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 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.

Travel insights for flights from Pittsburgh to Midway

Get recent, data-driven insights about flights from Pittsburgh to Midway including ideal travel times, pricing trends, and more.

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 January 22, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 21% 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 January 21, 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. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 January 22, 2025.
Read through reviews of airlines operating flights from Pittsburgh to Chicago, such as Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,654 reviews

Boarding

8.2

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,654 reviews
Southwest
8.1
Very good
4,654 reviews

Boarding

8.2

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,512 reviews
Southwest
8.1
Very good
4,654 reviews

Boarding

8.2

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,654 reviews

Boarding

8.2

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,441 reviews
Southwest
8.1
Very good
4,654 reviews

Boarding

8.2

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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. 2 airlines have 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 $207, 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 32% 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 Frontier, which is currently one of the cheapest options available, starting at $55. Southwest flights start at $69 while deals on Delta start at $94 one-way.

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

    On average you can expect to pay $357 for a flight from Pittsburgh to Chicago Midway Airport. The cheapest flight overall is $134 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, 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 Pittsburgh?

Book flights to Pittsburgh if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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 2 airlines flying from Pittsburgh to Midway

Discover the top 2 airlines 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 January 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$153Average$303FlexibilityNo cancel feeOn-time63%
DeltaCheapest$155Average$363FlexibilityNo cancel feeOn-timeN/A
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