HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 4/23. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — MDW
Mar 30 — Apr 61
Sun 3/30
Sun 4/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Pittsburgh to Midway 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 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 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$137
(Southwest)

One-way from

$49
(Southwest)

Popular in

August

Cheapest in

April

Average price

$301

Good round-trip deal

$325 or less

Good one-way deal

$184 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. 6% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2025
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

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 March 25, 2025.

This Southwest deal was found by Cheapflights users on 3/24. 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 4/234:25 pmPIT - MDW
1 stop4h 25mSouthwest
Fri 4/252:40 pmMDW - PIT
2 stops6h 25mSouthwest
Deal found 3/24$137
This Delta deal was found by Cheapflights users on 3/24. 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 4/246:25 amPIT - MDW
1 stop3h 15mDelta
Fri 4/255:59 pmMDW - PIT
1 stop4h 04mDelta
Deal found 3/24$177
This CheapOair deal was found by Cheapflights users on 3/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/12:23 pmPIT - MDW
1 stop6h 28mFrontier
Thu 4/312:46 pmMDW - PIT
1 stop18h 57mFrontier
Deal found 3/25$200
This Mytrip deal was found by Cheapflights users on 3/24. 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.
Wed 4/911:00 amPIT - MDW
1 stop27h 29mAllegiant Air
Mon 5/128:35 amMDW - PIT
1 stop9h 52mAllegiant Air
Deal found 3/24$290

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 25, 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

Wed 4/23

4:25 pm-7:50 pm

1 stop4h 25m

Chicago Midway

Fri 4/25

2:40 pm-10:05 pm

2 stops6h 25m

$137

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 4/24

6:25 am-8:40 am

1 stop3h 15m

Chicago Midway

Fri 4/25

5:59 pm-11:03 pm

1 stop4h 04m

$177

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 4/1

2:23 pm-7:51 pm

1 stop6h 28m

Chicago Midway

Thu 4/3

12:46 pm-8:43 am

1 stop18h 57m

$200

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 4/9

11:00 am-1:29 pm

1 stop27h 29m

Chicago Midway

Mon 5/12

8:35 am-7:27 pm

1 stop9h 52m

$290

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 4/23

6:45 am-7:15 am

Nonstop1h 30m

$49

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 4/22

6:25 am-8:40 am

1 stop3h 15m

$89

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 4/9

11:48 am-7:35 pm

1 stop8h 47m

$100

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sun 6/22

8:19 pm-9:44 am

2 stops14h 25m

$153

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 5/29

12:31 pm-6:10 pm

3 stops30h 39m

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

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
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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, 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 March 25, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 10% 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 March 16, 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. Tuesday afternoons 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 March 25, 2025.
Read through reviews of airlines operating flights from Pittsburgh to Chicago, 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
4,272 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,890 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
730 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,273 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $137, 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 52% 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 $100 one-way.

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

    On average you can expect to pay $343 for a flight from Pittsburgh to Chicago Midway Airport. The cheapest flight overall is $93 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 Pittsburgh?

Book flights to Pittsburgh if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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 Pittsburgh to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Newark to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to Midway flights
Dulles Intl to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Philadelphia to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
LaGuardia to Midway flights
Dulles Intl to Midway flights
Philadelphia to Midway flights
Reagan-National to Midway flights
Pittsburgh to O'Hare Intl flights
Allentown to O'Hare Intl flights
Harrisburg to O'Hare Intl flights
Scranton to O'Hare Intl flights
Allentown to Midway flights
State College to O'Hare Intl flights
Harrisburg to Midway flights
Elmira to O'Hare Intl flights
Elmira to Midway flights
Newark to Rockford flights
Philadelphia to Rockford flights
Pittsburgh to Rockford flights
Latrobe to O'Hare Intl flights
Erie to O'Hare Intl flights
Williamsport to O'Hare Intl flights
State College to Midway flights
Erie to Midway flights
Scranton to Midway flights

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 March 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$132Average$302FlexibilityNo cancel feeOn-time63%
DeltaCheapest$197Average$463FlexibilityNo cancel feeOn-timeN/A
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.