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$49+ Cheap flights from Pennsylvania 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — MDW
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheap flight deals from Pennsylvania to Midway

Keep the following information in mind while searching for Pennsylvania to Midway flight deals. Data was last updated August 20, 2025.

Round-trip from

$92
(Southwest)

One-way from

$49
(Southwest)

Popular in

March

Cheapest in

September

Average price

$194

Good round-trip deal

$170 or less

Good one-way deal

$109 or less
From Pennsylvania to Chicago Midway
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One-way flight from Pennsylvania to Chicago Midway
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Highest demand for flights based on searches. 20% potential increase in price ($62 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 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 Pennsylvania to Chicago Midway.
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Price to beat on a one-way flight from Pennsylvania to Chicago Midway.
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Find flight deals from Pennsylvania to Midway

Cheapest flights from Pennsylvania to Midway
Explore the most affordable flight options available from Pennsylvania to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2025.

This Southwest deal was found by Cheapflights users on 8/19. 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 9/116:25 amPIT - MDW
Nonstop1h 25mSouthwest
Mon 9/159:30 amMDW - PIT
2 stops7h 35mSouthwest
Deal found 8/19$92
This Southwest deal was found by Cheapflights users on 8/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/96:20 amPIT - MDW
Nonstop1h 30mSouthwest
Mon 10/138:05 amMDW - PIT
1 stop8h 10mSouthwest
Deal found 8/20$93
This Southwest deal was found by Cheapflights users on 8/18. 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 10/111:05 amPIT - MDW
Nonstop1h 25mSouthwest
Mon 10/61:30 pmMDW - PIT
Nonstop1h 20mSouthwest
Deal found 8/18$97
This Southwest deal was found by Cheapflights users on 8/19. 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 10/2512:00 pmPIT - MDW
2 stops7h 35mSouthwest
Thu 10/302:15 pmMDW - PIT
2 stops8h 20mSouthwest
Deal found 8/19$107
This Southwest deal was found by Cheapflights users on 8/18. 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.
Sat 9/136:55 amPIT - MDW
Nonstop1h 25mSouthwest
Mon 9/151:15 pmMDW - PIT
Nonstop1h 25mSouthwest
Deal found 8/18$117
This Cheapflightsfares deal was found by Cheapflights users on 8/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/116:00 amPHL - MDW
Nonstop2h 11mFrontier
Sun 9/148:06 amMDW - PHL
Nonstop2h 01mFrontier
Deal found 8/19$127
This Frontier deal was found by Cheapflights users on 8/19. 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 9/126:00 amPHL - MDW
Nonstop2h 11mFrontier
Mon 9/228:15 amMDW - PHL
Nonstop2h 01mFrontier
Deal found 8/19$128
This FlightHub deal was found by Cheapflights users on 8/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/55:01 amPHL - MDW
1 stop8h 43mFrontier
Sun 10/128:25 amMDW - PHL
Nonstop2h 02mFrontier
Deal found 8/19$129
This Frontier deal was found by Cheapflights users on 8/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2512:00 pmPHL - MDW
Nonstop2h 10mFrontier
Thu 9/114:56 pmMDW - PHL
1 stop7h 01mFrontier
Deal found 8/18$130
This Cheapflightsfares deal was found by Cheapflights users on 8/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/46:00 amPHL - MDW
Nonstop2h 11mFrontier
Sun 9/148:06 amMDW - PHL
Nonstop2h 01mFrontier
Deal found 8/18$131
This Mytrip deal was found by Cheapflights users on 8/19. 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.
Sun 8/311:28 pmPHL - MDW
Nonstop2h 13mFrontier
Sun 9/710:13 amMDW - PHL
1 stop20h 22mFrontier
Deal found 8/19$132
This Frontier deal was found by Cheapflights users on 8/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/46:37 pmPHL - MDW
1 stop5h 40mFrontier
Fri 10/1012:13 pmMDW - PHL
Nonstop2h 00mFrontier
Deal found 8/18$133

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pennsylvania 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 20, 2025.
Use the filters below to find and compare flights from Pennsylvania to Chicago Midway Airport that are best for you.

Fly from

Pennsylvania

Fly to

Midway

Route

Depart

Return

Price

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Mon 1/5

1:10 pm-8:35 pm

2 stops8h 25m

Chicago Midway

Wed 1/7

10:15 am-12:40 pm

Nonstop1h 25m

$92

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 9/20

6:05 am-1:30 pm

2 stops8h 25m

Chicago Midway

Mon 9/22

9:30 am-11:55 am

Nonstop1h 25m

$92

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 9/24

6:40 pm-7:05 pm

Nonstop1h 25m

Chicago Midway

Thu 9/25

11:10 am-6:05 pm

2 stops5h 55m

$92

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 9/11

7:00 pm-7:25 pm

Nonstop1h 25m

Chicago Midway

Mon 9/15

9:30 am-6:05 pm

2 stops7h 35m

$92

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 9/9

12:05 pm-7:20 pm

2 stops8h 15m

Chicago Midway

Wed 9/10

8:20 pm-10:45 pm

Nonstop1h 25m

$92

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 11/8

12:15 pm-6:55 pm

2 stops7h 40m

Chicago Midway

Tue 11/11

10:15 am-12:45 pm

Nonstop1h 30m

$92

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 11/5

10:45 am-5:35 pm

2 stops7h 50m

Chicago Midway

Tue 11/11

10:15 am-12:45 pm

Nonstop1h 30m

$92

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 9/23

6:00 am-12:10 pm

2 stops7h 10m

Chicago Midway

Sat 9/27

9:50 am-12:15 pm

Nonstop1h 25m

$92

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 9/16

6:40 pm-7:05 pm

Nonstop1h 25m

Chicago Midway

Tue 9/23

1:00 pm-9:55 pm

2 stops7h 55m

$92

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 9/30

12:05 pm-5:45 pm

2 stops6h 40m

Chicago Midway

Thu 10/2

1:30 pm-3:50 pm

Nonstop1h 20m

$92

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 60 results
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Best time to book a flight from Pennsylvania to Midway

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

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

Currently, April is the cheapest month in which you can book a flight from Pennsylvania to Chicago Midway Airport (average of $160). Flying from Pennsylvania 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 PA to MDW?

Find hourly flight availability from Pennsylvania 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 20, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Pennsylvania to Chicago Midway Airport as you normally would.

Related info for your journey

Find useful and relevant information for your journey from Pennsylvania to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    For as low as $128, Southwest can have you in Chicago Midway Airport from Pennsylvania in 2h 11m. The distance between Pennsylvania and Chicago Midway Airport is about 666 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Pennsylvania to Chicago Midway Airport?

    The most popular flight routes from Pennsylvania to Chicago Midway Airport are New York John F Kennedy Intl - Chicago Midway, Newark - Chicago Midway and Washington, D.C. Dulles Intl - Chicago Midway.

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

    Looking for the cheapest flight from Pennsylvania to Chicago Midway Airport? While on average our users pay $247, our data indicates the cheapest price to be $78. The most popular route (New York John F Kennedy Intl - Chicago Midway), is priced around $147.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Pennsylvania to Chicago Midway Airport (average of $160). Flying from Pennsylvania 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 Pennsylvania to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Seattle to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
San Francisco to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Denver to O'Hare Intl flights
Baltimore to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Atlanta to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Ontario to O'Hare Intl flights
Newark to Midway flights
Boston to O'Hare Intl flights
Austin to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Baltimore to Midway flights
Los Angeles to Midway flights
Dulles Intl to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Atlanta to Midway flights
Hobby to Midway flights
Orlando to O'Hare Intl flights
San Francisco to Midway flights
LaGuardia to Midway flights
Hobby to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Burbank to O'Hare Intl flights
Portland to O'Hare Intl flights
Philadelphia to Midway flights
George Bush Intcntl to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Reagan-National to Midway flights
Nashville to O'Hare Intl flights
Denver to Midway flights
Orlando to Midway flights
Minneapolis to Midway flights
San Jose to O'Hare Intl flights
Tampa to O'Hare Intl flights
San Diego to O'Hare Intl flights
Miami to O'Hare Intl flights
Austin to Midway flights
Love Field to O'Hare Intl flights

Top 4 airlines flying from Pennsylvania to Midway

Discover the top 4 airlines that operate flights from Pennsylvania 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 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$60Average$157FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$124Average$303FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$144Average$359FlexibilityNo cancel feeOn-time69%
DeltaCheapest$228Average$442FlexibilityNo cancel feeOn-timeN/A

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