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$49+ Cheap flights from Midway (MDW) to Pennsylvania

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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PHL
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheap flight deals from Midway to Pennsylvania

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

Round-trip from

$93
(Southwest)

One-way from

$49
(Southwest)

Popular in

March

Cheapest in

September

Average price

$175

Good round-trip deal

$91 or less

Good one-way deal

$45 or less
From Chicago Midway to Pennsylvania
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One-way flight from Chicago Midway to Pennsylvania
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Highest demand for flights based on searches. 24% potential increase in price ($80 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 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 Chicago Midway to Pennsylvania.
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Price to beat on a one-way flight from Chicago Midway to Pennsylvania.
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Find flight deals from Midway to Pennsylvania

Cheapest flights from Midway to Pennsylvania
Explore the most affordable flight options available from Midway to Pennsylvania. 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 8/18. 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 10/239:55 pmMDW - PIT
Nonstop1h 20mSouthwest
Mon 10/279:20 pmPIT - MDW
1 stop12h 50mSouthwest
Deal found 8/18$93
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 9/187:15 amMDW - PIT
1 stop3h 55mSouthwest
Mon 9/225:00 pmPIT - MDW
1 stop3h 50mSouthwest
Deal found 8/19$97
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.
Tue 9/910:30 amMDW - PIT
2 stops6h 15mSouthwest
Tue 9/97:30 pmPIT - MDW
1 stop3h 55mSouthwest
Deal found 8/20$102
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 10/19:55 amMDW - PIT
Nonstop1h 25mSouthwest
Mon 10/64:35 pmPIT - MDW
1 stop7h 50mSouthwest
Deal found 8/18$107
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.
Mon 10/138:05 amMDW - PIT
1 stop8h 10mSouthwest
Wed 10/155:50 amPIT - MDW
2 stops7h 15mSouthwest
Deal found 8/19$108
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.
Tue 9/97:05 pmMDW - LGA
Nonstop2h 10mSouthwest
Wed 9/109:35 pmLGA - MDW
Nonstop2h 20mSouthwest
Deal found 8/19$127
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/28:15 amMDW - PHL
Nonstop2h 01mFrontier
Sat 10/46:37 pmPHL - MDW
1 stop5h 40mFrontier
Deal found 8/20$131
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/98:25 amMDW - PHL
Nonstop2h 02mFrontier
Mon 10/135:30 amPHL - MDW
1 stop10h 54mFrontier
Deal found 8/19$132
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/168:25 amMDW - PHL
Nonstop2h 02mFrontier
Mon 10/205:30 amPHL - MDW
1 stop11h 39mFrontier
Deal found 8/19$133
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/282:05 pmMDW - PHL
Nonstop2h 10mFrontier
Tue 9/26:37 pmPHL - MDW
1 stop20h 24mFrontier
Deal found 8/18$137
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.
Fri 8/292:05 pmMDW - PHL
Nonstop2h 10mFrontier
Fri 9/56:00 amPHL - MDW
Nonstop2h 11mFrontier
Deal found 8/19$138
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.
Wed 10/11:05 pmMDW - PIT
Nonstop1h 25mSouthwest
Sun 10/56:35 amPIT - MDW
Nonstop1h 25mSouthwest
Deal found 8/19$138

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Pennsylvania 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 Chicago Midway Airport to Pennsylvania that are best for you.

Fly from

Midway

Fly to

Pennsylvania

Route

Depart

Return

Price

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Thu 10/23

9:55 pm-12:15 am

Nonstop1h 20m

Pittsburgh

Mon 10/27

9:20 pm-9:10 am

1 stop12h 50m

$93

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Sat 10/4

6:00 am-12:00 pm

1 stop5h 00m

Pittsburgh

Sat 10/4

1:30 pm-7:05 pm

1 stop6h 35m

$97

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Thu 9/18

6:30 am-11:00 am

1 stop3h 30m

Pittsburgh

Mon 9/22

5:00 pm-7:50 pm

1 stop3h 50m

$97

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Wed 9/24

9:00 am-4:35 pm

1 stop6h 35m

Pittsburgh

Thu 9/25

6:50 pm-10:50 pm

1 stop5h 00m

$97

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Wed 10/1

9:55 am-12:20 pm

Nonstop1h 25m

Pittsburgh

Mon 10/6

9:55 am-10:20 am

Nonstop1h 25m

$97

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Wed 9/10

10:30 am-5:45 pm

2 stops6h 15m

Pittsburgh

Wed 9/10

7:30 pm-10:25 pm

1 stop3h 55m

$102

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Tue 9/16

10:30 am-5:45 pm

2 stops6h 15m

Pittsburgh

Wed 9/17

1:10 pm-5:05 pm

1 stop4h 55m

$102

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Tue 9/9

10:30 am-5:45 pm

2 stops6h 15m

Pittsburgh

Tue 9/9

7:30 pm-10:25 pm

1 stop3h 55m

$102

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Mon 9/29

8:15 pm-11:25 pm

Nonstop2h 10m

New York LaGuardia

Fri 10/3

9:35 pm-11:05 pm

Nonstop2h 30m

$127

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 9/16

6:00 am-9:00 am

Nonstop2h 00m

New York LaGuardia

Tue 9/23

9:00 am-10:25 am

Nonstop2h 25m

$127

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

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

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

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

Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Pennsylvania (average of $236). Flying from Chicago Midway Airport to Pennsylvania in March is currently the most expensive (average of $295). 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 MDW to PA?

Find hourly flight availability from Midway to Pennsylvania. 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 Chicago Midway Airport to Pennsylvania as you normally would.

Reviews of airlines servicing Pennsylvania

Get insights into the airlines that provide service to Pennsylvania. 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 Pennsylvania. Reviews last updated August 20, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Pennsylvania, such as Southwest and Frontier. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,207 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Midway to Pennsylvania. 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 Chicago Midway Airport to Pennsylvania?

    Southwest, Frontier, and Delta can get you from Chicago Midway Airport to Pennsylvania in just under 1h 20m. Your travel time can differ by up to 2h 27m. The distance between Chicago Midway Airport and Pennsylvania is about 400 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $49. Frontier flights start at $73 while deals on Delta start at $84 one-way.

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

    The most popular route from Chicago Midway Airport to Pennsylvania is Chicago Midway - Newark. You may also consider Chicago Midway - New York LaGuardia or Chicago Midway - New York John F Kennedy Intl.

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

    While on average a flight from Chicago Midway Airport to Pennsylvania is generally $206, our data shows the cheapest flight currently is $61. When looking at the most popular route, (Chicago Midway - Newark), you can expect to pay $98 for that flight.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Pennsylvania (average of $236). Flying from Chicago Midway Airport to Pennsylvania in March is currently the most expensive (average of $295). 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.

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Alternative routes for Midway to Pennsylvania

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to LaGuardia flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to John F Kennedy Intl flights
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O'Hare Intl to Los Angeles flights
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O'Hare Intl to San Francisco flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Boston flights
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Midway to Las Vegas flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Reagan-National flights
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Midway to Newark flights
O'Hare Intl to Honolulu flights
Midway to LaGuardia flights
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O'Hare Intl to Santa Ana flights
Midway to John F Kennedy Intl flights
O'Hare Intl to Austin flights
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Midway to Atlanta flights
Midway to Denver flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to Hobby flights
O'Hare Intl to Salt Lake City flights
Midway to Orlando flights
Midway to Sky Harbor Intl flights
Midway to Miami flights
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O'Hare Intl to Cleveland flights
Midway to Tampa flights
O'Hare Intl to Charleston flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Charlotte flights
O'Hare Intl to Minneapolis flights
Midway to Dulles Intl flights
Midway to San Francisco flights

Top 2 airlines flying from Midway to Pennsylvania

Discover the top 2 airlines that operate flights from Midway to Pennsylvania. 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$67Average$155FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$116Average$355FlexibilityNo cancel feeOn-time63%

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