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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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PHL
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
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 April 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$137
(Southwest)

One-way from

$49
(Southwest)

Popular in

March

Cheapest in

August

Average price

$265

Good round-trip deal

$158 or less

Good one-way deal

$79 or less
Provider with most accurate pricing for Chicago (CHI)-Philadelphia flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Philadelphia flights.
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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. 32% potential increase in price ($102 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 15, 2025.

This Southwest deal was found by Cheapflights users on 4/15. 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 5/201:25 pmMDW - PIT
2 stops7h 35mSouthwest
Wed 5/214:00 pmPIT - MDW
1 stop4h 40mSouthwest
Deal found 4/15$122
This Southwest deal was found by Cheapflights users on 4/14. 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 5/246:15 pmMDW - LGA
Nonstop2h 10mSouthwest
Tue 5/276:10 amLGA - MDW
Nonstop2h 20mSouthwest
Deal found 4/14$137
This Cheapflightsfares deal was found by Cheapflights users on 4/15. 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 5/1612:15 pmMDW - PHL
Nonstop2h 02mFrontier
Mon 5/194:12 pmPHL - MDW
Nonstop2h 16mFrontier
Deal found 4/15$162
This Delta deal was found by Cheapflights users on 4/13. 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 5/175:25 pmMDW - EWR
1 stop4h 04mDelta
Sun 5/256:05 amEWR - MDW
1 stop8h 10mDelta
Deal found 4/13$168
This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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.
Tue 5/139:34 amMDW - LGA
1 stop5h 55mFrontier
Wed 5/146:30 amLGA - MDW
1 stop5h 56mFrontier
Deal found 4/14$176
This Delta deal was found by Cheapflights users on 4/14. 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 5/291:08 pmMDW - PIT
1 stop4h 35mDelta
Thu 6/56:25 amPIT - MDW
1 stop3h 15mDelta
Deal found 4/14$177
This Frontier deal was found by Cheapflights users on 4/14. 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.
Tue 5/139:34 amMDW - EWR
1 stop10h 32mFrontier
Sat 5/2411:00 amEWR - MDW
1 stop12h 02mFrontier
Deal found 4/14$178
This Frontier deal was found by Cheapflights users on 4/14. 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.
Wed 4/304:28 pmMDW - JFK
1 stop7h 05mFrontier
Wed 5/76:00 amJFK - MDW
1 stop6h 26mFrontier
Deal found 4/14$178
This Frontier deal was found by Cheapflights users on 4/14. 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.
Tue 4/1510:13 amMDW - IAD
1 stop8h 31mFrontier
Wed 4/1612:53 pmIAD - MDW
1 stop9h 40mFrontier
Deal found 4/14$178
This Southwest deal was found by Cheapflights users on 4/14. 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 5/283:20 pmMDW - DCA
Nonstop1h 50mSouthwest
Wed 5/288:55 pmDCA - MDW
Nonstop2h 00mSouthwest
Deal found 4/14$179
This Frontier deal was found by Cheapflights users on 4/14. 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.
Tue 4/156:45 amMDW - DCA
1 stop14h 14mFrontier
Thu 4/171:03 pmDCA - MDW
1 stop12h 18mFrontier
Deal found 4/14$188
This Southwest deal was found by Cheapflights users on 4/15. 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.
Sun 5/115:50 pmMDW - PHL
1 stop4h 55mSouthwest
Mon 5/195:50 amPHL - MDW
Nonstop2h 05mSouthwest
Deal found 4/15$189

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 April 15, 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

Tue 5/20

1:25 pm-10:00 pm

2 stops7h 35m

Pittsburgh

Wed 5/21

4:00 pm-7:40 pm

1 stop4h 40m

$122

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 5/24

6:15 pm-9:25 pm

Nonstop2h 10m

New York LaGuardia

Tue 5/27

6:10 am-7:30 am

Nonstop2h 20m

$137

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Fri 5/16

12:15 pm-3:17 pm

Nonstop2h 02m

Philadelphia

Mon 5/19

4:12 pm-5:28 pm

Nonstop2h 16m

$162

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 5/17

5:25 pm-10:29 pm

1 stop4h 04m

Newark

Sun 5/25

6:05 am-1:15 pm

1 stop8h 10m

$168

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 5/13

9:34 am-4:29 pm

1 stop5h 55m

New York LaGuardia

Wed 5/14

6:30 am-11:26 am

1 stop5h 56m

$176

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Thu 5/29

4:15 pm-12:21 am

1 stop7h 06m

Pittsburgh

Thu 6/5

6:25 am-8:40 am

1 stop3h 15m

$177

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Tue 5/13

9:34 am-9:06 pm

1 stop10h 32m

Newark

Sat 5/24

11:00 am-10:02 pm

1 stop12h 02m

$178

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Wed 4/30

4:28 pm-12:33 am

1 stop7h 05m

New York John F Kennedy Intl

Wed 5/7

6:00 am-11:26 am

1 stop6h 26m

$178

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Wed 5/28

3:20 pm-6:10 pm

Nonstop1h 50m

Washington, D.C. Reagan-National

Wed 5/28

8:55 pm-9:55 pm

Nonstop2h 00m

$179

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 5/1

8:30 am-2:23 pm

1 stop4h 53m

Washington, D.C. Dulles Intl

Sun 5/4

3:32 pm-11:54 pm

1 stop9h 22m

$180

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

Showing 1-10 of 58 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 April 15, 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.

Rainfall in Pennsylvania by month

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

In terms of precipitation, rainfall in Pennsylvania ranges from 2.7 - 4.4 inches per month. July is typically the wettest month, when rainfall can reach 4.4 in. February is typically the driest time to visit Pennsylvania when rainfall is around 2.7 in.

Temperature in Pennsylvania by month

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

If weather is an important factor for your trip to Pennsylvania, 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 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 33.8 F).

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 April 15, 2025.
Read through reviews of airlines operating flights from Chicago to Pennsylvania, such as Southwest, Delta and Allegiant Air. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,279 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Boarding

8.2

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
4,279 reviews
Southwest
8.0
Very good
4,279 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Boarding

8.2

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
7,917 reviews
Southwest
8.0
Very good
4,279 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Boarding

8.2

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
734 reviews
Southwest
8.0
Very good
4,279 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Boarding

8.2

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
3,281 reviews
Southwest
8.0
Very good
4,279 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Boarding

8.2

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 Midway to Pennsylvania. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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. Delta flights start at $79 while deals on Frontier start at $86 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 John F Kennedy Intl or Chicago Midway - New York LaGuardia.

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

    While on average a flight from Chicago Midway Airport to Pennsylvania is generally $188, our data shows the cheapest flight currently is $58. When looking at the most popular route, (Chicago Midway - Newark), you can expect to pay $168 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.
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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 April 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$117FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$103Average$301FlexibilityNo cancel feeOn-time63%

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