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$50+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PHL
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$100
(Frontier)

One-way from

$50
(Cheapflightsfares)

Popular in

February

Cheapest in

August

Average price

$361

Good round-trip deal

$219 or less

Good one-way deal

$108 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. 35% potential increase in price ($111 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Frontier deal was found by Cheapflights users on 2/20. 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.
Wed 4/234:28 pmMDW - LGA
1 stop5h 35mFrontier
Wed 5/76:30 amLGA - MDW
1 stop5h 56mFrontier
Deal found 2/20$100
This Frontier deal was found by Cheapflights users on 2/20. 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.
Tue 4/14:40 pmMDW - JFK
1 stop7h 03mFrontier
Tue 4/89:00 amJFK - MDW
1 stop11h 45mFrontier
Deal found 2/20$100
This Frontier deal was found by Cheapflights users on 2/19. 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.
Sat 5/310:48 amMDW - EWR
1 stop9h 18mFrontier
Mon 5/510:00 pmEWR - MDW
1 stop11h 19mFrontier
Deal found 2/19$104
This Southwest deal was found by Cheapflights users on 2/20. 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.
Sat 4/266:15 pmMDW - LGA
Nonstop2h 10mSouthwest
Tue 4/296:10 amLGA - MDW
Nonstop2h 20mSouthwest
Deal found 2/20$147
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/155:59 pmMDW - EWR
1 stop4h 00mDelta
Tue 4/2912:40 pmEWR - MDW
1 stop6h 40mDelta
Deal found 2/20$167
This Booking.com deal was found by Cheapflights users on 2/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1312:45 pmMDW - PIT
1 stop19h 31mFrontier
Sun 3/169:29 pmPIT - MDW
1 stop23h 06mFrontier
Deal found 2/20$170
This Frontier deal was found by Cheapflights users on 2/19. 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.
Tue 4/1511:00 amMDW - IAD
1 stop7h 44mFrontier
Mon 4/2112:58 pmIAD - MDW
1 stop7h 48mFrontier
Deal found 2/19$175
This Southwest deal was found by Cheapflights users on 2/19. 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 3/203:20 pmMDW - DCA
Nonstop1h 50mSouthwest
Mon 3/242:45 pmDCA - MDW
Nonstop2h 00mSouthwest
Deal found 2/19$177
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/75:05 pmMDW - PIT
1 stop6h 02mDelta
Wed 3/125:59 pmPIT - MDW
1 stop5h 24mDelta
Deal found 2/20$177
This Frontier deal was found by Cheapflights users on 2/20. 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.
Sat 4/126:45 amMDW - DCA
1 stop14h 14mFrontier
Tue 4/156:00 pmDCA - MDW
1 stop7h 21mFrontier
Deal found 2/20$178
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/66:00 amMDW - IAD
1 stop4h 57mDelta
Mon 3/106:00 amIAD - MDW
1 stop3h 45mDelta
Deal found 2/20$197
This Flightnetwork deal was found by Cheapflights users on 2/20. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/35:15 amMDW - PHL
1 stop19h 00mFrontier
Sun 4/611:57 amPHL - MDW
Nonstop2h 24mFrontier
Deal found 2/20$208

Find flights from Midway to Pennsylvania within your budget

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 February 20, 2025.

Fly from

Midway

Fly to

Pennsylvania

Route

Depart

Return

Price

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 4/23

4:28 pm-11:03 pm

1 stop5h 35m

New York LaGuardia

Thu 5/8

6:30 am-1:34 pm

1 stop8h 04m

$100

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Tue 4/1

4:40 pm-12:43 am

1 stop7h 03m

New York John F Kennedy Intl

Tue 4/8

9:00 am-7:45 pm

1 stop11h 45m

$100

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 5/3

10:48 am-9:06 pm

1 stop9h 18m

Newark

Mon 5/5

10:00 pm-8:19 am

1 stop11h 19m

$104

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 4/26

6:15 pm-9:25 pm

Nonstop2h 10m

New York LaGuardia

Tue 4/29

6:10 am-7:30 am

Nonstop2h 20m

$147

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Tue 4/15

5:59 pm-10:59 pm

1 stop4h 00m

Newark

Tue 4/29

12:40 pm-6:20 pm

1 stop6h 40m

$167

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Thu 3/13

12:45 pm-9:16 am

1 stop19h 31m

Pittsburgh

Sun 3/16

9:29 pm-7:35 pm

1 stop23h 06m

$170

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Tue 4/15

11:00 am-7:44 pm

1 stop7h 44m

Washington, D.C. Dulles Intl

Mon 4/21

12:58 pm-7:46 pm

1 stop7h 48m

$175

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Thu 3/20

3:20 pm-6:10 pm

Nonstop1h 50m

Washington, D.C. Reagan-National

Mon 3/24

2:45 pm-3:45 pm

Nonstop2h 00m

$177

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Fri 3/7

6:00 am-11:46 am

1 stop4h 46m

Pittsburgh

Thu 3/13

6:25 am-8:45 am

1 stop3h 20m

$177

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Sat 4/12

6:45 am-9:59 pm

1 stop14h 14m

Washington, D.C. Reagan-National

Tue 4/15

6:00 pm-12:21 am

1 stop7h 21m

$178

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 54 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.

Travel insights for flights from Midway to Pennsylvania

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

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 February 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.

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 February 20, 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
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Allegiant Air
7.3
Good
765 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Frontier
6.0
Okay
3,355 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Frontier, which is currently one of the cheapest options available, starting at $50. Southwest flights start at $59 while deals on Delta start at $87 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 $248, our data shows the cheapest flight currently is $64. When looking at the most popular route, (Chicago Midway - Newark), you can expect to pay $83 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$59Average$119FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$137Average$350FlexibilityNo cancel feeOn-time63%
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