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$61+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PHL
Jan 31 — Feb 71
Sat 1/31
Sat 2/7
1 adult, Economy
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Cheap 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 January 1, 2026.

This Southwest deal was found by Cheapflights users on 12/31. 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 12/317:15 pmMDW - LGA
Nonstop2h 05mSouthwest
Tue 1/62:30 pmLGA - MDW
Nonstop2h 40mSouthwest
Deal found 12/31$357
This Southwest deal was found by Cheapflights users on 12/31. 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 12/315:15 pmMDW - LGA
1 stop4h 55mSouthwest
Wed 1/72:30 pmLGA - MDW
Nonstop2h 40mSouthwest
Deal found 12/31$367
This Lucky2Go deal was found by Cheapflights users on 12/30. 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 Lucky2Go is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:15 amMDW - EWR
1 stop15h 50mFrontier
Wed 1/75:59 amEWR - MDW
1 stop17h 18mFrontier
Deal found 12/30$391
This Southwest deal was found by Cheapflights users on 12/29. 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 12/317:15 pmMDW - LGA
Nonstop2h 05mSouthwest
Mon 1/59:55 pmLGA - MDW
Nonstop2h 25mSouthwest
Deal found 12/29$392
This Southwest deal was found by Cheapflights users on 12/30. 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 12/315:55 pmMDW - LGA
Nonstop2h 05mSouthwest
Fri 1/29:00 amLGA - MDW
Nonstop2h 25mSouthwest
Deal found 12/30$447
This Kiwi.com deal was found by Cheapflights users on 12/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - EWR
2 stops15h 28mMultiple Airlines
Tue 1/610:05 pmEWR - MDW
1 stop25h 12mMultiple Airlines
Deal found 12/30$450
This Kiwi.com deal was found by Cheapflights users on 12/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - JFK
2 stops16h 29mFrontier
Wed 1/76:00 amJFK - MDW
1 stop9h 06mFrontier
Deal found 12/30$463
This Southwest deal was found by Cheapflights users on 12/30. 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 12/317:15 pmMDW - LGA
Nonstop2h 05mSouthwest
Sat 1/36:10 amLGA - MDW
Nonstop2h 25mSouthwest
Deal found 12/30$467
This Kiwi.com deal was found by Cheapflights users on 12/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - EWR
2 stops15h 28mMultiple Airlines
Mon 1/510:30 pmEWR - MDW
1 stop24h 47mMultiple Airlines
Deal found 12/30$470
This Kiwi.com deal was found by Cheapflights users on 12/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - EWR
2 stops15h 28mMultiple Airlines
Thu 1/85:59 amEWR - MDW
1 stop6h 32mMultiple Airlines
Deal found 12/30$472
This Kiwi.com deal was found by Cheapflights users on 12/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - PHL
2 stops26h 37mMultiple Airlines
Wed 1/75:17 amPHL - MDW
1 stop9h 49mMultiple Airlines
Deal found 12/30$473
This Southwest deal was found by Cheapflights users on 12/30. 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 12/317:15 pmMDW - LGA
Nonstop2h 05mSouthwest
Sun 1/47:25 amLGA - MDW
1 stop8h 55mSouthwest
Deal found 12/30$473

Find flight deals from Midway to Pennsylvania

Keep the following information in mind while searching for Midway to Pennsylvania flight deals. Data was last updated January 1, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$97
(Southwest)

One-way from

$61
(Kiwi.com)

Popular in

March

Cheapest in

October

Average price

$287

Good round-trip deal

$169 or less

Good one-way deal

$119 or less
Provider with most accurate pricing for Chicago (CHI)-Philadelphia flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Philadelphia flights.
Search Deals
From Chicago Midway to Pennsylvania
Search Deals
One-way flight from Chicago Midway to Pennsylvania
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($52 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Pennsylvania.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Pennsylvania.
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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 January 1, 2026.
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

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 1/20

5:55 pm-9:00 pm

Nonstop2h 05m

New York LaGuardia

Fri 1/23

9:45 pm-11:15 pm

Nonstop2h 30m

$97

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 2/7

5:35 pm-8:40 pm

Nonstop2h 05m

New York LaGuardia

Mon 2/9

6:30 pm-8:15 pm

Nonstop2h 45m

$97

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 2/3

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Wed 2/4

9:45 pm-11:15 pm

Nonstop2h 30m

$97

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Mon 2/23

6:05 pm-9:10 pm

Nonstop2h 05m

New York LaGuardia

Tue 2/24

6:00 am-7:40 am

Nonstop2h 40m

$117

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 1/14

5:55 pm-9:00 pm

Nonstop2h 05m

New York LaGuardia

Sun 1/18

2:30 pm-4:10 pm

Nonstop2h 40m

$117

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Thu 1/15

6:30 pm-9:30 pm

Nonstop2h 00m

Newark

Sun 1/18

11:30 am-10:19 pm

1 stop11h 49m

$122

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 1/14

5:55 pm-9:00 pm

Nonstop2h 05m

New York LaGuardia

Sat 1/17

8:00 am-9:30 am

Nonstop2h 30m

$137

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 2/21

6:00 am-5:56 pm

1 stop10h 56m

Philadelphia

Tue 2/24

11:40 am-7:07 pm

1 stop8h 27m

$145

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Thu 1/22

5:01 pm-1:08 am

1 stop7h 07m

Newark

Tue 1/27

6:00 am-12:05 pm

1 stop7h 05m

$145

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Tue 1/20

1:20 pm-9:35 pm

1 stop7h 15m

Newark

Tue 1/27

6:00 am-12:05 pm

1 stop7h 05m

$145

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/31

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, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Pennsylvania (average of $67). Flying from Chicago Midway Airport to Pennsylvania in June is currently the most expensive (average of $169). 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 January 1, 2026.

It’s typically best to fly out from Chicago Midway Airport to Pennsylvania in the morning. Doing so could potentially save you 8% on the flight price compared to flying in the evening, which is usually more expensive.

What is the cheapest day to fly from Chicago Midway Airport to Pennsylvania?

Use this chart to determine the cheapest time to fly round-trip from Midway to Pennsylvania. Price data was last updated on December 27, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Pennsylvania flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 January 1, 2026.
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
4,252 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,252 reviews
Southwest
8.0
Very good
4,252 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.7
Fair
3,066 reviews
Southwest
8.0
Very good
4,252 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 2h. Your travel time can differ by up to 1h 38m. The distance between Chicago Midway Airport and Pennsylvania is about 708 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 - New York John F Kennedy Intl. You may also consider Chicago Midway - New York LaGuardia or Chicago Midway - Newark.

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

    While on average a flight from Chicago Midway Airport to Pennsylvania is generally $266, our data shows the cheapest flight currently is $114. When looking at the most popular route, (Chicago Midway - New York John F Kennedy Intl), you can expect to pay $145 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, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Pennsylvania (average of $67). Flying from Chicago Midway Airport to Pennsylvania in June is currently the most expensive (average of $169). 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 January 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$67Average$158FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$103Average$297FlexibilityNo cancel feeOn-time63%

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