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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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PHL
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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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 November 3, 2025.

This CheapOair deal was found by Cheapflights users on 11/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/151:37 pmMDW - PHL
1 stop9h 36mFrontier
Wed 11/196:50 pmPHL - MDW
1 stop22h 40mFrontier
Deal found 11/1$110
This Priceline deal was found by Cheapflights users on 11/1. 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.
Sat 11/151:37 pmMDW - LGA
1 stop8h 50mFrontier
Tue 11/186:24 amLGA - MDW
1 stop6h 14mFrontier
Deal found 11/1$110
This Priceline deal was found by Cheapflights users on 11/2. 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.
Mon 11/171:37 pmMDW - JFK
1 stop9h 56mFrontier
Thu 11/207:00 amJFK - MDW
1 stop10h 30mFrontier
Deal found 11/2$110
This Frontier deal was found by Cheapflights users on 11/2. 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.
Thu 12/46:15 amMDW - PHL
1 stop8h 44mFrontier
Thu 12/1111:07 amPHL - MDW
1 stop11h 46mFrontier
Deal found 11/2$111
This Booking.com deal was found by Cheapflights users on 11/2. 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.
Wed 11/191:56 pmMDW - LGA
1 stop8h 31mFrontier
Thu 11/2010:00 pmLGA - MDW
1 stop14h 17mFrontier
Deal found 11/2$111
This Booking.com deal was found by Cheapflights users on 11/3. 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.
Wed 12/102:49 pmMDW - JFK
1 stop9h 10mFrontier
Sat 12/134:29 pmJFK - MDW
1 stop19h 39mFrontier
Deal found 11/3$111
This Booking.com deal was found by Cheapflights users on 10/31. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/151:37 pmMDW - LGA
1 stop8h 50mFrontier
Mon 11/1712:30 pmLGA - MDW
1 stop10h 41mFrontier
Deal found 10/31$112
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Fri 11/218:41 pmMDW - PHL
Nonstop1h 57mFrontier
Mon 11/244:50 pmPHL - MDW
Nonstop2h 16mFrontier
Deal found 11/2$117
This CheapOair deal was found by Cheapflights users on 11/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/168:32 amMDW - PHL
Nonstop2h 02mFrontier
Wed 11/196:50 pmPHL - MDW
1 stop22h 40mFrontier
Deal found 11/2$119
This Mytrip deal was found by Cheapflights users on 11/3. 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.
Thu 12/117:44 amMDW - EWR
Nonstop2h 01mFrontier
Mon 12/1510:30 pmEWR - MDW
1 stop11h 16mFrontier
Deal found 11/3$121
This Trip.com deal was found by Cheapflights users on 11/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/92:49 pmMDW - LGA
1 stop7h 16mFrontier
Thu 12/116:20 amLGA - MDW
1 stop12h 48mFrontier
Deal found 11/2$123
This Trip.com deal was found by Cheapflights users on 11/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/92:49 pmMDW - JFK
1 stop9h 10mFrontier
Thu 12/111:00 pmJFK - MDW
1 stop6h 08mFrontier
Deal found 11/2$123

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 November 3, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$110
(CheapOair)

One-way from

$49
(Southwest)

Popular in

March

Cheapest in

October

Average price

$227

Good round-trip deal

$123 or less

Good one-way deal

$48 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. 17% potential increase in price ($57 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 November 2025
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.
Search Deals

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 November 3, 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

Wed 1/28

10:15 am-12:40 pm

Nonstop1h 25m

Pittsburgh

Wed 2/4

12:15 pm-12:45 pm

Nonstop1h 30m

$117

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 1/24

9:45 am-12:40 pm

Nonstop1h 55m

Philadelphia

Sat 1/31

5:50 am-7:05 am

Nonstop2h 15m

$139

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 1/29

5:55 pm-9:00 pm

Nonstop2h 05m

New York LaGuardia

Mon 2/2

9:45 pm-11:15 pm

Nonstop2h 30m

$139

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 1/8

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Mon 1/12

6:00 am-7:40 am

Nonstop2h 40m

$139

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 12/9

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Fri 12/12

9:55 pm-11:20 pm

Nonstop2h 25m

$143

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 1/30

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Mon 2/2

9:45 pm-11:15 pm

Nonstop2h 30m

$148

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 11/11

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Thu 11/13

7:15 am-8:45 am

Nonstop2h 30m

$149

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 11/20

6:00 am-9:00 am

Nonstop2h 00m

New York LaGuardia

Sun 11/23

7:15 am-8:45 am

Nonstop2h 30m

$149

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Sat 1/17

5:00 pm-11:46 pm

1 stop5h 46m

Pittsburgh

Sun 1/18

6:00 am-10:34 am

1 stop5h 34m

$157

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Fri 12/5

6:05 pm-9:00 pm

Nonstop1h 55m

Philadelphia

Sat 12/6

6:20 am-7:30 am

Nonstop2h 10m

$158

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

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 November 3, 2025.

It’s typically best to fly out from Chicago Midway Airport to Pennsylvania in the evening. Doing so could potentially save you 35% on the flight price compared to flying in the morning, 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 16, 2024.

Travelers seeking maximum savings on their Chicago Midway Airport to Pennsylvania flight should consider departing on Friday at noon when fares are most often at their lowest. Sunday afternoons 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 November 3, 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
4,238 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,117 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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, Delta, and Frontier can get you from Chicago Midway Airport to Pennsylvania in just under 1h 25m. Your travel time can differ by up to 4h 21m. 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 $61 while deals on Delta start at $89 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 $172, our data shows the cheapest flight currently is $53. When looking at the most popular route, (Chicago Midway - Newark), you can expect to pay $68 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.

See more FAQs

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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 John F Kennedy Intl flights
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Midway to Denver flights
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Midway to Miami flights
Midway to Tampa flights
O'Hare Intl to Minneapolis flights
Midway to Fort Lauderdale flights
O'Hare Intl to Palm Springs flights
O'Hare Intl to Charlotte flights
Midway to Hobby flights
Midway to Baltimore 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$68Average$159FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$103Average$300FlexibilityNo cancel feeOn-time63%

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