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$46+ 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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PHL
jul. 8 — jul. 151
mar. 7/8
mar. 7/15
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 julio 3, 2025.

Round-trip from

$121
(Priceline)

One-way from

$46
(Southwest)

Popular in

March

Cheapest in

August

Average price

$177

Good round-trip deal

$155 or less

Good one-way deal

$94 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. 29% potential increase in price ($95 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 3, 2025.

This Priceline deal was found by Cheapflights users on 7/1. 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.
jue. 9/255:04 pmMDW - JFK
1 stop6h 38mFrontier
lun. 9/299:00 amJFK - MDW
1 stop7h 58mFrontier
Deal found 7/1$121
This Priceline deal was found by Cheapflights users on 7/2. 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.
vie. 9/125:04 pmMDW - LGA
1 stop5h 27mFrontier
lun. 9/156:30 amLGA - MDW
1 stop10h 28mFrontier
Deal found 7/2$122
This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/36:00 amMDW - LGA
Nonstop2h 00mSouthwest
mié. 9/39:35 pmLGA - MDW
Nonstop2h 20mSouthwest
Deal found 7/1$137
This Priceline deal was found by Cheapflights users on 7/1. 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.
jue. 9/45:04 pmMDW - EWR
1 stop6h 30mFrontier
dom. 9/711:15 amEWR - MDW
1 stop5h 43mFrontier
Deal found 7/1$145
This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/17:50 amMDW - PIT
Nonstop1h 25mSouthwest
mié. 8/612:05 pmPIT - MDW
2 stops8h 05mSouthwest
Deal found 7/1$146
This Priceline deal was found by Cheapflights users on 7/1. 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.
vie. 8/18:35 amMDW - PIT
1 stop9h 05mFrontier
lun. 8/43:49 pmPIT - MDW
1 stop9h 02mFrontier
Deal found 7/1$149
This Priceline deal was found by Cheapflights users on 7/1. 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.
sáb. 9/1310:51 amMDW - IAD
1 stop6h 21mFrontier
lun. 9/1510:12 amIAD - MDW
1 stop11h 40mFrontier
Deal found 7/1$150
This FlightHub deal was found by Cheapflights users on 7/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/256:40 pmMDW - PHL
Nonstop2h 05mFrontier
sáb. 7/265:30 amPHL - MDW
1 stop18h 05mFrontier
Deal found 7/2$157
This Southwest deal was found by Cheapflights users on 7/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/219:20 amMDW - DCA
Nonstop1h 50mSouthwest
lun. 8/259:00 pmDCA - MDW
Nonstop2h 00mSouthwest
Deal found 7/2$157
This Southwest deal was found by Cheapflights users on 7/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/26:30 amMDW - PHL
Nonstop1h 55mSouthwest
dom. 8/245:30 amPHL - MDW
Nonstop2h 00mSouthwest
Deal found 7/2$159
This Delta deal was found by Cheapflights users on 7/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/36:00 amMDW - EWR
1 stop5h 11mDelta
mié. 9/106:15 amEWR - MDW
1 stop7h 48mDelta
Deal found 7/3$167
This Delta deal was found by Cheapflights users on 7/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/169:31 amMDW - PIT
1 stop2h 49mDelta
mar. 8/1910:25 amPIT - MDW
1 stop3h 03mDelta
Deal found 7/2$177

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 julio 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

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

jue. 9/25

5:04 pm-12:42 am

1 stop6h 38m

New York John F Kennedy Intl

lun. 9/29

9:00 am-3:58 pm

1 stop7h 58m

$121

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

vie. 9/12

5:04 pm-11:31 pm

1 stop5h 27m

New York LaGuardia

lun. 9/15

6:30 am-3:58 pm

1 stop10h 28m

$122

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

mié. 9/3

6:00 am-9:00 am

Nonstop2h 00m

New York LaGuardia

mié. 9/3

9:35 pm-10:55 pm

Nonstop2h 20m

$137

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

jue. 9/4

5:04 pm-12:34 am

1 stop6h 30m

Newark

dom. 9/7

11:15 am-3:58 pm

1 stop5h 43m

$145

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

vie. 8/1

7:50 am-10:15 am

Nonstop1h 25m

Pittsburgh

mié. 8/6

12:05 pm-7:10 pm

2 stops8h 05m

$146

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

vie. 8/1

8:35 am-6:40 pm

1 stop9h 05m

Pittsburgh

lun. 8/4

3:49 pm-11:51 pm

1 stop9h 02m

$149

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

sáb. 9/13

10:51 am-6:12 pm

1 stop6h 21m

Washington, D.C. Dulles Intl

lun. 9/15

10:12 am-8:52 pm

1 stop11h 40m

$150

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

jue. 8/21

5:30 am-8:20 am

Nonstop1h 50m

Washington, D.C. Reagan-National

lun. 8/25

9:05 am-10:05 am

Nonstop2h 00m

$157

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

vie. 7/25

6:40 pm-9:45 pm

Nonstop2h 05m

Philadelphia

dom. 7/27

5:30 am-1:47 pm

1 stop9h 17m

$157

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

sáb. 8/2

6:30 am-9:25 am

Nonstop1h 55m

Philadelphia

mié. 8/6

6:50 pm-10:25 pm

1 stop4h 35m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 44 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 julio 3, 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 julio 3, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Pennsylvania, such as Southwest, Delta, and Allegiant Air. 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
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.3
Good
708 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,286 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $46. Frontier flights start at $67 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 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 $69. When looking at the most popular route, (Chicago Midway - Newark), you can expect to pay $105 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.

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.
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Midway to Atlanta flights
O'Hare Intl to Atlanta flights
Midway to John F Kennedy Intl flights
O'Hare Intl to Honolulu flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Portland flights
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Midway to Dallas/Fort Worth flights
Midway to LaGuardia flights
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Midway to Las Vegas flights
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Midway to Denver flights
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Midway to San Francisco flights
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O'Hare Intl to Fort Myers flights
Midway to Tampa flights
O'Hare Intl to Charlotte flights
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Midway to Minneapolis flights
Midway to Miami flights
Midway to Philadelphia flights
O'Hare Intl to Kalispell 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 julio 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$62Average$138FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$117Average$351FlexibilityNo cancel feeOn-time63%

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