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Midway

$55+ Cheap flights from Pennsylvania to Midway (MDW)

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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — MDW
Jan 21 — Jan 281
Wed 1/21
Wed 1/28
1 adult, Economy
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Cheap flight deals from Pennsylvania to Midway

Cheapest flights from Pennsylvania to Midway
Explore the most affordable flight options available from Pennsylvania to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 22, 2025.

This Frontier deal was found by Cheapflights users on 12/21. 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.
Sun 12/2811:30 amEWR - MDW
Nonstop2h 31mFrontier
Thu 1/17:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/21$129
This Frontier deal was found by Cheapflights users on 12/22. 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 12/3011:30 amEWR - MDW
Nonstop2h 31mFrontier
Thu 1/17:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/22$165
This Frontier deal was found by Cheapflights users on 12/20. 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.
Sun 12/2811:30 amEWR - MDW
Nonstop2h 31mFrontier
Mon 1/58:15 amMDW - EWR
1 stop12h 20mFrontier
Deal found 12/20$171
This Frontier deal was found by Cheapflights users on 12/21. 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.
Sun 12/2811:30 amEWR - MDW
Nonstop2h 31mFrontier
Sun 1/47:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/21$178
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Sun 12/2811:30 amEWR - MDW
Nonstop2h 31mFrontier
Tue 12/307:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/21$186
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:30 amEWR - MDW
Nonstop2h 31mFrontier
Thu 1/17:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/20$192
This Southwest deal was found by Cheapflights users on 12/20. 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.
Wed 12/316:05 amLGA - MDW
Nonstop2h 30mSouthwest
Sat 1/35:50 amMDW - LGA
Nonstop2h 05mSouthwest
Deal found 12/20$200
This Frontier deal was found by Cheapflights users on 12/21. 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 12/315:15 amPHL - MDW
1 stop9h 06mFrontier
Mon 1/52:16 pmMDW - PHL
1 stop8h 27mFrontier
Deal found 12/21$213
This Southwest deal was found by Cheapflights users on 12/20. 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.
Mon 12/299:50 pmLGA - MDW
Nonstop2h 25mSouthwest
Thu 1/16:00 amMDW - LGA
Nonstop2h 00mSouthwest
Deal found 12/20$213
This Southwest deal was found by Cheapflights users on 12/20. 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.
Wed 12/316:55 pmDCA - MDW
Nonstop2h 05mSouthwest
Thu 1/17:30 amMDW - DCA
Nonstop1h 45mSouthwest
Deal found 12/20$223
This Southwest deal was found by Cheapflights users on 12/20. 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.
Sun 12/286:00 amLGA - MDW
Nonstop2h 30mSouthwest
Thu 1/16:00 amMDW - LGA
Nonstop2h 00mSouthwest
Deal found 12/20$223
This Expedia deal was found by Cheapflights users on 12/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3012:30 pmLGA - MDW
1 stop10h 42mFrontier
Thu 1/812:41 pmMDW - LGA
1 stop9h 33mFrontier
Deal found 12/20$232

Find flight deals from Pennsylvania to Midway

Keep the following information in mind while searching for Pennsylvania to Midway flight deals. Data was last updated December 22, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$111
(Frontier)

One-way from

$55
(Expedia)

Popular in

February

Cheapest in

September

Average price

$277

Good round-trip deal

$309 or less

Good one-way deal

$166 or less
Provider with most accurate pricing for Philadelphia-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Philadelphia-Chicago (CHI) flights.
Search Deals
From Pennsylvania to Chicago Midway
Search Deals
One-way flight from Pennsylvania to Chicago Midway
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Pennsylvania to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Pennsylvania to Chicago Midway.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Pennsylvania to Midway 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 December 22, 2025.
Use the filters below to find and compare flights from Pennsylvania to Chicago Midway Airport that are best for you.

Fly from

Pennsylvania

Fly to

Midway

Route

Depart

Return

Price

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 1/30

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Mon 2/2

6:05 am-9:10 am

Nonstop2h 05m

$139

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sun 1/25

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Fri 1/30

7:15 pm-10:20 pm

Nonstop2h 05m

$139

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Mon 1/19

9:40 pm-11:10 pm

Nonstop2h 30m

Chicago Midway

Wed 1/21

6:05 am-9:10 am

Nonstop2h 05m

$139

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 2/20

9:50 pm-11:20 pm

Nonstop2h 30m

Chicago Midway

Mon 2/23

6:05 pm-9:10 pm

Nonstop2h 05m

$139

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 1/14

9:45 pm-11:15 pm

Nonstop2h 30m

Chicago Midway

Wed 1/21

7:15 pm-10:20 pm

Nonstop2h 05m

$148

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 1/14

9:45 pm-11:15 pm

Nonstop2h 30m

Chicago Midway

Sun 1/18

6:05 am-9:10 am

Nonstop2h 05m

$148

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 1/17

8:20 am-1:40 pm

1 stop6h 20m

Chicago Midway

Sat 1/24

5:35 pm-8:40 pm

Nonstop2h 05m

$154

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 1/15

9:00 am-10:40 am

Nonstop2h 40m

Chicago Midway

Sun 1/18

5:55 pm-9:00 pm

Nonstop2h 05m

$157

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sun 1/18

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Sun 1/25

6:05 pm-9:10 pm

Nonstop2h 05m

$157

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 2/13

9:50 pm-11:20 pm

Nonstop2h 30m

Chicago Midway

Mon 2/16

6:00 am-9:05 am

Nonstop2h 05m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 60 results
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Best time to book a flight from Pennsylvania to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Pennsylvania 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 Pennsylvania to Chicago Midway Airport

What is the cheapest month to book a flight from Pennsylvania to Chicago Midway Airport?

Currently, December is the cheapest month in which you can book a flight from Pennsylvania to Chicago Midway Airport (average of $59). Flying from Pennsylvania to Chicago Midway Airport in June is currently the most expensive (average of $159). 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 PA to MDW?

Find hourly flight availability from Pennsylvania to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 22, 2025.

It’s optimal to fly from Pennsylvania to Chicago Midway Airport in the evening. By choosing this option you can save up to 31% on the cost of your flight, compared to a flight in the afternoon.

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

Use this chart to determine the cheapest time to fly round-trip from Pennsylvania to Midway. Price data was last updated on December 16, 2024.

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

How much does it cost to fly round-trip from Pennsylvania to Chicago Midway Airport?

Related info for your journey

Find useful and relevant information for your journey from Pennsylvania to Midway. 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 Pennsylvania to Chicago Midway Airport?

    For as low as $139, Southwest can have you in Chicago Midway Airport from Pennsylvania in 2h 40m. The distance between Pennsylvania and Chicago Midway Airport is about 722 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Pennsylvania to Chicago Midway Airport one-way?

    $38 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Frontier and Delta, with prices starting from $49 and $98, respectively.

  • What are the most popular routes from Pennsylvania to Chicago Midway Airport?

    The most popular flight routes from Pennsylvania to Chicago Midway Airport are Newark - Chicago Midway, New York John F Kennedy Intl - Chicago Midway and New York LaGuardia - Chicago Midway.

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

    Looking for the cheapest flight from Pennsylvania to Chicago Midway Airport? While on average our users pay $336, our data indicates the cheapest price to be $106. The most popular route (Newark - Chicago Midway), is priced around $119.

  • Can I find deals for flights from Pennsylvania to Midway that include hotel bookings?

    Yes. In addition to deals on Pennsylvania to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pennsylvania to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pennsylvania to Midway.

  • Can I find deals for business class flights from Pennsylvania to Midway?

    Yes. Cheapflights offers flight deals from Pennsylvania to Midway 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 Pennsylvania to Chicago Midway Airport?

    Currently, December is the cheapest month in which you can book a flight from Pennsylvania to Chicago Midway Airport (average of $59). Flying from Pennsylvania to Chicago Midway Airport in June is currently the most expensive (average of $159). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Pennsylvania to Midway

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Newark to O'Hare Intl flights
Boston to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Seattle to O'Hare Intl flights
Denver to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Los Angeles to Midway flights
Dulles Intl to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Newark to Midway flights
Ontario to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Tampa to O'Hare Intl flights
Orlando to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
LaGuardia to Midway flights
Fort Lauderdale to O'Hare Intl flights
Love Field to O'Hare Intl flights
Austin to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Atlanta to Midway flights
Hobby to O'Hare Intl flights
Orlando to Midway flights
San Diego to O'Hare Intl flights
Raleigh to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Miami to O'Hare Intl flights
Dulles Intl to Midway flights
San Francisco to Midway flights
Denver to Midway flights
Minneapolis to Midway flights
Detroit to O'Hare Intl flights
Las Vegas to O'Hare Intl flights
Boston to Midway flights
Philadelphia to Midway flights
Portland to O'Hare Intl flights
Love Field to Midway flights
Cleveland to O'Hare Intl flights
Hobby to Midway flights
George Bush Intcntl to Midway flights
Baltimore to Midway flights

Top 4 airlines flying from Pennsylvania to Midway

Discover the top 4 airlines that operate flights from Pennsylvania to Midway. 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 December 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$92Average$183FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$97Average$315FlexibilityNo cancel feeOn-time63%
DeltaCheapest$228Average$493FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$297Average$437FlexibilityNo cancel feeOn-time69%

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