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$64+ 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — MDW
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Find 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 November 3, 2025.

This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/244:50 pmPHL - MDW
Nonstop2h 16mFrontier
Fri 11/288:41 pmMDW - PHL
Nonstop1h 57mFrontier
Deal found 11/1$109
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:25 amJFK - MDW
1 stop8h 34mFrontier
Wed 12/102:49 pmMDW - JFK
1 stop9h 10mFrontier
Deal found 11/2$110
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.
Thu 12/1110:00 pmPHL - MDW
1 stop25h 39mFrontier
Mon 12/1512:18 pmMDW - PHL
1 stop16h 13mFrontier
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.
Sat 11/151:20 pmLGA - MDW
1 stop6h 19mFrontier
Mon 11/171:37 pmMDW - LGA
1 stop8h 50mFrontier
Deal found 11/2$110
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.
Sat 12/66:25 amJFK - MDW
1 stop8h 34mFrontier
Mon 12/88:42 pmMDW - JFK
1 stop11h 19mFrontier
Deal found 11/2$111
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/186:20 amJFK - MDW
1 stop6h 18mFrontier
Thu 11/205:30 pmMDW - JFK
1 stop15h 32mFrontier
Deal found 11/2$117
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/196:24 amLGA - MDW
1 stop7h 17mFrontier
Wed 12/32:49 pmMDW - LGA
1 stop7h 16mFrontier
Deal found 10/31$118
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 11/166:15 amPHL - MDW
Nonstop2h 15mFrontier
Thu 11/209:30 amMDW - PHL
1 stop27h 41mFrontier
Deal found 11/2$119
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:20 amLGA - MDW
1 stop8h 39mFrontier
Mon 12/86:15 amMDW - LGA
1 stop9h 14mFrontier
Deal found 11/3$120
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1712:30 pmLGA - MDW
1 stop7h 09mFrontier
Wed 11/191:56 pmMDW - LGA
1 stop8h 31mFrontier
Deal found 11/1$121
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/41:00 pmJFK - MDW
1 stop6h 08mFrontier
Mon 12/88:42 pmMDW - JFK
1 stop11h 19mFrontier
Deal found 11/3$122
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1310:55 pmLGA - MDW
1 stop13h 13mFrontier
Mon 12/1512:18 pmMDW - LGA
1 stop8h 42mFrontier
Deal found 11/3$122

Cheap flight deals from Pennsylvania to Midway

Keep the following information in mind while searching for Pennsylvania to Midway flight deals. Data was last updated November 3, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$109
(Kiwi.com)

One-way from

$64
(Southwest)

Popular in

March

Cheapest in

September

Average price

$198

Good round-trip deal

$149 or less

Good one-way deal

$142 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. 16% potential increase in price ($50 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 November 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 November 3, 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

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 12/3

6:00 am-9:40 am

1 stop4h 40m

Chicago Midway

Wed 12/10

6:05 pm-8:30 pm

Nonstop1h 25m

$127

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 12/6

8:35 am-10:00 am

Nonstop2h 25m

Chicago Midway

Mon 12/8

7:15 pm-10:20 pm

Nonstop2h 05m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 12/3

6:00 am-7:30 am

Nonstop2h 30m

Chicago Midway

Wed 12/10

7:15 pm-10:20 pm

Nonstop2h 05m

$137

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 12/5

5:19 pm-10:12 pm

1 stop5h 53m

Chicago Midway

Sun 12/7

6:15 am-4:24 pm

1 stop9h 09m

$142

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 11/13

9:00 am-10:25 am

Nonstop2h 25m

Chicago Midway

Mon 11/17

7:15 pm-10:20 pm

Nonstop2h 05m

$143

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 1/29

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Sun 2/1

6:05 am-9:10 am

Nonstop2h 05m

$148

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Mon 11/24

6:00 am-1:07 pm

1 stop8h 07m

Chicago Midway

Thu 11/27

5:34 pm-12:21 am

1 stop5h 47m

$157

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 12/2

4:45 pm-6:15 pm

Nonstop2h 30m

Chicago Midway

Tue 12/9

7:15 pm-10:20 pm

Nonstop2h 05m

$157

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Sun 1/11

5:50 am-7:05 am

Nonstop2h 15m

Chicago Midway

Tue 1/13

5:30 pm-8:20 pm

Nonstop1h 50m

$158

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 12/4

9:10 am-10:40 am

Nonstop2h 30m

Chicago Midway

Sat 12/6

2:40 pm-9:15 pm

1 stop5h 35m

$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 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, November is the cheapest month in which you can book a flight from Pennsylvania to Chicago Midway Airport (average of $44). 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 November 3, 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. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 $127, Southwest can have you in Chicago Midway Airport from Pennsylvania in 4h 40m. The distance between Pennsylvania and Chicago Midway Airport 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 Pennsylvania to Chicago Midway Airport one-way?

    $65 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $69 and $89, 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 New York John F Kennedy Intl - Chicago Midway, New York LaGuardia - Chicago Midway and Washington, D.C. Dulles Intl - 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 $230, our data indicates the cheapest price to be $69. The most popular route (New York John F Kennedy Intl - Chicago Midway), is priced around $110.

  • 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, November is the cheapest month in which you can book a flight from Pennsylvania to Chicago Midway Airport (average of $44). 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
Merrillville
Lansing
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
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Seattle to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Denver to O'Hare Intl flights
Boston to O'Hare Intl flights
Atlanta to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Atlanta to Midway flights
Dulles Intl to Midway flights
Baltimore to Midway flights
Ontario to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Hobby to Midway flights
Tampa to O'Hare Intl flights
San Francisco to Midway flights
Charlotte to O'Hare Intl flights
Austin to O'Hare Intl flights
Reagan-National to Midway flights
Cleveland to O'Hare Intl flights
Denver to Midway flights
Minneapolis to Midway flights
San Diego to O'Hare Intl flights
Portland to O'Hare Intl flights
LaGuardia to Midway flights
Fort Lauderdale to O'Hare Intl flights
Miami to O'Hare Intl flights
Hartford to O'Hare Intl flights
Orlando to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Love Field to O'Hare Intl flights
Philadelphia to Midway flights
Los Angeles to Midway flights
Orlando to Midway flights
Boston to Midway flights
San Jose to O'Hare Intl flights
Hobby to O'Hare Intl flights
Salt Lake City to O'Hare Intl flights
Sacramento to O'Hare Intl flights

Top 3 airlines flying from Pennsylvania to Midway

Discover the top 3 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$61Average$179FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$97Average$320FlexibilityNo cancel feeOn-time63%
DeltaCheapest$228Average$550FlexibilityNo cancel feeOn-timeN/A

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