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$49+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — MDW
Apr 1 — Apr 81
Tue 4/1
Tue 4/8
1 adult, Economy
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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 March 27, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$137
(Southwest)

One-way from

$49
(Southwest)

Popular in

February

Cheapest in

September

Average price

$293

Good round-trip deal

$278 or less

Good one-way deal

$161 or less
Provider with most accurate pricing for Philadelphia-Chicago (CHI) flight deals.
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From Pennsylvania to Chicago Midway
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One-way flight from Pennsylvania to Chicago Midway
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Highest demand for flights based on searches. 29% potential increase in price ($86 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from Pennsylvania to Chicago Midway.
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Price to beat on a one-way flight from Pennsylvania to Chicago Midway.
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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 March 27, 2025.

This Southwest deal was found by Cheapflights users on 3/27. 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.
Fri 4/182:15 pmPIT - MDW
Nonstop1h 30mSouthwest
Sat 4/195:45 amMDW - PIT
1 stop4h 50mSouthwest
Deal found 3/27$137
This Southwest deal was found by Cheapflights users on 3/26. 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.
Sat 5/247:15 amLGA - MDW
Nonstop2h 25mSouthwest
Sat 5/246:15 pmMDW - LGA
Nonstop2h 10mSouthwest
Deal found 3/26$137
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/38:23 pmPHL - MDW
Nonstop2h 17mFrontier
Tue 4/82:36 pmMDW - PHL
Nonstop2h 00mFrontier
Deal found 3/27$167
This Southwest deal was found by Cheapflights users on 3/26. 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.
Sat 4/266:25 amPHL - MDW
Nonstop2h 10mSouthwest
Wed 4/308:25 amMDW - PHL
Nonstop2h 00mSouthwest
Deal found 3/26$168
This Delta deal was found by Cheapflights users on 3/25. 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.
Wed 4/236:25 pmPIT - MDW
1 stop4h 57mDelta
Thu 4/245:59 pmMDW - PIT
1 stop4h 04mDelta
Deal found 3/25$177
This Delta deal was found by Cheapflights users on 3/27. 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.
Thu 4/245:55 amEWR - MDW
1 stop13h 25mDelta
Mon 4/283:02 pmMDW - EWR
1 stop16h 36mDelta
Deal found 3/27$177
This Southwest deal was found by Cheapflights users on 3/26. 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 5/266:55 amDCA - MDW
Nonstop2h 00mSouthwest
Tue 5/278:50 pmMDW - DCA
Nonstop1h 50mSouthwest
Deal found 3/26$177
This CheapOair deal was found by Cheapflights users on 3/27. 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 4/139:23 pmPIT - MDW
1 stop16h 05mFrontier
Tue 4/154:40 pmMDW - PIT
1 stop17h 08mFrontier
Deal found 3/27$180
This Frontier deal was found by Cheapflights users on 3/27. 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.
Mon 4/216:00 pmDCA - MDW
1 stop7h 21mFrontier
Tue 4/226:45 amMDW - DCA
1 stop14h 14mFrontier
Deal found 3/27$188
This Cheapflightsfares deal was found by Cheapflights users on 3/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/24:35 pmIAD - MDW
1 stop5h 58mFrontier
Thu 4/310:19 amMDW - IAD
1 stop5h 45mFrontier
Deal found 3/26$196
This Delta deal was found by Cheapflights users on 3/27. 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.
Thu 5/86:00 amIAD - MDW
1 stop3h 40mDelta
Tue 5/134:15 pmMDW - IAD
1 stop6h 20mDelta
Deal found 3/27$197
This Frontier deal was found by Cheapflights users on 3/27. 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.
Fri 5/26:00 amJFK - MDW
1 stop8h 34mFrontier
Sun 5/46:45 pmMDW - JFK
1 stop11h 44mFrontier
Deal found 3/27$198

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 March 27, 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

Fri 4/18

2:15 pm-2:45 pm

Nonstop1h 30m

Chicago Midway

Sat 4/19

5:45 am-11:35 am

1 stop4h 50m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 5/24

7:15 am-8:40 am

Nonstop2h 25m

Chicago Midway

Sat 5/24

6:15 pm-9:25 pm

Nonstop2h 10m

$137

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Sat 4/26

6:25 am-7:35 am

Nonstop2h 10m

Chicago Midway

Wed 4/30

8:25 am-11:25 am

Nonstop2h 00m

$168

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Tue 4/15

6:31 pm-7:51 pm

Nonstop2h 20m

Chicago Midway

Thu 4/17

4:30 pm-7:28 pm

Nonstop1h 58m

$169

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 4/23

6:25 pm-10:22 pm

1 stop4h 57m

Chicago Midway

Thu 4/24

5:59 pm-11:03 pm

1 stop4h 04m

$177

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 4/24

5:55 am-6:20 pm

1 stop13h 25m

Chicago Midway

Mon 4/28

3:02 pm-8:38 am

1 stop16h 36m

$177

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 5/26

6:55 am-7:55 am

Nonstop2h 00m

Chicago Midway

Tue 5/27

8:50 pm-11:40 pm

Nonstop1h 50m

$177

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sun 4/13

9:23 pm-12:28 pm

1 stop16h 05m

Chicago Midway

Tue 4/15

4:40 pm-10:48 am

1 stop17h 08m

$180

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 4/21

6:00 pm-12:21 am

1 stop7h 21m

Chicago Midway

Tue 4/22

6:45 am-9:59 pm

1 stop14h 14m

$188

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 5/8

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Mon 5/12

9:20 am-4:44 pm

1 stop6h 24m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 58 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, April is the cheapest month in which you can book a flight from Pennsylvania to Chicago Midway Airport (average of $160). Flying from Pennsylvania to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 March 27, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Pennsylvania to Chicago Midway Airport as you normally would.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated March 27, 2025.
See what other customers who have flown with Southwest, Delta and Allegiant Air from Pennsylvania to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,273 reviews

Boarding

8.2

Crew

8.6

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,273 reviews
Southwest
8.1
Very good
4,273 reviews

Boarding

8.2

Crew

8.6

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,895 reviews
Southwest
8.1
Very good
4,273 reviews

Boarding

8.2

Crew

8.6

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
731 reviews
Southwest
8.1
Very good
4,273 reviews

Boarding

8.2

Crew

8.6

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,272 reviews
Southwest
8.1
Very good
4,273 reviews

Boarding

8.2

Crew

8.6

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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.

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

    $49 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Delta and Frontier, with prices starting from $79 and $86, 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 $303, our data indicates the cheapest price to be $81. The most popular route (Newark - Chicago Midway), is priced around $179.

  • 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, April is the cheapest month in which you can book a flight from Pennsylvania to Chicago Midway Airport (average of $160). Flying from Pennsylvania to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 Pennsylvania?

Book flights to Pennsylvania if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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.
Newark to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Newark to Midway flights
John F Kennedy Intl to Midway flights
Boston to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Baltimore to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Seattle to O'Hare Intl flights
Ontario to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
San Francisco to Midway flights
Denver to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
San Diego to O'Hare Intl flights
LaGuardia to Midway flights
Dulles Intl to Midway flights
Los Angeles to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Hobby to O'Hare Intl flights
Atlanta to Midway flights
Austin to O'Hare Intl flights
Orlando to O'Hare Intl flights
Baltimore to Midway flights
Boston to Midway flights
Burbank to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Hartford to O'Hare Intl flights
Miami to O'Hare Intl flights
Minneapolis to Midway flights
Reagan-National to Midway flights
Charlotte to O'Hare Intl flights
Philadelphia to Midway flights
George Bush Intcntl to O'Hare Intl flights
Seattle to Midway flights
Tampa to O'Hare Intl flights
Love Field to O'Hare Intl flights
Portland to O'Hare Intl flights
San Jose to O'Hare Intl flights
Hobby to Midway flights
Oakland to O'Hare Intl flights
Cleveland to O'Hare Intl flights

Top 5 airlines flying from Pennsylvania to Midway

Discover the top 5 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 March 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$55Average$137FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$132Average$301FlexibilityNo cancel feeOn-time63%
DeltaCheapest$181Average$409FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$188Average$266FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$193Average$353FlexibilityNo cancel feeOn-time69%
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