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$68+ Cheap flights from Philadelphia (PHL) 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — MDW
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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Find cheap flights from Philadelphia to Midway with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Philadelphia to Chicago Midway are usually found in November or December, booked 12 days in advance, depart on a Friday or Thursday and return on a Monday

Cheap flight deals from Philadelphia to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Philadelphia (PHL) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 4, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$110
(CheapOair)

One-way from

$69
(Priceline)

Popular in

March

Cheapest in

November

Average price

$167

Good round-trip deal

$149 or less

Good one-way deal

$142 or less
Provider with most accurate pricing for Philadelphia-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Philadelphia-Chicago Midway flights.
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From Philadelphia to Chicago Midway
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One-way flight from Philadelphia to Chicago Midway
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Highest demand for flights based on searches. 21% potential increase in price ($68 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 November 2025
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Price to beat on a round-trip flight from Philadelphia to Chicago Midway.
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Price to beat on a one-way flight from Philadelphia to Chicago Midway.
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Find flight deals from Philadelphia to Midway

Cheapest flights from Philadelphia to Midway
Explore the most affordable flight options available from Philadelphia to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2025.

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.
Mon 11/177:00 amPHL - MDW
1 stop11h 01mFrontier
Thu 11/209:30 amMDW - PHL
1 stop27h 41mFrontier
Deal found 11/3$110
This CheapOair deal was found by Cheapflights users on 11/4. 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.
Wed 11/267:16 amPHL - MDW
1 stop10h 41mFrontier
Mon 12/17:10 pmMDW - PHL
Nonstop1h 56mFrontier
Deal found 11/4$118
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.
Mon 11/244:50 pmPHL - MDW
Nonstop2h 16mFrontier
Mon 12/17:10 pmMDW - PHL
Nonstop1h 56mFrontier
Deal found 11/2$119
This CheapOair deal was found by Cheapflights users on 11/4. 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.
Fri 11/215:40 pmPHL - MDW
1 stop24h 27mFrontier
Sun 11/238:04 pmMDW - PHL
Nonstop1h 57mFrontier
Deal found 11/4$121
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/267:16 amPHL - MDW
1 stop10h 41mFrontier
Sat 11/298:29 pmMDW - PHL
Nonstop1h 57mFrontier
Deal found 11/3$122
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.
Fri 12/121:46 pmPHL - MDW
1 stop9h 26mFrontier
Mon 12/1512:18 pmMDW - PHL
1 stop16h 13mFrontier
Deal found 11/2$124
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.
Sun 11/167:00 amPHL - MDW
1 stop11h 11mFrontier
Thu 11/209:30 amMDW - PHL
1 stop10h 52mFrontier
Deal found 11/2$128
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.
Fri 12/57:42 pmPHL - MDW
1 stop27h 48mFrontier
Sun 12/72:01 pmMDW - PHL
1 stop23h 38mFrontier
Deal found 11/3$138
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1611:40 amPHL - MDW
Nonstop2h 10mSouthwest
Tue 12/166:05 pmMDW - PHL
Nonstop1h 55mSouthwest
Deal found 11/2$139
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.
Fri 12/121:46 pmPHL - MDW
1 stop9h 26mFrontier
Sun 12/1412:18 pmMDW - PHL
1 stop16h 13mFrontier
Deal found 11/2$142

Cheapflights Fare Finder

 
Customize your flight search to find flights from Philadelphia 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 4, 2025.
Use the filters below to find and compare flights from Philadelphia to Chicago Midway Airport that are best for you.

Fly from

Philadelphia

Fly to

Midway

Route

Depart

Return

Price

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 1/8

1:00 pm-11:25 pm

1 stop11h 25m

Chicago Midway

Mon 1/12

3:52 pm-12:50 am

1 stop7h 58m

$110

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 2/18

5:45 pm-7:00 pm

Nonstop2h 15m

Chicago Midway

Wed 2/25

5:30 pm-8:20 pm

Nonstop1h 50m

$139

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Mon 1/26

5:45 pm-7:00 pm

Nonstop2h 15m

Chicago Midway

Wed 1/28

5:30 pm-8:20 pm

Nonstop1h 50m

$148

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 12/3

4:00 pm-5:10 pm

Nonstop2h 10m

Chicago Midway

Wed 12/10

11:05 am-2:00 pm

Nonstop1h 55m

$149

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 2/18

2:10 pm-7:05 pm

1 stop5h 55m

Chicago Midway

Mon 2/23

9:40 am-12:35 pm

Nonstop1h 55m

$158

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 2/18

1:50 pm-6:05 pm

1 stop5h 15m

Chicago Midway

Sat 2/21

12:45 pm-6:00 pm

1 stop4h 15m

$159

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 1/16

5:05 pm-9:40 pm

1 stop5h 35m

Chicago Midway

Sun 1/18

6:10 am-11:30 am

1 stop4h 20m

$168

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 12/24

11:40 am-5:19 pm

1 stop6h 39m

Chicago Midway

Thu 1/1

6:08 pm-11:17 pm

1 stop4h 09m

$177

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 12/12

5:45 am-6:55 am

Nonstop2h 10m

Chicago Midway

Mon 12/15

2:30 pm-5:20 pm

Nonstop1h 50m

$177

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 12/4

6:00 am-7:15 am

Nonstop2h 15m

Chicago Midway

Thu 12/11

8:10 am-11:05 am

Nonstop1h 55m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 21 results
1
2
3

Compare providers for flights from Philadelphia to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Philadelphia to Midway in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Philadelphia-Chicago Midway Airport flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Philadelphia-Chicago Midway Airport flight deals on Cheapflights vs. CheapOair >95% of the time. Price accuracy is based on data collected from Philadelphia-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Philadelphia-Chicago Midway Airport flights, Cheapflights users trust CheapOair the most. CheapOair has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Philadelphia-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Philadelphia to Midway

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

How far ahead should I book a flight from Philadelphia to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from Philadelphia to Midway. Price data was last updated on October 31, 2025.

The price you pay for your flight from Philadelphia to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 12 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, November is the cheapest month in which you can book a flight from Philadelphia to Chicago Midway Airport (average of $44). Flying from Philadelphia to Chicago Midway Airport in February 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 PHL to MDW?

Find hourly flight availability from Philadelphia 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 4, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 25% on flights from Philadelphia to Chicago Midway Airport by exploring options for tickets in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Philadelphia to Midway. Price data was last updated on November 2, 2025.

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

The best insider tips for Philadelphia to Chicago Midway Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Philadelphia to Chicago Midway Airport trip
Airports
PHL

For a quick check-in, verify your airline’s terminal before arriving at PHL. Terminals are spread out, and only some are linked by indoor hallways.

Read more about PHLby Mark Chesnut
MDW

Use the Orange Line train for a quick, affordable ride from MDW to downtown Chicago in under 30 minutes.

Read more about MDWby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Mark Chesnut

Mark Chesnut

Expert on PHL

Mark Chesnut

Mark Chesnut

Mark Chesnut is a travel writer and public speaker with more than 30 years of experience. The 2019 winner of the NLGJA Excellence in Travel Writing Award, Mark is the author of the book “Prepare for Departure” and has covered air travel for multiple top consumer and trade media outlets.

Read more

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 November 4, 2025.
Read reviews from past customers who have flown Southwest and Frontier from Philadelphia to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

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
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

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
3,116 reviews
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

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 Philadelphia to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Philadelphia to Chicago Midway?

    Philadelphia (PHL), located 7.0 mi from the city center, is the airport you fly out of when you book flights from Philadelphia to Chicago Midway. 2 airlines have flights from Philadelphia to Chicago Midway on a regular basis. Booking flights from Philadelphia to Chicago Midway should not be difficult; the airport handles an average of 2 outbound flights to Chicago Midway per day.

  • How long is the flight from Philadelphia to Chicago Midway Airport?

    There are many flights that can get you from Philadelphia to Chicago Midway Airport in 2h 15m. Fly via Frontier or Southwest to get the fastest option. Airlines will cover a distance of 666 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Philadelphia to Chicago Midway Airport round-trip?

    Currently priced at $61, Frontier will fly you from Philadelphia to Chicago Midway Airport and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Southwest for as low as $167. You may be able to fly from Philadelphia to Chicago Midway Airport for 76% less than the average price by searching for these airlines.

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

    On average you can expect to pay $230 for a flight from Philadelphia to Chicago Midway Airport. The cheapest flight overall is $69 while the most popular route, (Philadelphia - Chicago Midway) is currently priced at $119.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Philadelphia to Chicago Midway Airport (average of $44). Flying from Philadelphia to Chicago Midway Airport in February 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 Philadelphia to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Philadelphia to Midway

Discover the top 2 airlines that operate flights from Philadelphia 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 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$61Average$179FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$167Average$322FlexibilityNo cancel feeOn-time63%

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