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$89+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — MDW
Apr 19 — Apr 261
Sun 4/19
Sun 4/26
1 adult, Economy
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Find cheap flights from Philadelphia to Midway with Cheapflights

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

Cheap 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 March 20, 2026.

This Frontier deal was found by Cheapflights users on 3/15. 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 4/2911:02 am
PHL
-
MDW
1 stop9h 29m
Frontier
Wed 5/612:04 pm
MDW
-
PHL
1 stop6h 06m
Frontier
Deal found 3/15$179
This Expedia deal was found by Cheapflights users on 3/17. 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 4/1411:02 am
PHL
-
MDW
1 stop12h 12m
Frontier
Tue 4/216:10 am
MDW
-
PHL
1 stop6h 08m
Frontier
Deal found 3/17$180
This Frontier deal was found by Cheapflights users on 3/19. 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 4/1411:02 am
PHL
-
MDW
1 stop9h 29m
Frontier
Thu 4/166:00 am
MDW
-
PHL
1 stop10h 49m
Frontier
Deal found 3/19$181
This Frontier deal was found by Cheapflights users on 3/15. 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 5/316:30 am
PHL
-
MDW
1 stop5h 42m
Frontier
Tue 8/48:05 am
MDW
-
PHL
1 stop10h 22m
Frontier
Deal found 3/15$185
This Priceline deal was found by Cheapflights users on 3/18. 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.
Tue 8/116:30 am
PHL
-
MDW
1 stop5h 42m
Frontier
Tue 8/1112:27 pm
MDW
-
PHL
1 stop5h 36m
Frontier
Deal found 3/18$190
This CheapOair deal was found by Cheapflights users on 3/17. 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 4/177:37 pm
PHL
-
MDW
1 stop21h 23m
Frontier
Wed 4/222:15 pm
MDW
-
PHL
1 stop9h 39m
Frontier
Deal found 3/17$191
This CheapOair deal was found by Cheapflights users on 3/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1710:38 pm
PHL
-
MDW
1 stop18h 22m
Frontier
Fri 4/246:49 pm
MDW
-
PHL
1 stop11h 52m
Frontier
Deal found 3/20$192
This Booking.com deal was found by Cheapflights users on 3/16. 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.
Wed 4/2211:02 am
PHL
-
MDW
1 stop9h 29m
Frontier
Mon 4/279:14 am
MDW
-
PHL
1 stop24h 24m
Frontier
Deal found 3/16$193
This Trip.com deal was found by Cheapflights users on 3/18. 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.
Mon 4/1312:10 pm
PHL
-
MDW
1 stop11h 09m
Frontier
Thu 4/166:00 am
MDW
-
PHL
1 stop10h 49m
Frontier
Deal found 3/18$199
This Frontier deal was found by Cheapflights users on 3/17. 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 4/2211:02 am
PHL
-
MDW
1 stop12h 12m
Frontier
Wed 4/292:15 pm
MDW
-
PHL
1 stop9h 39m
Frontier
Deal found 3/17$201
This Frontier deal was found by Cheapflights users on 3/19. 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 5/294:35 pm
PHL
-
MDW
1 stop6h 27m
Frontier
Mon 6/112:04 pm
MDW
-
PHL
1 stop9h 06m
Frontier
Deal found 3/19$202

Find 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 March 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$180
(Frontier)

One-way from

$89
(Super.com)

Popular in

March

Cheapest in

November

Average price

$461

Good round-trip deal

$348 or less

Good one-way deal

$197 or less
Provider with most accurate pricing for Philadelphia-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Philadelphia-Chicago Midway flights.
Search Deals
From Philadelphia to Chicago Midway
Search Deals
One-way flight from Philadelphia to Chicago Midway
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($63 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Philadelphia to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Philadelphia to Chicago Midway.
Search Deals

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 March 20, 2026.
Use the filters below to find and compare flights from Philadelphia to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Sat 4/18

3:45 pm-5:00 pm

Nonstop2h 15m

Chicago Midway

Mon 4/20

3:25 pm-6:25 pm

Nonstop2h 00m

$237

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Sat 5/16

6:45 pm-10:35 pm

1 stop4h 50m

Chicago Midway

Mon 5/18

5:40 pm-11:05 pm

1 stop4h 25m

$237

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 5/8

6:00 pm-7:10 pm

Nonstop2h 10m

Chicago Midway

Sun 5/10

10:50 am-6:25 pm

1 stop6h 35m

$247

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Mon 5/4

7:10 pm-10:45 pm

1 stop4h 35m

Chicago Midway

Thu 5/7

11:40 am-4:45 pm

1 stop4h 05m

$257

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 4/1

4:55 pm-12:05 am

1 stop8h 10m

Chicago Midway

Sun 4/19

7:40 am-10:35 am

Nonstop1h 55m

$274

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Sun 4/19

2:05 pm-3:15 pm

Nonstop2h 10m

Chicago Midway

Fri 4/24

3:25 pm-6:25 pm

Nonstop2h 00m

$286

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Sun 8/30

8:50 pm-10:00 pm

Nonstop2h 10m

Chicago Midway

Wed 9/2

1:00 pm-4:00 pm

Nonstop2h 00m

$291

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 4/16

6:35 pm-11:55 pm

1 stop6h 20m

Chicago Midway

Sun 4/19

4:05 pm-11:15 pm

1 stop6h 10m

$296

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 7/29

4:35 pm-6:00 pm

Nonstop2h 25m

Chicago Midway

Mon 8/3

2:45 pm-12:20 am

2 stops8h 35m

$306
Quickest round-trip

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 6/5

12:50 pm-1:50 pm

Nonstop2h 00m

Chicago Midway

Wed 6/10

1:10 pm-4:10 pm

Nonstop2h 00m

$323

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/15

Showing 1-10 of 21 resultsSorted by cheapest first
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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy2 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Philadelphia-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 March 13, 2026.

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, December is the cheapest month in which you can book a flight from Philadelphia to Chicago Midway Airport (average of $48). Flying from Philadelphia to Chicago Midway Airport in August is currently the most expensive (average of $130). 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 March 20, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 31% 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 March 14, 2026.

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

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Philadelphia to Chicago Midway Airport trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

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 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 March 20, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andFrontier 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
4,324 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,324 reviews
Southwest
8.0
Very good
4,324 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,454 reviews
Southwest
8.0
Very good
4,324 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
3,024 reviews
Southwest
8.0
Very good
4,324 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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. 3 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 Southwest to get the fastest option. Airlines will cover a distance of 666 mi. All flights are typically nonstop.

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

    Currently priced at $90, 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. Search Cheapflights for deals from Southwest and United Airlines - these airlines can fly you to your destination from $158 and $297, respectively. You may be able to fly from Philadelphia to Chicago Midway Airport for 67% 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 $334 for a flight from Philadelphia to Chicago Midway Airport. The cheapest flight overall is $128 while the most popular route, (Philadelphia - Chicago Midway) is currently priced at $191.

  • 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, December is the cheapest month in which you can book a flight from Philadelphia to Chicago Midway Airport (average of $48). Flying from Philadelphia to Chicago Midway Airport in August is currently the most expensive (average of $130). 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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Top 3 airlines flying from Philadelphia to Midway

Discover the top 3 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 March 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$181FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$158Average$309FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$297Average$461FlexibilityNo cancel feeOn-time69%

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