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$73+ 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — MDW
Oct 19 — Oct 261
Sun 10/19
Sun 10/26
1 adult, Economy
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Cheapflights Tip: The best prices from Philadelphia to Chicago Midway are usually found in November or October, booked 69 days in advance, depart on a Friday or Saturday and return on a Friday

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 September 19, 2025.

Round-trip from

$111
(Kiwi.com)

One-way from

$73
(Kiwi.com)

Popular in

March

Cheapest in

November

Average price

$198

Good round-trip deal

$171 or less

Good one-way deal

$132 or less
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. 22% potential increase in price ($72 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 September 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 September 19, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:00 amPHL - MDW
Nonstop2h 11mFrontier
Thu 10/98:25 amMDW - PHL
Nonstop2h 02mFrontier
Deal found 9/17$111
This Priceline deal was found by Cheapflights users on 9/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/236:37 pmPHL - MDW
1 stop6h 09mFrontier
Fri 10/319:15 amMDW - PHL
Nonstop2h 04mFrontier
Deal found 9/17$113
This Flightnetwork deal was found by Cheapflights users on 9/16. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/311:19 pmPHL - MDW
Nonstop2h 14mFrontier
Fri 11/712:14 pmMDW - PHL
Nonstop2h 00mFrontier
Deal found 9/16$114
This CheapOair deal was found by Cheapflights users on 9/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:10 amPHL - MDW
Nonstop2h 15mFrontier
Mon 10/2012:13 pmMDW - PHL
Nonstop2h 00mFrontier
Deal found 9/16$116
This Priceline deal was found by Cheapflights users on 9/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:10 amPHL - MDW
Nonstop2h 15mFrontier
Fri 10/175:28 pmMDW - PHL
1 stop6h 39mFrontier
Deal found 9/16$117
This Booking.com deal was found by Cheapflights users on 9/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/195:05 pmPHL - MDW
1 stop17h 28mFrontier
Mon 11/39:15 amMDW - PHL
Nonstop2h 04mFrontier
Deal found 9/17$118
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/56:00 amPHL - MDW
Nonstop2h 11mFrontier
Thu 10/168:25 amMDW - PHL
Nonstop2h 02mFrontier
Deal found 9/16$119
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/266:10 amPHL - MDW
Nonstop2h 15mFrontier
Sun 11/28:32 amMDW - PHL
Nonstop2h 02mFrontier
Deal found 9/17$120
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/36:00 amPHL - MDW
Nonstop2h 11mFrontier
Mon 10/68:15 amMDW - PHL
Nonstop2h 01mFrontier
Deal found 9/17$121
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:00 amPHL - MDW
Nonstop2h 11mFrontier
Mon 10/68:15 amMDW - PHL
Nonstop2h 01mFrontier
Deal found 9/17$122
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:10 amPHL - MDW
Nonstop2h 15mFrontier
Fri 10/245:52 pmMDW - PHL
Nonstop2h 01mFrontier
Deal found 9/16$123

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 September 19, 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

Wed 10/29

5:25 am-6:30 am

Nonstop2h 05m

Chicago Midway

Tue 11/4

8:10 am-11:05 am

Nonstop1h 55m

$139

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 11/5

6:15 pm-7:25 pm

Nonstop2h 10m

Chicago Midway

Wed 11/12

2:25 pm-5:15 pm

Nonstop1h 50m

$139

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Tue 10/21

5:25 am-6:30 am

Nonstop2h 05m

Chicago Midway

Thu 10/23

9:15 pm-12:10 am

Nonstop1h 55m

$158

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Sun 11/16

5:45 am-6:55 am

Nonstop2h 10m

Chicago Midway

Tue 11/18

8:10 am-11:05 am

Nonstop1h 55m

$158

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Sat 10/25

5:10 pm-6:15 pm

Nonstop2h 05m

Chicago Midway

Sun 10/26

7:25 am-10:20 am

Nonstop1h 55m

$158

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Mon 10/20

8:35 pm-9:45 pm

Nonstop2h 10m

Chicago Midway

Wed 10/22

2:50 pm-5:45 pm

Nonstop1h 55m

$158

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 10/15

8:10 am-2:25 pm

1 stop7h 15m

Chicago Midway

Wed 10/22

2:50 pm-5:45 pm

Nonstop1h 55m

$184

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 2/18

2:10 pm-10:05 pm

2 stops8h 55m

Chicago Midway

Sat 2/21

6:15 pm-9:10 pm

Nonstop1h 55m

$184

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 10/15

8:10 am-2:25 pm

1 stop7h 15m

Chicago Midway

Sat 10/18

5:35 pm-8:30 pm

Nonstop1h 55m

$184

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 10/22

12:19 pm-4:09 pm

1 stop4h 50m

Chicago Midway

Tue 10/28

10:35 am-5:13 pm

1 stop5h 38m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/18

Showing 1-10 of 23 results
1
2
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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

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 September 12, 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 69 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, April is the cheapest month in which you can book a flight from Philadelphia to Chicago Midway Airport (average of $160). Flying from Philadelphia 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 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 September 19, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 32% 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 September 14, 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. Monday at noon 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 Philadelphia to Chicago Midway Airport?

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 September 19, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, 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
4,242 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

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
United Airlines
7.4
Good
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

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
3,171 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

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. 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 4 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 05m. 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 $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. Search Cheapflights for deals from Southwest and United Airlines - these airlines can fly you to your destination from $167 and $194, respectively. You may be able to fly from Philadelphia to Chicago Midway Airport for 75% 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 $237 for a flight from Philadelphia to Chicago Midway Airport. The cheapest flight overall is $74 while the most popular route, (Philadelphia - Chicago Midway) is currently priced at $103.

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

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

Browse thousands of different options on Cheapflights for your next trip

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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 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 September 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$61Average$167FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$167Average$301FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$194Average$411FlexibilityNo cancel feeOn-time69%

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