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$88+ 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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — MDW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Philadelphia to Chicago Midway are usually found in September or August, booked 77 days in advance, depart on a Friday or Saturday and return on a Saturday

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 June 12, 2025.

Round-trip from

$168
(Southwest)

One-way from

$88
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$264

Good round-trip deal

$213 or less

Good one-way deal

$142 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. 30% potential increase in price ($97 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/10. 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.
Wed 8/66:30 amPHL - MDW
Nonstop2h 00mSouthwest
Sun 8/108:50 amMDW - PHL
Nonstop2h 00mSouthwest
Deal found 6/10$168
This FlightHub deal was found by Cheapflights users on 6/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/410:38 pmPHL - MDW
Nonstop2h 13mFrontier
Fri 7/116:40 pmMDW - PHL
Nonstop2h 05mFrontier
Deal found 6/11$169
This Delta deal was found by Cheapflights users on 6/12. 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.
Fri 8/84:05 pmPHL - MDW
1 stop6h 37mDelta
Mon 8/111:08 pmMDW - PHL
1 stop5h 10mDelta
Deal found 6/12$198

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 June 12, 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 8/6

6:30 am-7:30 am

Nonstop2h 00m

Chicago Midway

Sun 8/10

8:50 am-11:50 am

Nonstop2h 00m

$168

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 7/4

10:38 pm-11:51 pm

Nonstop2h 13m

Chicago Midway

Fri 7/11

6:40 pm-9:45 pm

Nonstop2h 05m

$169

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 8/8

4:05 pm-9:42 pm

1 stop6h 37m

Chicago Midway

Mon 8/11

1:08 pm-7:18 pm

1 stop5h 10m

$198

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 8/1

10:38 pm-11:51 pm

Nonstop2h 13m

$88

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 8/21

5:35 pm-10:50 pm

1 stop6h 15m

$89

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 7/23

5:30 am-9:45 am

1 stop5h 15m

$105

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Sun 7/20

6:00 am-9:41 am

2 stops28h 41m

$170

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 June 9, 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 62 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 June 12, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 35% 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 June 8, 2025.

Travelers seeking maximum savings on their Philadelphia to Chicago Midway Airport flight should consider departing on Tuesday 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.

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 June 12, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Frontier from Philadelphia to Chicago by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 3 outbound flights to Chicago Midway per day.

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

    Currently priced at $168, Southwest will fly you from Philadelphia to Chicago Midway Airport and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Frontier and Delta - these airlines can fly you to your destination from $169 and $203, respectively. You may be able to fly from Philadelphia to Chicago Midway Airport for 26% less than the average price by searching for these airlines.

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

    One-way options have recently been found by users for as low as $88 on Frontier. Other airlines that offer cheap prices include Southwest from $89 and Delta from $105 one-way.

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

    On average you can expect to pay $263 for a flight from Philadelphia to Chicago Midway Airport. The cheapest flight overall is $94 while the most popular route, (Philadelphia - Chicago Midway) is currently priced at $126.

  • 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 Philadelphia?

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

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$55Average$140FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$170Average$306FlexibilityNo cancel feeOn-time63%
DeltaCheapest$188Average$310FlexibilityNo cancel feeOn-timeN/A

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