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$99+ 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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Philadelphia to Chicago Midway are usually found in May or August, booked 78 days in advance, depart on a Saturday or Thursday 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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$200
(Cheapflightsfares)

One-way from

$99
(Delta)

Popular in

February

Cheapest in

May

Average price

$335

Good round-trip deal

$328 or less

Good one-way deal

$192 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.
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From Philadelphia to Chicago Midway
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One-way flight from Philadelphia to Chicago Midway
Search Deals
Highest demand for flights based on searches. 29% potential increase in price ($72 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/810:29 amPHL - MDW
1 stop6h 43mDelta
Tue 4/1512:48 pmMDW - PHL
1 stop4h 32mDelta
Deal found 2/19$197
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/21:21 pmPHL - MDW
1 stop7h 14mFrontier
Sun 4/138:00 amMDW - PHL
Nonstop2h 02mFrontier
Deal found 2/20$200
This Southwest deal was found by Cheapflights users on 2/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/26:25 amPHL - MDW
Nonstop2h 15mSouthwest
Thu 4/38:15 amMDW - PHL
Nonstop1h 55mSouthwest
Deal found 2/19$207

Find flights from Philadelphia to Midway within your budget

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 February 20, 2025.

Fly from

Philadelphia

Fly to

Midway

Route

Depart

Return

Price

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 4/2

1:21 pm-7:35 pm

1 stop7h 14m

Chicago Midway

Sun 4/13

8:00 am-11:02 am

Nonstop2h 02m

$200

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Tue 4/8

8:05 am-1:40 pm

1 stop6h 35m

Chicago Midway

Tue 4/8

6:25 pm-9:20 pm

Nonstop1h 55m

$207

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 4/2

12:28 pm-6:02 pm

1 stop6h 34m

Chicago Midway

Fri 4/4

4:59 pm-12:46 am

1 stop6h 47m

$262

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 3/5

10:03 am-5:36 pm

3 stops32h 33m

Chicago Midway

Fri 3/7

8:40 am-8:58 am

3 stops23h 18m

$390

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 4/2

6:00 am-8:45 am

1 stop3h 45m

$99

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 3/14

8:26 am-11:58 pm

1 stop16h 32m

$110

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 5/1

5:50 am-6:55 am

Nonstop2h 05m

$119

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Mon 3/24

6:55 am-5:46 pm

2 stops35h 51m

$170

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy1 starTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*2 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 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.

Travel insights for flights from Philadelphia to Midway

Get recent, data-driven insights about flights from Philadelphia to Midway including ideal travel times, pricing trends, and more.

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 February 14, 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 February 20, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 50% 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 February 16, 2025.

Travelers seeking maximum savings on their Philadelphia to Chicago Midway Airport flight should consider departing on Wednesday evenings when fares are most often at their lowest. Saturday 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 February 20, 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
8.1
Very good
4,411 reviews

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Frontier
6.0
Okay
3,355 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 1 outbound flight to Chicago Midway per day.

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

    Currently priced at $200, 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 Delta - these airlines can fly you to your destination from $207 and $262, respectively.

  • 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 $99 on Delta. Other airlines that offer cheap prices include Frontier from $104 and Southwest from $119 one-way.

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

    On average you can expect to pay $325 for a flight from Philadelphia to Chicago Midway Airport. The cheapest flight overall is $98 while the most popular route, (Philadelphia - Chicago Midway) is currently priced at $114.

  • 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Philadelphia to Midway

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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$55Average$138FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$158Average$272FlexibilityNo cancel feeOn-time63%
DeltaCheapest$186Average$310FlexibilityNo cancel feeOn-timeN/A
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