PHL - MDW

$54 Find Cheap Flights from Philadelphia to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Philadelphia to Midway departing on 6/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Philadelphia to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Philadelphia to Chicago, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Philadelphia to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Philadelphia to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Philadelphia to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Philadelphia to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
10:38 pm - 11:51 pmPHL-MDW
2h 13mnonstop
Frontier Logo
6:40 pm - 9:45 pmMDW-PHL
2h 05mnonstop
$100Frontier
Find Deal
Mon, Jul 7 - Fri, Jul 11
Frontier Logo
6:35 pm - 7:52 pmPHL-MDW
2h 17mnonstop
Frontier Logo
8:52 pm - 11:56 pmMDW-PHL
2h 04mnonstop
$110Frontier
Find Deal
Fri, Jun 6 - Mon, Jun 9
Frontier Logo
6:39 pm - 7:55 pmPHL-MDW
2h 16mnonstop
Frontier Logo
8:55 pm - 11:59 pmMDW-PHL
2h 04mnonstop
$112Frontier
Find Deal
Mon, May 26 - Fri, May 30
Frontier Logo
6:39 pm - 7:55 pmPHL-MDW
2h 16mnonstop
Frontier Logo
8:52 pm - 11:56 pmMDW-PHL
2h 04mnonstop
$113Frontier
Find Deal
Fri, May 30 - Mon, Jun 2
Southwest Logo
5:55 am - 7:00 amPHL-MDW
2h 05mnonstop
Southwest Logo
6:30 am - 9:25 amMDW-PHL
1h 55mnonstop
$161Southwest
Find Deal
Wed, Jul 2 - Thu, Jul 3
Southwest Logo
5:55 am - 7:00 amPHL-MDW
2h 05mnonstop
Southwest Logo
5:20 pm - 11:35 pmMDW-PHL
5h 15m1 stop
$171Southwest
Find Deal
Wed, Jul 2 - Thu, Jul 3
Southwest Logo
12:15 pm - 1:20 pmPHL-MDW
2h 05mnonstop
Southwest Logo
1:00 pm - 3:55 pmMDW-PHL
1h 55mnonstop
$177Southwest
Find Deal
Wed, May 28 - Wed, Jun 4
Delta Logo
6:00 am - 8:41 amPHL-MDW
3h 41m1 stop
Delta Logo
4:26 pm - 12:59 amMDW-PHL
7h 33m1 stop
$197Delta
Find Deal
Thu, Jul 3 - Sat, Jul 5
Delta Logo
5:30 am - 9:40 amPHL-MDW
5h 10m1 stop
Delta Logo
12:48 pm - 8:55 pmMDW-PHL
7h 07m1 stop
$208Delta
Find Deal
Wed, May 21 - Sat, May 24
Delta Logo
6:00 am - 8:40 amPHL-MDW
3h 40m1 stop
Delta Logo
6:00 am - 12:10 pmMDW-PHL
5h 10m1 stop
$217Delta
Find Deal
Sat, May 24 - Sun, Jun 1
Expert advice

Expert advice for your flight from Philadelphia to Midway

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-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.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Frontier

Frontier's Economy Bundle includes a carry-on bag and seat choice, offering budget-friendly flexibility.


Pay for bags early online to save money; airport fees are higher.

Read more about Frontierby Stefanie Waldek
Southwest

Enjoy two free checked bags up to 50 pounds each, ideal for travelers with extra luggage.


Set an alarm to check in 24 hours before for a better boarding position.

Read more about Southwestby Blane Bachelor
Airports
PHL

SEPTA runs trains from PHL to Center City daily. Save money by purchasing a Quick Trip or SEPTA Key card before boarding.

Read more about PHLby Harriet Baskas
MDW

Take the CTA Orange Line from MDW to downtown Chicago in about 25-30 minutes. It's a short walk from the terminal.

Read more about MDWby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier and MDW

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more
Harriet Baskas

Harriet Baskas

Expert on PHL

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Useful Info

KAYAK's insights & trends for Philadelphia to Midway flights

Get data-powered insights and trends into flights from Philadelphia to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Philadelphia to Chicago Midway Airport?

The average price of all round-trip flights from Philadelphia to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

For Philadelphia to Chicago Midway Airport, Saturday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago Midway Airport back to Philadelphia, the best deals are generally found on Saturday, with Monday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Philadelphia to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Philadelphia to Chicago Midway Airport is August, where tickets cost $138 (return) on average. On the other hand, the most expensive months are March and February, where the average cost of round-trip tickets is $381 and $335 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Philadelphia to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Philadelphia to Chicago Midway Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low seasonJanuary
High seasonOctober
Cheapest flight$54
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Philadelphia to Chicago Midway Airport

When to book flights from Philadelphia to Midway

Are your dates flexible? Find out the best times to travel from Philadelphia to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Philadelphia to Chicago Midway Airport flights

  • For flights from Philadelphia to Chicago Midway International Airport, which airlines have liberal baggage policies?

    For flights leaving from Philadelphia to MDW Airport, several carriers, most notably Delta Air Lines, American Airlines, and United Airlines, have loosened their baggage restrictions. Customers of these airlines are not charged for carry-on bags weighing less than than 22 pounds. Additionally, these carriers offer discounted pricing for checked baggage weighing no more than 50 pounds. These airlines charge less per pound of extra checked luggage than other airlines that fly this route.

  • Which airlines fly to Chicago Midway International Airport (MDW) from Philadelphia (PHL) and accept pets?

    Pets are welcome on board most flights operated by different airlines between Philadelphia and Chicago Midway Airport, provided that the pet carrier fits underneath the seats. Make sure the pet's total weight, including that of the carrier, is less than the 25-lbs limit. Pet-friendly airlines include American Airlines, Delta Air Lines, United Airlines, and British Airways.

  • Which route offers the cheapest flights from Philadelphia (PHL) to Chicago Midway Airport (MDW)?

    Travelers on a tight budget may find it more cost-effective to take a connecting flight from Philadelphia to Chicago Midway Airport than a direct one. Several airlines, like United Airlines, Delta, Southwest Airlines, and American Airlines, operate connecting flights on this route. These airlines' main layover cities are Houston, Detroit, Baltimore, and Dallas, in that order.

  • Which mode of transportation will get you to Philadelphia International Airport from central Philadelphia for the least amount of money?

    SEPTA runs a regional railway known as the Airport Line, offering direct transportation from Center City Philadelphia to PHL Airport. This alternative is typically the most economical, as the cost of one-way tickets is notably lower compared to other means of transportation.

  • What is the cheapest flight from Philadelphia to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Philadelphia to Chicago Midway Airport was $54 for a one-way ticket and $100 for a round-trip.

  • Do I need a passport to fly between Philadelphia and Chicago Midway Airport?

    A passport is not required to fly from Philadelphia to Chicago Midway Airport.

  • Which airports will I be using when flying from Philadelphia to Chicago Midway Airport?

    When flying out of Philadelphia you will be using Philadelphia. You will be landing at Chicago Midway Airport, also known as Chicago Midway.

  • Which airlines offer Wi-Fi service onboard planes from Philadelphia to Chicago Midway Airport?

    American Airlines, Delta, Alaska Airlines, and JetBlue offer inflight Wi-Fi service on the Philadelphia to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Philadelphia to Chicago Midway Airport?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Philadelphia to Chicago Midway Airport flight route.

  • On which days can I fly direct from Philadelphia to Chicago Midway Airport?

    There are nonstop flights from Philadelphia to Chicago Midway Airport on a daily basis.

  • Which is the best airline for flights from Philadelphia to Chicago, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Philadelphia to Chicago are Southwest and Delta. With an average price for the route of $298 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $310 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Philadelphia to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Philadelphia to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Philadelphia to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Philadelphia is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Philadelphia to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Philadelphia with another airline. Booking your flights between Philadelphia and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Philadelphia to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Philadelphia up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Philadelphia to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $134 or less one-way and $218 or less round-trip.
  • Corporate travelers from Philadelphia (PHL) to Chicago frequently use Chicago Midway International Airport (MDW) as their arrival point. This is because Midway Airport is situated just 10 miles southwest of downtown Chicago, making it more convenient for business travelers who have meetings or conferences in the city. Its proximity to the downtown area reduces travel time and allows for easier access to corporate offices and other business destinations.
  • Consider flying with Frontier Airlines, Delta, or United Airlines if you want to take advantage of the option of upgrading to first class on your flight from Philadelphia to MDW Airport. When checking in or buying a ticket, these airlines give customers the option to use a bidding system to ask for an upgrade from the economy or business classes.
  • If you are looking for entertainment options on your flight from Philadelphia (PHL) to Chicago Midway Airport (MDW), think about flying with United Airways, Delta, or American Airlines. By selecting one of these airlines, travelers can enjoy free Wi-Fi on board in order to enjoy some of their favorite TV shows, cartoon networks for kids, or music.
  • The majority of environmentally aware travelers choose to depart from Philadelphia International Airport (PHL) when traveling from Philadelphia to Chicago Midway Airport. This is because PHL Airport has decreased its dependence on fossil fuels by adopting renewable energy sources, specifically solar power. PHL relies more heavily on solar panels to generate electricity, resulting in a more sustainable and eco-friendly energy supply.
  • If you plan to catch a morning flight from Philadelphia to MDW Airport, it's worth considering staying overnight close to PHL Airport. The Philadelphia Airport Marriott is an appropriate option for accommodation, because it is located in the airport with its own security gate. Furthermore, guests can enjoy a complimentary breakfast at this hotel.

Prefer to fly direct from Philadelphia to Chicago Midway Airport?

Find which airlines fly direct from Philadelphia Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Philadelphia to Chicago Midway

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Philadelphia

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

Top 3 airlines serving from Philadelphia to Midway

 
See real verified KAYAK customer reviews for airlines flying from Philadelphia to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Philadelphia to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4294 reviews
8.2Boarding
7.6Entertainment
8.6Crew
8.0Comfort
7.1Food
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

Everything you need to know for your flight from Philadelphia to Midway

Information on your arrival and departure airports

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