MDW - PHL

$48 Find Cheap Flights from Chicago Midway Airport to Philadelphia

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Philadelphia departing on 9/18. 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
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Philadelphia

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

Cheap Flights from Midway to Philadelphia (MDW-PHL)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Philadelphia 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Philadelphia

Thu, Sep 18 - Mon, Sep 22
Frontier Logo
8:15 am - 11:16 amMDW-PHL
2h 01mnonstop
Frontier Logo
6:05 am - 7:16 amPHL-MDW
2h 11mnonstop
$97Frontier
Find Deal
Thu, Sep 11 - Mon, Sep 15
Frontier Logo
8:15 am - 11:16 amMDW-PHL
2h 01mnonstop
Frontier Logo
6:05 am - 7:16 amPHL-MDW
2h 11mnonstop
$98Frontier
Find Deal
Mon, Aug 18 - Mon, Aug 18
Frontier Logo
6:00 am - 4:48 pmMDW-PHL
9h 48m1 stop
Frontier Logo
10:38 pm - 11:51 pmPHL-MDW
2h 13mnonstop
$102Frontier
Find Deal
Thu, Sep 4 - Sun, Sep 7
Frontier Logo
8:15 am - 11:16 amMDW-PHL
2h 01mnonstop
Frontier Logo
5:01 am - 12:44 pmPHL-MDW
8h 43m1 stop
$107Frontier
Find Deal
Thu, Aug 21 - Sun, Aug 24
Frontier Logo
2:05 pm - 5:15 pmMDW-PHL
2h 10mnonstop
Frontier Logo
1:28 pm - 2:41 pmPHL-MDW
2h 13mnonstop
$108Frontier
Find Deal
Fri, Aug 15 - Mon, Aug 18
Frontier Logo
6:40 pm - 9:45 pmMDW-PHL
2h 05mnonstop
Frontier Logo
10:38 pm - 11:51 pmPHL-MDW
2h 13mnonstop
$109Frontier
Find Deal
Fri, Aug 1 - Mon, Aug 4
Frontier Logo
6:40 pm - 9:45 pmMDW-PHL
2h 05mnonstop
Frontier Logo
10:38 pm - 11:51 pmPHL-MDW
2h 13mnonstop
$110Frontier
Find Deal
Wed, Aug 20 - Sat, Aug 23
Frontier Logo
8:00 am - 4:30 pmMDW-PHL
7h 30m1 stop
Frontier Logo
6:25 pm - 11:08 pmPHL-MDW
5h 43m1 stop
$111Frontier
Find Deal
Sat, Aug 2 - Sat, Aug 9
Southwest Logo
7:05 pm - 10:00 pmMDW-PHL
1h 55mnonstop
Southwest Logo
5:25 pm - 6:35 pmPHL-MDW
2h 10mnonstop
$141Southwest
Find Deal
Sat, Aug 2 - Sun, Aug 24
Southwest Logo
6:30 am - 9:25 amMDW-PHL
1h 55mnonstop
Southwest Logo
5:30 am - 6:30 amPHL-MDW
2h 00mnonstop
$159Southwest
Find Deal
Expert advice

Expert advice for your flight from Midway to Philadelphia

 
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 Standard seat choice, offering budget-friendly options.


Frontier's Premium Bundle offers priority boarding and extra legroom seats for just $20 more.

Read more about Frontierby Stefanie Waldek
Southwest

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


Southwest's Rapid Rewards program offers unlimited rewards seats and points that never expire.

Read more about Southwestby Blane Bachelor
Airports
MDW

Midway offers a compact terminal with three concourses, making it easy to navigate and access dining and shopping options quickly.

Read more about MDWby Stefanie Waldek
PHL

Take the SEPTA Airport Line from PHL to Center City for an affordable 30-minute ride to downtown Philadelphia.

Read more about PHLby Harriet Baskas
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 Midway to Philadelphia flights

Get data-powered insights and trends into flights from Midway to Philadelphia 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 Chicago Midway Airport to Philadelphia?

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

If your flying dates are flexible, you should consider flying to Philadelphia on a Saturday, as we generally find the cheapest rates on that day for this route. On the other hand, Tuesday is the most expensive day to fly from Chicago Midway Airport to Philadelphia. For your return ticket, we recommend flying on a Friday and avoiding Sundays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Philadelphia, 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 Chicago Midway Airport to Philadelphia is September, where tickets cost $81 (return) on average. On the other hand, the most expensive months are February and March, where the average cost of round-trip tickets is $290 and $287 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to Philadelphia, 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 Chicago Midway Airport to Philadelphia, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$48
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 32% lower on average.
Flight from Chicago Midway Airport to Philadelphia

When to book flights from Midway to Philadelphia

Are your dates flexible? Find out the best times to travel from Midway to Philadelphia 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 Chicago Midway Airport to Philadelphia flights

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Philadelphia was $48 for a one-way ticket and $97 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

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

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

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to Philadelphia are Southwest and Frontier. With an average price for the route of $288 and an overall rating of 8.0, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $138 and an overall rating of 5.9.

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

    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 Chicago Midway Airport to Philadelphia.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Philadelphia from Chicago Midway Airport 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 Chicago Midway Airport to Philadelphia?

    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 Philadelphia with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and PHL 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 Chicago Midway Airport to Philadelphia?

    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 Philadelphia from Chicago Midway Airport 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 Chicago Midway Airport to Philadelphia

  • Looking for a cheap flight? 25% of our users found flights on this route for $94 or less one-way and $155 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Philadelphia?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Philadelphia.
Find which airlines fly direct from Chicago Midway Airport to Philadelphia Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Philadelphia

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Frontier, Southwest

Frontier, Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Southwest

Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights

Direct returns

Philadelphia to Chicago Midway

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Frontier, Southwest

Frontier, Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Southwest

Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights

Reviews of the top airlines flying from Midway to Philadelphia

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Philadelphia. 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 Midway to Philadelphia? 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 4266 reviews
8.0Comfort
7.0Food
8.6Crew
8.2Boarding
7.6Entertainment
Airline reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

4.0 OkayTraci, Jun 2025OAK - SEA
Read more Southwest reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

We’ve all seen the YouTube vids of out of control passengers. But this was an instance of a highly aggressive, bully flight attendant. Yelling in the face of a vet with PTSD who was texting their family. And no , we had not yet been instructed to put our phones in airplane mode. My suggestion is that you should pay whatever difference there is in order to avoid Frontier airlines. Additionally, after 3hrs trying to get customer service frontier offered a $25 voucher. I declined. This experience was so traumatic. To be verbally assaulted and abused by a flight attendant that has the power to say “boo” and I miss my flight ( which was to a family member’s funeral ). Frontier is unsafe and I cannot impress enough how much I discourage anyone ( esp those with any kind of disability like PTSD ) flying on Frontier.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

We were delayed three times ,and that destroyed my plans, and reservations

Very bad! No good service delayed my second connection flight

The confirmation # CK8GNW and my name was not recognized/in Frontier system. I was able to check in on Frintier app so i went to the Frontier ticket agent, at time they told me that my name/ confirmation did not show up as a purchased ticket. I had to purchase a new ticket that cost $289.00 one way.

Flight was late. Missed connecting in Denver. My new flight is more than 24 hours later and I have no room, vouchers, or compensation, and might also be bumped from the one tomorrow.

Frontier is terrible. Paid for exit row, not given exit row, refused to refund fee.

2 hour delay due to late plane, wrong size plane causing overbooking, and people getting off and on the plane after boarding was completed.

We had to wait in line over an hour just to check our bags. It's a good thing we were so early to the airport. Only one clerk was working and the line was around the corner and down the hall. No good. I felt bad for her. Not sure how she kept her sanity with all the upset people. Then we get to our gate and there is no seating. Everyone was standing. Then I realize it is not a gate at all, we still have to be shuttled to our airplane. Ugh. Then we were late taking off and missed a window of opportunity before the airport runways were shut down for some reason. (not frontier's fault the runway shut down.) The seats on the airline are crammed and there is no cushion. Never had a tighter seating arrangement while flying. My 6' 4" husband was absolutely miserable the whole time with knees digging in to the seat in front of him. You think you are getting a good deal on a ticket, and then wham! I had to pay 75 dollars for our checked bags and 75 dollars for a carry on. No other airline does that!!! And also, there is a 40 pound weight limit on checked bags... Would have been cheaper flying with another airline, and I would have at least gotten a snack and drink. Was thankful for the tiny cup of water at least.

This was one of the first frontier airline flights this spring that wasn't delayed. It actually left on time. Some of the flight crew did not look happy, they didn't smile when the passengers were boarding or getting off the plane, and the passengers initiated greetings, not the staff. To me this was an odd experience to have with any flight/airline. I had a bad experience booking this flight. The price didn't solidify until late hours into the night. Ever time I purchased the ticket, I either received a denial email or an error because the price has changed, but it was never reflected on the flyfrontier or kayak websites until way after midnight on the date of travel. This caused me anxiety and irritation with the websites. Then I noticed a mishap with my name on my voucher as I went to check in, it was incorrect. When I proceeded to correct it, Frontier had no easy, let alone free, way to remedy it. I couldn't correct my name without a $75 charge, I couldn't cancel my voucher to repurchase it with the correct name without a $100 charge, because it was too close to departure. Then calling frontier was nearly impossible to remedy the situation with a human. It's already difficult to want to choose frontier because of all the upcharges, but you feel kinda trapped into doing so because it's the more affordable airline.

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

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