MDW - PHL

$91 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 6/2. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$185
Typical prices: $342-$218
Frontier
Wed 6/3Wed 6/3
MDW - PHL • 1 stop
Cheapest non-stop
$247
Typical prices: $417-$244
Southwest
Sun 5/24Wed 5/27
MDW - PHL • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest's two free checked bags benefit luggage needs.
Midway's compact terminal eases navigation and access.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $185 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 1h 58m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
When to travel
Cheapest • 60% price drop
Most popular
Good to know
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+1
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Flight 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

Wed, Jun 3 - Wed, Jun 3
Frontier Logo
6:00 am - 12:25 pm
MDW
-
PHL
5h 25m
1 stop
Frontier Logo
4:25 pm - 10:02 pm
PHL
-
MDW
6h 37m
1 stop
$185Frontier
Tue, Jun 2 - Tue, Jun 9
Frontier Logo
12:27 pm - 7:10 pm
MDW
-
PHL
5h 43m
1 stop
Frontier Logo
4:35 pm - 10:11 pm
PHL
-
MDW
6h 36m
1 stop
$188Frontier
Wed, Jun 3 - Tue, Jun 9
Frontier Logo
12:04 pm - 7:10 pm
MDW
-
PHL
6h 06m
1 stop
Frontier Logo
4:35 pm - 10:11 pm
PHL
-
MDW
6h 36m
1 stop
$190Frontier
Tue, Jun 2 - Wed, Jun 3
Frontier Logo
6:00 am - 12:25 pm
MDW
-
PHL
5h 25m
1 stop
Frontier Logo
6:30 am - 11:09 am
PHL
-
MDW
5h 39m
1 stop
$195Frontier
Wed, May 27 - Tue, Jun 2
Frontier Logo
12:04 pm - 10:10 pm
MDW
-
PHL
9h 06m
1 stop
Frontier Logo
4:25 pm - 10:02 pm
PHL
-
MDW
6h 37m
1 stop
$200Frontier
Thu, May 28 - Tue, Jun 2
Frontier Logo
6:00 am - 12:25 pm
MDW
-
PHL
5h 25m
1 stop
Frontier Logo
6:30 am - 11:12 am
PHL
-
MDW
5h 42m
1 stop
$201Frontier
Wed, May 27 - Sat, May 30
Frontier Logo
6:00 am - 12:25 pm
MDW
-
PHL
5h 25m
1 stop
Frontier Logo
6:30 am - 11:04 am
PHL
-
MDW
5h 34m
1 stop
$202Frontier
Wed, Jun 3 - Mon, Jun 8
Frontier Logo
6:00 am - 7:10 pm
MDW
-
PHL
12h 10m
1 stop
Frontier Logo
4:25 pm - 10:02 pm
PHL
-
MDW
6h 37m
1 stop
$204Frontier
Mon, Jun 1 - Tue, Jun 2
Frontier Logo
12:04 pm - 7:14 pm
MDW
-
PHL
6h 10m
1 stop
Frontier Logo
4:25 pm - 10:02 pm
PHL
-
MDW
6h 37m
1 stop
$208Frontier
Wed, Jun 3 - Sun, Jun 7
Frontier Logo
12:04 pm - 7:10 pm
MDW
-
PHL
6h 06m
1 stop
Frontier Logo
6:30 am - 11:12 am
PHL
-
MDW
5h 42m
1 stop
$210Frontier
Booking Insights

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.

How much is a round-trip flight from Chicago Midway Airport to Philadelphia?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Philadelphia departing in June.

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 Thursday, 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 October, where tickets cost $116 (return) on average. On the other hand, the most expensive months are February and April, where the average cost of round-trip tickets is $461 and $442 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to Philadelphia?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $357, prices are generally cheapest when you fly direct.

Expert advice

Expert advice for your flight from Midway to Philadelphia

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Blane Bachelor

Blane Bachelor

Expert on Southwest

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.

Stefanie Waldek

Stefanie Waldek

Expert on Frontier and MDW

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.

Harriet Baskas

Harriet Baskas

Expert on PHL

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.

Good to know

Low seasonJanuary
Cheapest flight$91
Best time to beat the crowds with an average 42% drop in price.
Most popular time to fly with an average 52% increase in price.
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 $91 for a one-way ticket and $185 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 JetBlue 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 MAX 8 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 $364 and an overall rating of 7.9, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $160 and an overall rating of 5.6.

  • 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 $163 or less one-way and $325 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

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Philadelphia to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

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.
7.9
SouthwestOverall score based on 4296 reviews
8.6Crew
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
Airline reviews

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

2.0 MediocreAnonymous, May 2026
MCO - MDW
Read more Southwest reviews

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

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

Information on your arrival and departure airports