PHL - MDW

$102 Find Cheap Flights from Philadelphia to Chicago Midway Airport - Compare and Save

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 8/25. 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 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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Everything you should know

Cheapest round-trip
$204
Typical prices: $318-$172
Southwest
Wed 8/26Sat 8/29
PHL - MDW • Non-stop
Cheapest one-way
$102
Typical prices: $98-$229
Southwest
Tue 8/25
PHL - MDW • 1 stop
Top airlines
Cheapest • from $204 (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 2h 10m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Most punctual • 79% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $266 (round-trip)
Shortest trip • 3h 57m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 30% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 33% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Philadelphia to Midway (PHL-MDW)

 
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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Philadelphia to Midway

Wed, Aug 26 - Sat, Aug 29
Southwest Logo
10:45 am - 11:55 am
PHL
-
MDW
2h 10mnonstop
Southwest Logo
8:10 am - 11:15 am
MDW
-
PHL
2h 05mnonstop
$204Southwest
Wed, Aug 5 - Wed, Aug 12
Delta Logo
5:15 am - 9:59 am
PHL
-
MDW
5h 44m
1 stop
Delta Logo
1:27 pm - 7:25 pm
MDW
-
PHL
4h 58m
1 stop
$205Delta
Wed, Aug 26 - Wed, Sep 2
Southwest Logo
7:15 am - 3:25 pm
PHL
-
MDW
9h 10m
2 stops
Southwest Logo
2:00 pm - 9:50 pm
MDW
-
PHL
6h 50m
1 stop
$210Southwest
Wed, Aug 26 - Sat, Aug 29
Southwest Logo
7:55 am - 8:55 am
PHL
-
MDW
2h 00mnonstop
Southwest Logo
6:35 am - 1:25 pm
MDW
-
PHL
5h 50m
1 stop
$214Southwest
Wed, Aug 26 - Wed, Sep 2
Southwest Logo
7:15 am - 3:50 pm
PHL
-
MDW
9h 35m
2 stops
Southwest Logo
12:35 pm - 9:50 pm
MDW
-
PHL
8h 15m
2 stops
$215Southwest
Tue, Jul 7 - Wed, Jul 8
Frontier Logo
4:30 pm - 10:03 pm
PHL
-
MDW
6h 33m
1 stop
Frontier Logo
12:11 pm - 10:28 pm
MDW
-
PHL
9h 17m
1 stop
$216Frontier
Tue, Jul 28 - Tue, Aug 4
Frontier Logo
4:30 pm - 10:03 pm
PHL
-
MDW
6h 33m
1 stop
Frontier Logo
12:11 pm - 10:28 pm
MDW
-
PHL
9h 17m
1 stop
$218Frontier
Wed, Aug 26 - Sat, Aug 29
Southwest Logo
7:15 am - 3:50 pm
PHL
-
MDW
9h 35m
2 stops
Southwest Logo
8:10 am - 11:15 am
MDW
-
PHL
2h 05mnonstop
$219Southwest
Thu, Aug 6 - Tue, Aug 11
Southwest Logo
12:45 pm - 1:45 pm
PHL
-
MDW
2h 00mnonstop
Southwest Logo
11:25 am - 2:20 pm
MDW
-
PHL
1h 55mnonstop
$223Southwest
Wed, Aug 5 - Mon, Aug 10
Delta Logo
5:15 am - 9:59 am
PHL
-
MDW
5h 44m
1 stop
Delta Logo
5:10 pm - 1:19 am
MDW
-
PHL
7h 09m
1 stop
$224Delta
Booking Insights

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.

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

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

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, Friday 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 Thursday, with Tuesday 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 November, where tickets cost $206 (return) on average. On the other hand, the most expensive months are March and June, where the average cost of round-trip tickets is $461 and $378 respectively.

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

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 $337, prices are generally cheapest when you fly direct.

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 2 weeks before departure, which saves you about 30% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Expert advice

Expert advice for your flight from Philadelphia to Midway

 
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 seasonFebruary
Cheapest flight$102
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 24% 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 5 days, the lowest price for a flight from Philadelphia to Chicago Midway Airport was $102 for a one-way ticket and $204 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, 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 MAX 8 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 Frontier?

    The two airlines most popular with KAYAK users for flights from Philadelphia to Chicago are Southwest and Frontier. With an average price for the route of $335 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 $167 and an overall rating of 5.6.

  • 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 $195 or less one-way and $357 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?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Philadelphia to Chicago Midway.
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

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

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

Reviews of the top airlines flying 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.
7.9
SouthwestOverall score based on 4235 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

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.

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

Other airlines flying to Philadelphia

Flight deals from the most popular airlines with KAYAK users flying the route