PHL - MDW

$77 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 4/23. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$166
Overall average: $241
Frontier
Fri 4/17Tue 4/21
PHL - MDW • 1 stop
Cheapest non-stop
$180
Typical prices: $194-$338
Southwest
Wed 4/15Sat 4/18
PHL - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest offers two free checked bags, ideal for luggage.
Use the CTA Orange Line from MDW for quick downtown access.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Frontier
Cheapest • from $166 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 13m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Southwest
Most punctual • 79% on-time
Morning flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 45% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
November
Cheapest • 28% price drop
April
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

Fri, Apr 17 - Tue, Apr 21
Frontier Logo
10:38 pm - 4:00 pm
PHL
-
MDW
18h 22m
1 stop
Frontier Logo
6:10 am - 1:18 pm
MDW
-
PHL
6h 08m
1 stop
$166Frontier
Thu, Apr 16 - Wed, Apr 22
Frontier Logo
3:41 pm - 10:22 pm
PHL
-
MDW
7h 41m
1 stop
Frontier Logo
2:15 pm - 12:54 am
MDW
-
PHL
9h 39m
1 stop
$170Frontier
Thu, May 14 - Sun, May 17
Frontier Logo
10:38 pm - 8:04 am
PHL
-
MDW
10h 26m
1 stop
Frontier Logo
9:14 am - 7:41 am
MDW
-
PHL
21h 27m
1 stop
$171Frontier
Wed, May 6 - Sat, May 9
Multiple Airlines Logo
9:17 am - 10:19 pm
PHL
-
MDW
14h 02m
1 stop
Multiple Airlines Logo
6:00 am - 11:10 pm
MDW
-
PHL
16h 10m
2 stops
$173Multiple Airlines
Mon, Apr 20 - Mon, Apr 27
Frontier Logo
7:24 pm - 7:31 pm
PHL
-
MDW
25h 07m
2 stops
Frontier Logo
2:15 pm - 9:11 am
MDW
-
PHL
17h 56m
1 stop
$174Frontier
Tue, Apr 7 - Tue, Apr 14
Multiple Airlines Logo
6:48 am - 10:19 pm
PHL
-
MDW
16h 31m
2 stops
Multiple Airlines Logo
2:15 pm - 12:54 am
MDW
-
PHL
9h 39m
1 stop
$176Multiple Airlines
Thu, Apr 23 - Sun, Apr 26
Frontier Logo
11:58 am - 7:31 pm
PHL
-
MDW
8h 33m
1 stop
Frontier Logo
6:00 am - 8:10 am
MDW
-
PHL
25h 10m
1 stop
$177Frontier
Thu, Apr 23 - Fri, Apr 24
Frontier Logo
11:58 am - 10:19 pm
PHL
-
MDW
11h 21m
1 stop
Frontier Logo
6:49 pm - 7:41 am
MDW
-
PHL
11h 52m
1 stop
$179Frontier
Tue, Apr 21 - Sat, Apr 25
Southwest Logo
5:45 pm - 6:55 pm
PHL
-
MDW
2h 10mnonstop
Southwest Logo
7:40 am - 10:35 am
MDW
-
PHL
1h 55mnonstop
$180Southwest
Mon, Apr 27 - Wed, May 6
Frontier Logo
9:17 am - 7:31 pm
PHL
-
MDW
11h 14m
1 stop
Frontier Logo
2:20 pm - 12:54 am
MDW
-
PHL
9h 34m
1 stop
$181Frontier
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.

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 Monday is the most expensive. Flying from Chicago Midway Airport back to Philadelphia, the best deals are generally found on Monday, 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 $202 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $461 and $335 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $360 on average.

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 45% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 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$77
Best time to beat the crowds but there is an average 17% increase in price.
Most popular time to fly and prices are also 14% 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 $77 for a one-way ticket and $166 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, JetBlue, and Alaska Airlines 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.

  • Which airline alliances offer flights from Philadelphia to Chicago Midway Airport?

    Star Alliance is the only airline alliance operating flights between Philadelphia and Chicago Midway Airport.

  • 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 United Airlines?

    The two airlines most popular with KAYAK users for flights from Philadelphia to Chicago are Southwest and United Airlines. With an average price for the route of $311 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $461 and an overall rating of 7.4.

  • 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 $203 or less one-way and $359 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 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 4315 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

First of all we hade waited 3 hours in the airplane waiting to leave. Second the return schedule was changed and it messed up my entire vaction. I won't buy never again another flight and recommend to nobody traveling with them.

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

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