MDW - PHL

$87 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 4/27. 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
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
$159
Overall average: $275
Multiple Airlines
Thu 4/30Tue 5/5
MDW - PHL • 1 stop
Cheapest non-stop
$180
Typical prices: $176-$335
Southwest
Thu 4/16Sat 4/18
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 $160 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 1h 55m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 25% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 54% 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 Philadelphia!
Flight Deals
Booking Insights
Expert advice
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

Thu, Apr 30 - Tue, May 5
Multiple Airlines Logo
2:15 pm - 9:57 pm
MDW
-
PHL
6h 42m
1 stop
Multiple Airlines Logo
9:17 am - 7:31 pm
PHL
-
MDW
11h 14m
1 stop
$159Multiple Airlines
Thu, Apr 16 - Mon, Apr 20
Frontier Logo
6:00 am - 5:49 pm
MDW
-
PHL
10h 49m
1 stop
Frontier Logo
3:41 pm - 10:21 pm
PHL
-
MDW
7h 40m
1 stop
$160Frontier
Tue, Apr 21 - Thu, Apr 23
Frontier Logo
6:10 am - 1:18 pm
MDW
-
PHL
6h 08m
1 stop
Frontier Logo
10:38 pm - 5:54 pm
PHL
-
MDW
20h 16m
1 stop
$162Frontier
Tue, Apr 14 - Sat, Apr 18
Frontier Logo
6:10 am - 12:52 pm
MDW
-
PHL
5h 42m
1 stop
Frontier Logo
4:42 pm - 7:59 am
PHL
-
MDW
16h 17m
1 stop
$169Frontier
Thu, Apr 23 - Thu, Apr 30
Frontier Logo
6:00 am - 5:49 pm
MDW
-
PHL
10h 49m
1 stop
Frontier Logo
10:38 pm - 10:28 am
PHL
-
MDW
12h 50m
1 stop
$171Frontier
Thu, Apr 23 - Thu, Apr 30
Frontier Logo
6:00 am - 5:49 pm
MDW
-
PHL
10h 49m
1 stop
Frontier Logo
10:38 pm - 10:28 am
PHL
-
MDW
12h 50m
1 stop
$172Frontier
Thu, May 28 - Tue, Aug 4
Frontier Logo
8:05 am - 2:36 pm
MDW
-
PHL
5h 31m
1 stop
Frontier Logo
1:43 pm - 8:06 pm
PHL
-
MDW
7h 23m
1 stop
$175Frontier
Mon, Apr 20 - Wed, Apr 22
Frontier Logo
9:14 am - 10:38 am
MDW
-
PHL
24h 24m
1 stop
Frontier Logo
11:02 am - 7:31 pm
PHL
-
MDW
9h 29m
1 stop
$179Frontier
Thu, Apr 16 - Sat, Apr 18
Southwest Logo
3:25 pm - 6:25 pm
MDW
-
PHL
2h 00mnonstop
Southwest Logo
3:45 pm - 5:00 pm
PHL
-
MDW
2h 15mnonstop
$180Southwest
Fri, Apr 24 - Mon, Apr 27
Frontier Logo
6:49 pm - 7:41 am
MDW
-
PHL
11h 52m
1 stop
Frontier Logo
9:17 am - 7:31 pm
PHL
-
MDW
11h 14m
1 stop
$181Frontier
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.

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 Monday, 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 Mondays 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 $120 (return) on average. On the other hand, the most expensive months are February and July, where the average cost of round-trip tickets is $461 and $387 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.

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 $329 on average.

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 2 weeks before departure, which saves you about 25% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

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$87
Best time to beat the crowds with an average 36% drop 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 $87 for a one-way ticket and $159 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 737-800 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 $326 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 $158 and an overall rating of 5.7.

  • 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 $208 or less one-way and $287 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.
8.0
SouthwestOverall score based on 4317 reviews
8.1Boarding
8.0Comfort
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

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.

Frontier line changes my flight schedule with out my authorization. They never ask me and with out my concern they cut off 4 hours of my vacation they force my to leave 4 hours early from Puerto Rico.

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 Midway to Philadelphia

Information on your arrival and departure airports