PHL - MDW

$69 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 2/18. 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, 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
$128
Overall average: $344
Frontier
Wed 2/18Tue 2/24
PHL - MDW • 1 stop
Cheapest non-stop
$217
Typical prices: $341-$415
Southwest
Sat 3/14Tue 3/17
PHL - MDW • Non-stop
Our travelers' advice
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 $128 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 32% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
November
Cheapest • 27% price drop
April
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Midway!
Flight Deals
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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, Feb 18 - Tue, Feb 24
Frontier Logo
12:21 pm - 1:56 pm
PHL
-
MDW
26h 35m
1 stop
Frontier Logo
6:10 am - 5:12 pm
MDW
-
PHL
10h 02m
1 stop
$128Frontier
Mon, Feb 23 - Tue, Feb 24
Frontier Logo
12:28 pm - 10:29 pm
PHL
-
MDW
11h 01m
1 stop
Frontier Logo
6:10 am - 5:12 pm
MDW
-
PHL
10h 02m
1 stop
$144Frontier
Mon, Feb 9 - Thu, Feb 12
Frontier Logo
5:30 am - 11:45 am
PHL
-
MDW
7h 15m
1 stop
Frontier Logo
6:25 am - 6:11 pm
MDW
-
PHL
10h 46m
1 stop
$160Frontier
Wed, Mar 4 - Sat, Mar 7
Frontier Logo
11:40 am - 7:07 pm
PHL
-
MDW
8h 27m
1 stop
Frontier Logo
6:00 am - 1:24 am
MDW
-
PHL
18h 24m
1 stop
$163Frontier
Mon, Mar 2 - Wed, Mar 18
Frontier Logo
12:38 pm - 7:47 pm
PHL
-
MDW
8h 09m
1 stop
Frontier Logo
11:19 am - 7:16 pm
MDW
-
PHL
6h 57m
1 stop
$175Frontier
Fri, Feb 20 - Tue, Feb 24
Frontier Logo
12:28 pm - 10:25 pm
PHL
-
MDW
10h 57m
1 stop
Frontier Logo
6:10 am - 5:12 pm
MDW
-
PHL
10h 02m
1 stop
$179Frontier
Thu, Feb 5 - Wed, Feb 11
Frontier Logo
5:30 am - 11:45 am
PHL
-
MDW
7h 15m
1 stop
Frontier Logo
6:15 am - 5:12 pm
MDW
-
PHL
9h 57m
1 stop
$181Frontier
Tue, Mar 10 - Tue, Mar 17
Frontier Logo
11:52 am - 8:54 pm
PHL
-
MDW
10h 02m
1 stop
Frontier Logo
11:19 am - 7:16 pm
MDW
-
PHL
6h 57m
1 stop
$190Frontier
Mon, Feb 23 - Fri, Feb 27
Frontier Logo
12:28 pm - 7:47 pm
PHL
-
MDW
8h 19m
1 stop
Frontier Logo
7:53 pm - 6:11 pm
MDW
-
PHL
21h 18m
1 stop
$191Frontier
Wed, Feb 4 - Wed, Feb 11
Multiple Airlines Logo
7:04 pm - 11:45 am
PHL
-
MDW
17h 41m
1 stop
Multiple Airlines Logo
6:15 am - 11:50 pm
MDW
-
PHL
16h 35m
2 stops
$192Multiple Airlines
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 February, where the average cost of round-trip tickets is $388 and $344 respectively.

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 32% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 10 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 seasonJanuary
Cheapest flight$70
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 11% 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 $69 for a one-way ticket and $128 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 737-800 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 $318 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 $480 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 $198 or less one-way and $346 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 4268 reviews
7.5Entertainment
7.0Food
8.6Crew
8.1Boarding
8.0Comfort
Airline reviews

Great flight but super high price. Glad it was a business trip and not personal

10.0 ExcellentPieter, Jan 2026
LGB - DAL
Read more Southwest reviews

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

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

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

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.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

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