$64 Find Cheap Flights from Chicago Midway Airport to Pennsylvania

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 Pennsylvania departing on 1/30. 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 Pennsylvania

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Pennsylvania, 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 Pennsylvania, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Midway to Pennsylvania

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Philadelphia
Philadelphia1 stop$128
Pittsburgh
Pittsburghnonstop$171
Harrisburg
Harrisburg2 stops$180
New York
Newarknonstop$104
Washington, D.C.
Baltimorenonstop$139
Philadelphia
Philadelphia1 stop$128
Pittsburgh
Pittsburghnonstop$171
Harrisburg
Harrisburg2 stops$180
New York
Newarknonstop$104
Washington, D.C.
Baltimorenonstop$139

Book Cheap Midway to Pennsylvania Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Pennsylvania 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 Pennsylvania

Tue, Jan 13 - Wed, Jan 28
Frontier Logo
6:30 pm - 9:30 pm
MDW
-
EWR
2h 00mnonstop
Frontier Logo
6:10 am - 12:05 pm
EWR
-
MDW
6h 55m1 stop
$104Frontier
Sun, Jan 18 - Thu, Jan 22
Frontier Logo
6:30 pm - 9:30 pm
MDW
-
EWR
2h 00mnonstop
Frontier Logo
6:00 am - 11:45 am
EWR
-
MDW
6h 45m1 stop
$115Frontier
Thu, Jan 15 - Thu, Jan 22
Frontier Logo
6:30 pm - 9:30 pm
MDW
-
EWR
2h 00mnonstop
Frontier Logo
6:00 am - 11:45 am
EWR
-
MDW
6h 45m1 stop
$117Frontier
Thu, Jan 15 - Sun, Jan 18
Multiple Airlines Logo
8:19 pm - 2:50 pm
MDW
-
EWR
17h 31m1 stop
Multiple Airlines Logo
10:30 pm - 12:02 am
EWR
-
MDW
2h 32mnonstop
$118Multiple Airlines
Tue, Jan 13 - Tue, Jan 20
Frontier Logo
6:30 pm - 9:30 pm
MDW
-
EWR
2h 00mnonstop
Frontier Logo
6:00 am - 12:05 pm
EWR
-
MDW
7h 05m1 stop
$121Frontier
Sat, Jan 17 - Sun, Jan 18
Southwest Logo
9:45 am - 12:40 pm
MDW
-
PHL
1h 55mnonstop
Southwest Logo
5:40 am - 7:00 am
PHL
-
MDW
2h 20mnonstop
$139Southwest
Tue, Jan 13 - Tue, Jan 20
Southwest Logo
5:55 pm - 9:00 pm
MDW
-
LGA
2h 05mnonstop
Southwest Logo
6:00 am - 7:40 am
LGA
-
MDW
2h 40mnonstop
$139Southwest
Wed, Jan 7 - Tue, Jan 13
Multiple Airlines Logo
3:01 pm - 4:49 pm
MDW
-
PHL
24h 48m1 stop
Multiple Airlines Logo
5:30 am - 10:34 am
PHL
-
MDW
6h 04m1 stop
$147Multiple Airlines
Thu, Jan 15 - Tue, Jan 20
Delta Logo
1:28 pm - 6:32 pm
MDW
-
PIT
4h 04m1 stop
Delta Logo
6:32 am - 1:09 pm
PIT
-
MDW
7h 37m1 stop
$191Delta
Sat, Jan 17 - Sun, Jan 18
Delta Logo
9:32 am - 1:27 pm
MDW
-
PIT
2h 55m1 stop
Delta Logo
2:09 pm - 5:34 pm
PIT
-
MDW
4h 25m1 stop
$223Delta
Booking Insights

KAYAK's insights & trends for Midway to Pennsylvania flights

Get data-powered insights and trends into flights from Midway to Pennsylvania to help you find the cheapest flights, the best time to fly and much more.

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

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

What is the cheapest Chicago Midway Airport to Pennsylvania flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Pennsylvania from Chicago Midway Airport found in the last 72 hours was to Philadelphia, at $120 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Philadelphia (PHL), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $120.

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

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 $311, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport to Pennsylvania?

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 Pennsylvania, 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 Pennsylvania is October, when tickets cost $120 (return) on average. On the other hand, the most expensive months are July and February, when the average cost of round-trip tickets is $337 and $298 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Pennsylvania?

The average price of all round-trip flights from Chicago Midway Airport to Pennsylvania clicked on KAYAK for each day over the last 12 months.

For Chicago Midway Airport to Pennsylvania, Monday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Pennsylvania back to Chicago Midway Airport, the best deals are generally found on Friday, with Monday being the most expensive.

How far in advance should I book a flight from Chicago Midway Airport to Pennsylvania?

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 Pennsylvania, 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 Pennsylvania, you should book around 2 weeks before departure, which saves you about 48% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$64
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 36% increase in price.
Flight from Chicago Midway Airport to Philadelphia

FAQs - booking Pennsylvania flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Pennsylvania?

    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 Pennsylvania.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Pennsylvania?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Pennsylvania 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 Pennsylvania?

    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 from Chicago Midway Airport to Pennsylvania with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Pennsylvania?

    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 from Chicago Midway Airport to Pennsylvania up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Pennsylvania?

    The cheapest time of day to fly to Pennsylvania is generally in the evening, when round-trip flights cost $191 on average. Morning departures are around 20% more expensive than evening flights, on average. The most expensive time of day to fly to Pennsylvania is generally at night, which is peak travel time and where the average cost of a ticket is $264.

Top tips for finding cheap flights to Pennsylvania

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Newark $67 one-way - $62 round-trip; Philadelphia $166 one-way - $241 round-trip

Reviews of the top airlines flying from Midway to Pennsylvania

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Pennsylvania. 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 Pennsylvania? 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 4249 reviews
7.0Food
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
Airline reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Not clean and was told I would get a great seat and it was not great at all

Good- no snacks on a 4+ hour flight is painful but more painful was the lack of WiFi.

Flight got delayed for 5 hours no good explanation was offered ;(

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

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

Information on your arrival and departure airports