$69 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 7/22. 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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Cheap Flights from Midway to Pennsylvania

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Philadelphia
Philadelphia1 stop$235
Pittsburgh
Pittsburgh1 stop$201
Harrisburg
Harrisburg1 stop$289
Allentown
Allentown1 stop$289
Washington, D.C.
Washington, D.C.2 stops$236
New York
New Yorknonstop$184
Philadelphia
Philadelphia1 stop$235
Pittsburgh
Pittsburgh1 stop$201
Harrisburg
Harrisburg1 stop$289
Allentown
Allentown1 stop$289
Washington, D.C.
Washington, D.C.2 stops$236
New York
New Yorknonstop$184

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

Wed, Sep 9 - Fri, Sep 11
Southwest Logo
5:10 am - 8:10 am
MDW
-
LGA
2h 00mnonstop
Southwest Logo
6:00 am - 7:15 am
LGA
-
MDW
2h 15mnonstop
$184Southwest
Sat, Aug 8 - Tue, Aug 11
Southwest Logo
3:10 pm - 6:15 pm
MDW
-
LGA
2h 05mnonstop
Southwest Logo
6:00 am - 7:15 am
LGA
-
MDW
2h 15mnonstop
$187Southwest
Sat, Jul 25 - Sat, Aug 1
Southwest Logo
6:40 pm - 9:50 pm
MDW
-
LGA
2h 10mnonstop
Southwest Logo
5:35 pm - 7:25 pm
LGA
-
MDW
2h 50mnonstop
$189Southwest
Tue, Aug 11 - Wed, Aug 19
Delta Logo
5:10 pm - 12:10 am
MDW
-
EWR
6h 00m
1 stop
Delta Logo
7:05 am - 11:51 am
EWR
-
MDW
5h 46m
1 stop
$191Delta
Wed, Sep 9 - Mon, Sep 14
Southwest Logo
2:40 pm - 5:45 pm
MDW
-
LGA
2h 05mnonstop
Southwest Logo
6:00 am - 7:15 am
LGA
-
MDW
2h 15mnonstop
$192Southwest
Sat, Jul 18 - Tue, Jul 21
Southwest Logo
7:45 am - 10:55 am
MDW
-
LGA
2h 10mnonstop
Southwest Logo
1:35 pm - 3:00 pm
LGA
-
MDW
2h 25mnonstop
$194Southwest
Thu, Aug 6 - Mon, Aug 10
Delta Logo
6:42 pm - 12:04 am
MDW
-
PIT
4h 22m
1 stop
Delta Logo
6:19 pm - 10:36 pm
PIT
-
MDW
5h 17m
1 stop
$201Delta
Sat, Sep 5 - Tue, Sep 8
Frontier Logo
11:45 am - 8:28 pm
MDW
-
PHL
7h 43m
1 stop
Frontier Logo
4:45 pm - 10:47 pm
PHL
-
MDW
7h 02m
1 stop
$235Frontier
Tue, Sep 8 - Mon, Sep 14
Frontier Logo
11:50 am - 10:33 pm
MDW
-
PHL
9h 43m
1 stop
Frontier Logo
6:00 am - 12:07 pm
PHL
-
MDW
7h 07m
1 stop
$240Frontier
Sun, Jul 26 - Sun, Aug 2
Multiple Airlines Logo
9:08 am - 9:41 am
MDW
-
ABE
23h 33m
1 stop
Multiple Airlines Logo
8:00 am - 10:03 pm
ABE
-
MDW
39h 03m
2 stops
$474Multiple Airlines
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 September.

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 5 days was to Pittsburgh, at $181 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 5 days was $247.

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

The average price for all round-trip flights from Chicago Midway Airport to Pennsylvania depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Pennsylvania is generally in the evening, when round-trip flights cost $273 on average. Morning departures are around 2% more expensive than evening flights, on average. The most expensive time of day to fly to Pennsylvania is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $288.

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 $350, 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 November, when tickets cost $67 (return) on average. On the other hand, the most expensive months are February and June, when the average cost of round-trip tickets is $321 and $166 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, Thursday is the cheapest day to fly on average and Tuesday is the most expensive. Flying from Pennsylvania back to Chicago Midway Airport, the best deals are generally found on Friday, with Sunday being the most expensive.

Good to know

Low seasonJanuary
Cheapest flight$69
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly with an average 18% increase in price.
Flight from Chicago Midway Airport to Pittsburgh

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.

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: Washington, D.C. $168 one-way - $278 round-trip; New York $165 one-way - $273 round-trip; Philadelphia $171 one-way - $295 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 4246 reviews
8.6Crew
7.0Food
7.5Entertainment
8.0Comfort
8.1Boarding
Airline reviews

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.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

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.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

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

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent experience. WiFi worked on this leg of My trip

wifi wasn't working correctly so couldn't watch live tv

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 !!!!!!!

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

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

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

Information on your arrival and departure airports