$57 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 3/31. 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$181
Pittsburgh
Pittsburgh1 stop$182
Harrisburg
Harrisburg1 stop$289
Allentown
Allentown1 stop$294
Erie
Erie2 stops$386
Washington, D.C.
Baltimore1 stop$140
New York
Newark1 stop$103
Philadelphia
Philadelphia1 stop$181
Pittsburgh
Pittsburgh1 stop$182
Harrisburg
Harrisburg1 stop$289
Allentown
Allentown1 stop$294
Erie
Erie2 stops$386
Washington, D.C.
Baltimore1 stop$140
New York
Newark1 stop$103

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, Apr 14 - Tue, Apr 21
Frontier Logo
2:15 pm - 1:16 am
MDW
-
EWR
10h 01m
1 stop
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
$103Frontier
Thu, Apr 16 - Sun, Apr 19
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
$104Frontier
Thu, Apr 16 - Fri, Apr 24
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
$105Frontier
Tue, Apr 14 - Wed, Apr 15
Southwest Logo
5:15 am - 8:15 am
MDW
-
LGA
2h 00mnonstop
Southwest Logo
7:25 am - 8:50 am
LGA
-
MDW
2h 25mnonstop
$159Southwest
Wed, Apr 22 - Wed, Apr 29
Southwest Logo
7:25 pm - 10:30 pm
MDW
-
LGA
2h 05mnonstop
Southwest Logo
10:55 am - 12:20 pm
LGA
-
MDW
2h 25mnonstop
$161Southwest
Fri, Apr 17 - Tue, Apr 21
Delta Logo
6:38 pm - 11:03 pm
MDW
-
MDT
3h 25m
1 stop
Delta Logo
6:00 am - 8:47 am
MDT
-
MDW
3h 47m
1 stop
$289Delta
Sat, May 9 - Sun, May 10
Delta Logo
6:23 am - 12:19 pm
MDW
-
ABE
4h 56m
1 stop
Delta Logo
6:27 am - 1:19 pm
ABE
-
MDW
7h 52m
2 stops
$294Delta
Thu, Apr 16 - Sun, Apr 19
Multiple Airlines Logo
2:15 pm - 12:11 pm
MDW
-
ABE
20h 56m
2 stops
Multiple Airlines Logo
7:53 pm - 8:04 am
ABE
-
MDW
13h 11m
1 stop
$360Multiple Airlines
Thu, Apr 30 - Wed, May 6
Multiple Airlines Logo
7:30 am - 10:51 pm
MDW
-
ABE
14h 21m
2 stops
Multiple Airlines Logo
10:00 am - 8:26 am
ABE
-
MDW
23h 26m
1 stop
$365Multiple Airlines
Thu, Apr 30 - Wed, May 6
Allegiant Air Logo
9:16 am - 9:44 am
MDW
-
ABE
23h 28m
1 stop
Allegiant Air Logo
10:00 am - 8:26 am
ABE
-
MDW
23h 26m
1 stop
$387Allegiant Air
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.

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 Pittsburgh, at $134 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 $177.

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 $202 on average. Morning departures are around 11% 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 $262.

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 $360, 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 February and July, when the average cost of round-trip tickets is $461 and $387 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 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.

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 3 weeks before departure, which saves you about 24% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$57
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly with an average 28% increase in price.
Flight from Chicago Midway Airport to Newark Liberty Airport

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. $174 one-way - $279 round-trip; New York $169 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.
8.0
SouthwestOverall score based on 4333 reviews
7.0Food
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
Airline reviews

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

10.0 ExcellentGwen, Mar 2026
DAL - BNA
Read more Southwest reviews

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I liked it better when you were truer to your roots Am paying more for less fun

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

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.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

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 crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

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!

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

Information on your arrival and departure airports