$59 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 4/17. 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$144
Pittsburgh
Pittsburgh1 stop$213
Harrisburg
Harrisburg1 stop$229
Allentown
Allentown1 stop$229
Washington, D.C.
Baltimore1 stop$119
New York
Newarknonstop$102
Philadelphia
Philadelphia1 stop$144
Pittsburgh
Pittsburgh1 stop$213
Harrisburg
Harrisburg1 stop$229
Allentown
Allentown1 stop$229
Washington, D.C.
Baltimore1 stop$119
New York
Newarknonstop$102

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

Sun, Mar 8 - Sun, Mar 15
Frontier Logo
7:30 am - 10:30 am
MDW
-
EWR
2h 00mnonstop
Frontier Logo
11:30 am - 1:02 pm
EWR
-
MDW
2h 32mnonstop
$102Frontier
Wed, Apr 22 - Sat, Apr 25
Multiple Airlines Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
Multiple Airlines Logo
5:10 am - 4:13 pm
EWR
-
MDW
12h 03m
1 stop
$103Multiple Airlines
Sat, Apr 18 - Mon, Apr 20
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
Fri, Apr 17 - 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
$106Frontier
Fri, Mar 6 - Sun, Mar 8
Frontier Logo
2:41 pm - 9:30 pm
MDW
-
EWR
5h 49m
1 stop
Frontier Logo
11:30 am - 1:02 pm
EWR
-
MDW
2h 32mnonstop
$107Frontier
Mon, Mar 9 - Thu, Mar 12
Multiple Airlines Logo
2:41 pm - 11:29 pm
MDW
-
EWR
7h 48m
1 stop
Multiple Airlines Logo
11:30 am - 1:02 pm
EWR
-
MDW
2h 32mnonstop
$111Multiple Airlines
Fri, Apr 17 - Sun, Apr 19
Southwest Logo
5:25 am - 8:25 am
MDW
-
LGA
2h 00mnonstop
Southwest Logo
6:00 am - 7:25 am
LGA
-
MDW
2h 25mnonstop
$137Southwest
Wed, Apr 1 - Sun, Apr 5
Southwest Logo
5:10 am - 8:10 am
MDW
-
LGA
2h 00mnonstop
Southwest Logo
9:25 pm - 10:55 pm
LGA
-
MDW
2h 30mnonstop
$142Southwest
Thu, Mar 5 - Sun, Mar 8
Delta Logo
6:00 am - 12:05 pm
MDW
-
ABE
5h 05m
1 stop
Delta Logo
6:32 am - 12:02 pm
ABE
-
MDW
6h 30m
1 stop
$229Delta
Fri, Mar 6 - Mon, Mar 9
Delta Logo
6:20 pm - 11:00 pm
MDW
-
MDT
3h 40m
1 stop
Delta Logo
6:32 pm - 10:31 pm
MDT
-
MDW
4h 59m
1 stop
$229Delta
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 Philadelphia, at $197 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Pittsburgh (PIT), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $217.

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 $322, 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 $432 and $337 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 2 weeks before departure, which saves you about 37% 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$59
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 43% 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.

  • 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 $189 on average. Morning departures are around 25% 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 $261.

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. $144 one-way - $269 round-trip; New York $108 one-way - $227 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 4282 reviews
7.0Food
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
Airline reviews

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

10.0 ExcellentCarol, Feb 2026
DEN - MSP
Read more Southwest reviews

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Paid for premium extra leg room but the bin space for rows 1-3 had to go in rows 4-6 and 4-6 had to go to 7-9 because flight attendants have snacks and their luggage upfront. So we pay extra to have to fight thru traffic to get our bags. Only 2nd day of new seating so hope they fix this.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

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.

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.

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

Information on your arrival and departure airports