$93 Find Cheap Flights from Chicago Midway Airport to Pennsylvania - Compare and Save

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Cheap Flights from Midway to Pennsylvania

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Philadelphia
1h 50mNonstop
from $181per person
Pittsburgh
1h 20mNonstop
from $290per person
Harrisburg
3h 29m2 stops
from $366per person
Allentown
5h 04m2 stops
from $369per person
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Booking Insights

Price, demand and travel trends for Chicago Midway Airport to Pennsylvania flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Chicago Midway Airport to Pennsylvania recently?

The cheapest fare from Chicago Midway Airport to Pennsylvania in the last week was $181 round-trip, to Philadelphia (PHL).

How do fares into airports in Pennsylvania compare?

According to KAYAK data from the last 12 months, the cheapest airports to fly into Pennsylvania from Chicago Midway Airport are:

• Philadelphia (PHL) (avg. price $338)
• Pittsburgh (PIT) (avg. price $344)
• Allentown-Bethlehem (ABE) (avg. price $375)

Are flights from Chicago Midway Airport to Pennsylvania cheaper or more expensive than last year?

Fares from Chicago Midway Airport to Pennsylvania are about 25% higher than they were in November last year, averaging $344 round-trip.

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

January is typically the cheapest month to fly from Chicago Midway Airport to Pennsylvania, with round-trip fares averaging $210. June and February are usually the most expensive, averaging $413 and $404, respectively.

How do fares from Chicago Midway Airport to Pennsylvania vary by day of the week?

On average, Wednesday is the cheapest day to fly from Chicago Midway Airport to Pennsylvania and Sunday is the most expensive. Looking at the past 12 months of KAYAK data, it's 40% more expensive to fly on a Sunday compared to Wednesday.

What's the best time of day to fly from Chicago Midway Airport to Pennsylvania?

It's cheapest to fly to Pennsylvania in the evening with average prices of $330. The morning is the most expensive time to fly, with average prices of $346.

What's the best time to book a flight from Chicago Midway Airport to Pennsylvania?

Book your flights 21 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 43% compared to booking at the last minute (within 2 weeks of departure).

Key details for Chicago Midway Airport to Pennsylvania flights

Low season

January

Cheapest flight

$93
Beat the crowds with an average 60% drop in travelers.
The most popular month to fly with an average 35% increase in travelers.
One-way flight from Chicago Midway Airport to Philadelphia

Your Chicago Midway Airport to Pennsylvania flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Chicago Midway Airport to Pennsylvania?

    Yes. Fares from Chicago Midway Airport to Pennsylvania are low right now. As a rule of thumb, a round-trip under $270 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Chicago Midway Airport to Pennsylvania?

    Over the past 12 months, round-trip fares from Chicago Midway Airport to Pennsylvania have typically cost between $270 and $446.

  • What are the main airports serving Pennsylvania?

    There are 25 airports in Pennsylvania. 80% of KAYAK users choose Philadelphia (PHL) as their arrival airport, while 19% choose Pittsburgh (PIT).

  • Which airlines fly nonstop from Chicago Midway Airport to Pennsylvania?

    Based on the flight schedule for the next 3 months, just one airline regularly flies nonstop from Chicago Midway Airport to Pennsylvania: Southwest.

  • Which destinations in Pennsylvania can I fly nonstop from Chicago Midway Airport?

    Based on the flight schedule for the next 3 months, you can fly nonstop from Chicago Midway Airport to 2 destinations in Pennsylvania: Philadelphia and Pittsburgh.

  • Is it cheaper to fly with a layover from Chicago Midway Airport to Pennsylvania?

    Yes, nonstop flights from Chicago Midway Airport to Pennsylvania average $345 over the past 12 months. Flights with a layover can cost less, cheapest when connecting through Orlando (MCO) (avg. price $188) or Atlanta Hartsfield-Jackson (ATL) (avg. price $275).

  • How long is a flight from Chicago Midway Airport to Pennsylvania?

    Nonstop flights from Chicago Midway Airport to Pennsylvania take 1h 44m on average. The fastest scheduled flight takes 1h 20m, flying into Pittsburgh (PIT).

  • Which cabin classes are available from Chicago Midway Airport to Pennsylvania?

    On flights from Chicago Midway Airport to Pennsylvania you can only book Economy Class.

  • What are some popular landmarks around Pennsylvania?

    Pennsylvania is home to many popular sights. KAYAK travelers' favorites include:

    • Philadelphia Convention Center
    • PNC Ballpark
    • Rittenhouse Square
    • Philadelphia Stadium

  • What are the earliest and latest flights from Chicago Midway Airport to Pennsylvania?

    The earliest nonstop flight from Chicago Midway Airport to Pennsylvania departs at 6:20 am and the latest leaves at 9:25 pm. Nonstop flights take about 1h 44m.

Your guide to booking Chicago Midway Airport to Pennsylvania flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 21 weeks before your trip. KAYAK data shows fares in this window are around 43% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • Flexible with your dates? Fly in January to save some money. It's typically the cheapest month on this route, while flights in June will cost you the most.
  • Fly out on a Wednesday to get the cheapest fares. Avoid Sunday flights, which are about 40% more expensive.
  • If you're watching your budget, fly into Philadelphia (PHL) which has the lowest average airfare in the region. Just remember to budget for any onward travel by bus, car or domestic flight.
  • Start your trip in Philadelphia, the most popular destination in Pennsylvania. From there, it's easy to continue on to other popular spots such as Pittsburgh, Lancaster and Erie.
  • Time or money? If speed matters most, fly from Chicago Midway Airport to Pittsburgh (PIT). If you're after the lowest fares, Philadelphia (PHL) is usually your best bet.

Reviews of the top airlines flying from Midway to Pennsylvania

 
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 4219 reviews
7.0Food
8.6Crew
8.0Comfort
7.5Entertainment
8.1Boarding
Airline reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

8.0 ExcellentEmmalee, Oct 2026
Read more Southwest reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

Southwest’s point to point system caused a 2 hour delay due to the crew being late from their inbound flight. Also, the WiFi and entertainment didn’t work on the plane.

A) Checked my luggage at the gate but never got to pre board B) if we are helping with checking our carryon and waiting 40 minutes for it we should have some privileges c) luggage took 40-45 minutes to come.. d) I asked for another snack and was told the plane is full.. seriously a small snack

I like the staff members they were super nice and helpful very sweet people :)

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

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.

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.

More options for your flight from Midway to Pennsylvania

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