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Find cheap flights from Chicago Midway Airport to Pennsylvania from $41

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 6/21. 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
0 bags
Wed 7/10
Wed 7/17

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Best Pennsylvania Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Philadelphia
Philadelphianonstop$48
Pittsburgh
Pittsburgh1 stop$110
Harrisburg
Harrisburg1 stop$252
Allentown
Allentown1 stop$348
New York
New York1 stop$96

Good to know

Low season

February

High season

November

Cheapest flight

$41
Best time to beat the crowds but there is an average 18% increase in price.
Most popular time to fly and prices are also 16% lower on average.
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 to Pennsylvania from Chicago Midway Airport 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 to Pennsylvania with an airline and back to Chicago Midway Airport 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 to Pennsylvania from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

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: Philadelphia $39 one-way - $78 round-trip
  • Morning departure is around 8% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 3 airlines serving 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
DeltaOverall score based on 10295 reviews
8.0Entertainment
8.6Crew
8.2Boarding
7.9Comfort
7.4Food
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

The plane was not on time for boarding or departure or arrivals.

Because our flight from marsh Harbor to Fort Lauderdale was over three hours delayed it caused us to miss our flight in Fort Lauderdale. Because we missed that flight, it cost us nearly $100 apiece for four different travelers which totaled nearly $400. We are seeking a reimbursement for the flight that we missed in Fort Lauderdale Florida.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

The whole day was a nightmare. Flight extremely late. Boarding was a mess of a nightmare.

Never been on this flight as i had missed it due to delayed connecting flight

Missed our departing flight due to poor baggage drop staff. At the airport with 2 & 1/2 hours to spare and waited in bag check in until 15 minutes prior to gates closing before baggage staff asked us to move to the front of the line. We weren’t the only passengers that missed the flight. Poor organizational operations by Spirit staff. Otherwise , the return trip was fine.

The flight attendants were very personable, extremely friendly, and had a very good feeling of the energy around them not to mention they’re very funny and engaging. What made up for the discomfort of the seats and the fact that the plane sat for a long time on the Turmac. Not sure if the pilot was new, but the landing was very rough sort of like I was at a magic mountain theme park ride that was built in 1959

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

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

Book cheap flights from Chicago to Pennsylvania

Recent round-trip flight deals

7/30Tue
nonstopFrontier
2h 03mMDW-PHL
8/4Sun
nonstopFrontier
2h 17mPHL-MDW
$70
7/3Wed
nonstopFrontier
2h 01mMDW-PHL
7/10Wed
nonstopFrontier
2h 08mPHL-MDW
$73
10/23Wed
1 stopDelta
5h 17mMDW-EWR
11/20Wed
1 stopDelta
5h 03mEWR-MDW
$156
9/4Wed
1 stopDelta
5h 10mMDW-EWR
9/11Wed
1 stopDelta
5h 04mEWR-MDW
$167
7/10Wed
1 stopSouthwest
10h 30mMDW-DCA
7/11Thu
1 stopSouthwest
10h 05mDCA-MDW
$200
7/9Tue
nonstopSouthwest
2h 05mMDW-LGA
7/10Wed
nonstopSouthwest
2h 25mLGA-MDW
$228
7/1Mon
1 stopAllegiant Air
11h 57mMDW-EWR
7/4Thu
1 stopAllegiant Air
27h 29mEWR-MDW
$294
7/29Mon
2 stops
27h 04mMDW-EWR
8/2Fri
1 stop
9h 45mEWR-MDW
$317
7/1Mon
1 stopAllegiant Air
11h 57mMDW-EWR
7/7Sun
1 stopAllegiant Air
27h 29mEWR-MDW
$323
7/29Mon
3 stops
25h 40mMDW-EWR
8/2Fri
1 stop
9h 45mEWR-MDW
$326

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Recent one-way flight deals

6/21Fri
nonstopFrontier
2h 01mMDW-PHL
$41
6/29Sat
nonstopFrontier
2h 01mMDW-PHL
$44
8/7Wed
1 stopDelta
5h 06mMDW-EWR
$78
7/9Tue
1 stopDelta
7h 40mMDW-PHL
$88
7/12Fri
1 stopAllegiant Air
10h 58mMDW-EWR
$106
6/21Fri
1 stopAllegiant Air
19h 51mMDW-EWR
$107
6/17Mon
2 stops
17h 46mMDW-PHL
$146
9/16Mon
2 stops
16h 26mMDW-PIT
$148
7/3Wed
1 stopPorter Airlines
5h 20mMDW-EWR
$234
6/26Wed
1 stopPorter Airlines
6h 30mMDW-EWR
$244

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Last minute flights from Midway to Pennsylvania

Last minute flight, train and bus deals

6/12Wed
nonstopFrontier
2h 01mMDW-PHL
6/18Tue
nonstopFrontier
2h 12mPHL-MDW
$88
6/15Sat
nonstopFrontier
2h 01mMDW-PHL
6/18Tue
nonstopFrontier
2h 12mPHL-MDW
$95
6/13Thu
multi-stopDelta
6h 00mMDW-PHL
6/16Sun
multi-stopDelta
3h 48mPHL-MDW
$245
6/14Fri
multi-stopDelta
7h 52mMDW-PHL
6/16Sun
multi-stopDelta
3h 48mPHL-MDW
$270
6/14Fri
multi-stopAllegiant Air
10h 57mMDW-EWR
6/21Fri
multi-stopAllegiant Air
10h 23mEWR-MDW
$313
6/14Fri
multi-stopAllegiant Air
10h 57mMDW-EWR
6/21Fri
multi-stopAllegiant Air
10h 23mEWR-MDW
$320
6/12Wed
nonstopSouthwest
1h 55mMDW-PHL
6/13Thu
nonstopSouthwest
2h 05mPHL-MDW
$333
6/12Wed
multi-stopSouthwest
4h 50mMDW-PHL
6/13Thu
nonstopSouthwest
2h 05mPHL-MDW
$342
6/14Fri
multi-stop
10h 57mMDW-EWR
6/17Mon
multi-stop
15h 03mEWR-MDW
$392
6/14Fri
multi-stop
14h 05mMDW-EWR
6/21Fri
multi-stop
10h 23mEWR-MDW
$405

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Chicago Midway Airport - Pennsylvania Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Pennsylvania - Chicago Midway Airport

Cabin classes:

$47