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Find cheap flights from Chicago Midway Airport to Pennsylvania from $49

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 6/29. 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
Fri 6/7
Fri 6/14

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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$78
Pittsburgh
Pittsburgh1 stop$100
Harrisburg
Harrisburg1 stop$313
New York
New York1 stop$99

Good to know

Low season

February

High season

November

Cheapest flight

$49
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 5% increase in price.
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 $47 one-way - $82 round-trip
  • Morning departure is around 23% 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 10810 reviews
8.6Crew
8.2Boarding
8.0Entertainment
7.9Comfort
7.4Food
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

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

Flight was delayed 2+ hours missed a concert because of it…

Everything was fine. I really enjoyed our early flight from philly to Orlando as well as the crew.

The flight experience was terrible. Extra bag charges were exorbitant, and the customer service was incredibly poor. Flight attendants were rude and unhelpful. Post-flight, we endured a one-hour wait for our luggage, only to find our bags severely damaged. Overall, a highly disappointing experience with Spirit Airlines. Not recommended.

Seats could use more padding. Kind of hard on the tush.

The plane hit a bird and had to turn around. Very reasonable and I am thankful that occurred. However, the way they cancelled the flight after telling us just another 30min was not ok. They then used our plane for another flight.

Amazed that Spirit can even get planes in the air, would never use again.

The flight was really great I was surprised with Spirit.

Spirit canceled the flight 20 hours before it was scheduled to take off. They didn’t send a clear message and had no alternative flight for a week. What a terrible airline! Never use them.

It was my wife traveling so she ends up not traveling because they didn’t help her at the counter they blame it to the check in system at the airport and they told her if you want to travel in the other flight you have to pay $99 dollars and she will have to go to Las Vegas and then to Los Angeles almost 12 hours flight or to travel another day and we asked for a refund they said no refund and we called customer service and they didn’t help know she will travel the end of this week.

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

Book cheap flights from Chicago to Pennsylvania

Recent round-trip flight deals

5/30Thu
nonstopFrontier
2h 01mMDW-PHL
6/5Wed
nonstopFrontier
2h 11mPHL-MDW
$78
6/14Fri
nonstopFrontier
2h 01mMDW-PHL
6/16Sun
nonstopFrontier
2h 14mPHL-MDW
$79
6/7Fri
nonstopFrontier
2h 01mMDW-PHL
6/10Mon
nonstopFrontier
2h 11mPHL-MDW
$80
5/17Fri
nonstopFrontier
2h 00mMDW-PHL
5/21Tue
nonstopFrontier
2h 21mPHL-MDW
$81
5/30Thu
1 stopDelta
5h 03mMDW-PIT
6/3Mon
1 stopDelta
4h 01mPIT-MDW
$156
5/14Tue
1 stopDelta
7h 12mMDW-PHL
5/15Wed
1 stopDelta
5h 06mPHL-MDW
$175
6/18Tue
1 stopSouthwest
8h 20mMDW-PHL
6/19Wed
2 stopsSouthwest
7h 50mPHL-MDW
$261
5/14Tue
nonstopSouthwest
1h 50mMDW-PHL
5/15Wed
nonstopSouthwest
2h 10mPHL-MDW
$267
5/30Thu
3 stops
15h 59mMDW-PIT
6/3Mon
2 stops
15h 13mPIT-MDW
$465
5/30Thu
3 stops
15h 59mMDW-PIT
6/3Mon
3 stops
20h 00mPIT-MDW
$609

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Recent one-way flight deals

6/29Sat
nonstopFrontier
2h 01mMDW-PHL
$49
7/20Sat
nonstopFrontier
1h 59mMDW-PHL
$50
5/26Sun
1 stopDelta
4h 20mMDW-PIT
$78
7/15Mon
1 stopDelta
5h 51mMDW-PHL
$88
5/13Mon
nonstopSouthwest
1h 50mMDW-PHL
$154
7/15Mon
2 stops
19h 03mMDW-PHL
$173
5/31Fri
2 stopsAllegiant Air
18h 22mMDW-MDT
$179
5/13Mon
1 stopSouthwest
4h 40mMDW-PHL
$180
5/27Mon
1 stopAllegiant Air
9h 25mMDW-PIT
$189
5/27Mon
2 stops
15h 25mMDW-PIT
$201

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Last minute flights from Midway to Pennsylvania

Last minute flight, train and bus deals

5/9Thu
nonstopFrontier
1h 56mMDW-PHL
5/14Tue
nonstopFrontier
2h 17mPHL-MDW
$102
5/10Fri
nonstopFrontier
2h 03mMDW-PHL
5/21Tue
nonstopFrontier
2h 21mPHL-MDW
$105
5/11Sat
nonstopFrontier
2h 01mMDW-PHL
5/21Tue
nonstopFrontier
2h 21mPHL-MDW
$111
5/10Fri
nonstopFrontier
2h 03mMDW-PHL
5/22Wed
nonstopFrontier
2h 13mPHL-MDW
$119
5/9Thu
nonstopFrontier
1h 56mMDW-PHL
5/16Thu
nonstopFrontier
2h 16mPHL-MDW
$121
5/13Mon
nonstopFrontier
2h 03mMDW-PHL
5/15Wed
nonstopFrontier
2h 17mPHL-MDW
$122
5/10Fri
multi-stopDelta
4h 17mMDW-PHL
5/15Wed
multi-stopDelta
5h 06mPHL-MDW
$239
5/13Mon
multi-stopDelta
5h 05mMDW-PHL
5/15Wed
multi-stopDelta
5h 06mPHL-MDW
$288
5/10Fri
multi-stopDelta
4h 17mMDW-PHL
5/11Sat
multi-stopDelta
6h 02mPHL-MDW
$300
5/11Sat
multi-stop
26h 01mMDW-PIT
5/18Sat
multi-stop
28h 27mPIT-MDW
$1,019

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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:

$50