$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 6/3. 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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Cheap Flights from Midway to Pennsylvania

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Philadelphia
Philadelphia1 stop$190
Pittsburgh
Pittsburghnonstop$177
Harrisburg
Harrisburg1 stop$289
Allentown
Allentown1 stop$289
Washington, D.C.
Baltimorenonstop$197
New York
New Yorknonstop$177
Philadelphia
Philadelphia1 stop$190
Pittsburgh
Pittsburghnonstop$177
Harrisburg
Harrisburg1 stop$289
Allentown
Allentown1 stop$289
Washington, D.C.
Baltimorenonstop$197
New York
New Yorknonstop$177

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, Jun 23 - Wed, Jul 8
Southwest Logo
7:45 pm - 10:55 pm
MDW
-
LGA
2h 10mnonstop
Southwest Logo
7:25 am - 8:50 am
LGA
-
MDW
2h 25mnonstop
$177Southwest
Thu, Jun 4 - Mon, Jun 8
Southwest Logo
6:50 pm - 9:15 pm
MDW
-
PIT
1h 25mnonstop
Southwest Logo
8:10 pm - 8:40 pm
PIT
-
MDW
1h 30mnonstop
$177Southwest
Tue, Jun 2 - Wed, Jun 3
Southwest Logo
4:40 pm - 9:20 pm
MDW
-
PIT
3h 40m
1 stop
Southwest Logo
6:40 am - 3:50 pm
PIT
-
MDW
10h 10m
2 stops
$178Southwest
Wed, Jun 3 - Wed, Jun 10
Frontier Logo
6:00 am - 8:56 pm
MDW
-
LGA
13h 56m
1 stop
Frontier Logo
6:25 am - 10:11 pm
LGA
-
MDW
16h 46m
1 stop
$180Frontier
Sat, Oct 17 - Wed, Oct 21
Delta Logo
10:35 am - 6:37 pm
MDW
-
PIT
7h 02m
1 stop
Delta Logo
6:05 pm - 9:45 pm
PIT
-
MDW
4h 40m
1 stop
$182Delta
Thu, Jul 2 - Sun, Jul 5
Southwest Logo
7:45 pm - 10:55 pm
MDW
-
LGA
2h 10mnonstop
Southwest Logo
6:00 am - 7:20 am
LGA
-
MDW
2h 20mnonstop
$182Southwest
Sat, Aug 22 - Wed, Aug 26
Frontier Logo
6:00 am - 7:57 pm
MDW
-
LGA
12h 57m
1 stop
Frontier Logo
10:00 pm - 10:11 pm
LGA
-
MDW
25h 11m
1 stop
$185Frontier
Wed, Jun 3 - Tue, Jun 9
Frontier Logo
12:04 pm - 7:10 pm
MDW
-
PHL
6h 06m
1 stop
Frontier Logo
4:35 pm - 10:11 pm
PHL
-
MDW
6h 36m
1 stop
$190Frontier
Sat, Jun 27 - Wed, Jul 8
Delta Logo
9:54 am - 4:55 pm
MDW
-
EWR
6h 01m
1 stop
Delta Logo
6:00 am - 9:08 am
EWR
-
MDW
4h 08m
1 stop
$197Delta
Thu, Jul 9 - Mon, Jul 13
Delta Logo
5:10 pm - 12:50 am
MDW
-
PIT
6h 40m
1 stop
Delta Logo
5:30 am - 10:05 am
PIT
-
MDW
5h 35m
1 stop
$197Delta
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.

How much is a round-trip flight from Chicago Midway Airport to Pennsylvania?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Pennsylvania departing in June.

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 $209 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 $247.

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 $212 on average. Morning departures are around 15% 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 $276.

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 $350, 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 November, when tickets cost $67 (return) on average. On the other hand, the most expensive months are February and April, when the average cost of round-trip tickets is $321 and $170 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, Thursday 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.

Good to know

Low seasonJanuary
Cheapest flight$59
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly with an average 23% increase in price.
Flight from Chicago Midway Airport to Pittsburgh

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. $144 one-way - $280 round-trip; New York $145 one-way - $246 round-trip; Philadelphia $163 one-way - $325 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 4295 reviews
7.5Entertainment
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
Airline reviews

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

2.0 MediocreAnonymous, May 2026
MCO - MDW
Read more Southwest reviews

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

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

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

Information on your arrival and departure airports