$49 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 10/16. 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

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$120
Pittsburgh
Pittsburghnonstop$107
Harrisburg
Harrisburg1 stop$239
Allentown
Allentown1 stop$197
Washington, D.C.
Baltimorenonstop$92
New York
New Yorknonstop$137
Philadelphia
Philadelphia1 stop$120
Pittsburgh
Pittsburghnonstop$107
Harrisburg
Harrisburg1 stop$239
Allentown
Allentown1 stop$197
Washington, D.C.
Baltimorenonstop$92
New York
New Yorknonstop$137

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

Thu, Oct 16 - Mon, Oct 20
Southwest Logo
6:40 pm - 9:00 pmMDW-PIT
1h 20mnonstop
Southwest Logo
5:50 pm - 11:55 pmPIT-MDW
7h 05m1 stop
$107Southwest
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Mon, Oct 27 - Thu, Oct 30
Southwest Logo
9:55 pm - 12:15 amMDW-PIT
1h 20mnonstop
Southwest Logo
5:10 am - 1:05 pmPIT-MDW
8h 55m2 stops
$112Southwest
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Tue, Oct 21 - Sun, Oct 26
Frontier Logo
8:05 am - 4:35 pmMDW-PHL
7h 30m1 stop
Frontier Logo
6:10 am - 7:25 amPHL-MDW
2h 15mnonstop
$120Frontier
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Thu, Oct 30 - Sun, Nov 2
Frontier Logo
10:12 am - 6:30 pmMDW-PHL
7h 18m1 stop
Frontier Logo
5:15 am - 6:30 amPHL-MDW
2h 15mnonstop
$122Frontier
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Mon, Oct 27 - Thu, Oct 30
Southwest Logo
4:35 pm - 11:35 pmMDW-PIT
6h 00m2 stops
Southwest Logo
8:05 pm - 11:15 pmPIT-MDW
4h 10m1 stop
$122Southwest
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Fri, Oct 3 - Sun, Oct 5
Frontier Logo
8:15 am - 11:16 amMDW-PHL
2h 01mnonstop
Frontier Logo
6:00 am - 7:11 amPHL-MDW
2h 11mnonstop
$123Frontier
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Mon, Oct 6 - Thu, Oct 16
Multiple Airlines Logo
5:33 pm - 1:06 amMDW-EWR
6h 33m1 stop
Multiple Airlines Logo
5:15 am - 11:46 pmEWR-MDW
19h 31m1 stop
$165Multiple Airlines
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Wed, Oct 8 - Wed, Oct 15
Multiple Airlines Logo
8:05 am - 10:29 pmMDW-LGA
13h 24m2 stops
Multiple Airlines Logo
6:30 am - 1:38 pmLGA-MDW
8h 08m1 stop
$169Multiple Airlines
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Tue, Oct 7 - Wed, Oct 15
Delta Logo
5:04 pm - 12:59 amMDW-EWR
6h 55m1 stop
Delta Logo
6:00 am - 8:40 amEWR-MDW
3h 40m1 stop
$177Delta
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Thu, Jan 15 - Mon, Jan 19
Delta Logo
9:30 am - 1:24 pmMDW-PIT
2h 54m1 stop
Delta Logo
10:23 am - 12:35 pmPIT-MDW
3h 12m1 stop
$177Delta
Find Deal
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 Pittsburgh, at $77 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 $84.

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 $171, 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 September, when tickets cost $165 (return) on average. On the other hand, the most expensive months are February and March, when the average cost of round-trip tickets is $290 and $287 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, Friday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Pennsylvania back to Chicago Midway Airport, the best deals are generally found on Friday, with Monday 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 33% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$49
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 20% 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.

  • 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 $179 on average. Morning departures are around 21% 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 $222.

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. $112 one-way - $240 round-trip; Philadelphia $89 one-way - $152 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 4242 reviews
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

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

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