$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 12/3. 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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Flight Deals

Cheap Flights from Midway to Pennsylvania

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Philadelphia
Philadelphia1 stop$110
Pittsburgh
Pittsburgh2 stops$112
Harrisburg
Harrisburg1 stop$229
Allentown
Allentown1 stop$229
Erie
Erie2 stops$598
Washington, D.C.
Baltimorenonstop$96
New York
New York1 stop$110
Philadelphia
Philadelphia1 stop$110
Pittsburgh
Pittsburgh2 stops$112
Harrisburg
Harrisburg1 stop$229
Allentown
Allentown1 stop$229
Erie
Erie2 stops$598
Washington, D.C.
Baltimorenonstop$96
New York
New York1 stop$110

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, Nov 13 - Sat, Nov 15
Frontier Logo
10:12 am - 9:22 pmMDW-PHL
10h 10m1 stop
Frontier Logo
6:19 am - 11:30 amPHL-MDW
30h 11m1 stop
$110Frontier
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Wed, Nov 12 - Wed, Nov 19
Frontier Logo
2:06 pm - 11:27 pmMDW-LGA
8h 21m1 stop
Frontier Logo
6:24 am - 12:41 pmLGA-MDW
7h 17m1 stop
$110Frontier
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Wed, Nov 12 - Wed, Nov 19
Frontier Logo
2:06 pm - 12:33 amMDW-JFK
9h 27m1 stop
Frontier Logo
6:20 am - 12:41 pmJFK-MDW
7h 21m1 stop
$110Frontier
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Thu, Dec 4 - Mon, Dec 8
Southwest Logo
2:30 pm - 9:55 pmMDW-PIT
6h 25m2 stops
Southwest Logo
6:45 pm - 7:15 pmPIT-MDW
1h 30mnonstop
$112Southwest
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Thu, Dec 4 - Mon, Dec 8
Southwest Logo
8:10 am - 4:45 pmMDW-PIT
7h 35m1 stop
Southwest Logo
5:30 am - 12:35 pmPIT-MDW
8h 05m2 stops
$122Southwest
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Fri, Dec 12 - Mon, Dec 15
Multiple Airlines Logo
8:42 pm - 8:31 pmMDW-EWR
22h 49m1 stop
Multiple Airlines Logo
10:30 pm - 8:46 amEWR-MDW
11h 16m1 stop
$131Multiple Airlines
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Fri, Dec 12 - Sun, Dec 14
Multiple Airlines Logo
8:42 pm - 6:59 pmMDW-EWR
21h 17m2 stops
Multiple Airlines Logo
11:30 am - 1:01 pmEWR-MDW
2h 31mnonstop
$137Multiple Airlines
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Tue, Jan 20 - Wed, Jan 21
Delta Logo
6:35 pm - 11:15 pmMDW-EWR
3h 40m1 stop
Delta Logo
9:47 am - 12:48 pmEWR-MDW
4h 01m1 stop
$177Delta
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Sat, Jan 17 - Sun, Jan 18
Delta Logo
5:00 pm - 11:46 pmMDW-PIT
5h 46m1 stop
Delta Logo
6:00 am - 10:34 amPIT-MDW
5h 34m1 stop
$177Delta
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Fri, Nov 14 - Sun, Nov 16
Allegiant Air Logo
5:35 pm - 10:41 amMDW-ABE
16h 06m2 stops
Allegiant Air Logo
4:22 pm - 12:02 pmABE-MDW
20h 40m2 stops
$382Allegiant Air
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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 Philadelphia, at $90 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 $90.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $218 on average.

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 October, when tickets cost $179 (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, Monday 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.

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 42% 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 and prices are also 6% lower on average.
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 $205 on average. Morning departures are around 8% 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 $229.

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. $158 one-way - $263 round-trip; Newark $68 one-way - $98 round-trip; Philadelphia $88 one-way - $129 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
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
8.1Boarding
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

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.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

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

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