$92 Find Cheap Flights from Chicago to Pennsylvania - Compare and Save

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Cheap Flights from Chicago to Pennsylvania

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Philadelphia
Philadelphia1 stop$176
Pittsburgh
Pittsburgh1 stop$279
Harrisburg
Harrisburgnonstop$339
Allentown
Allentownnonstop$339
State College
State Collegenonstop$339
New York
New Yorknonstop$259
Philadelphia
Philadelphia1 stop$176
Pittsburgh
Pittsburgh1 stop$279
Harrisburg
Harrisburgnonstop$339
Allentown
Allentownnonstop$339
State College
State Collegenonstop$339
New York
New Yorknonstop$259
Booking Insights

KAYAK's insights & trends for Chicago to Pennsylvania flights

Get data-powered insights and trends into flights from Chicago 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 to Pennsylvania?

Flight prices are below average for this route right now.

Flights to Pennsylvania from Chicago usually cost between $243 and $382 in December.
The lowest price found in the past 5 days was $176 on Frontier (Dec 16-Jan 6).

What is the cheapest Chicago to Pennsylvania flight route?

The cheapest ticket to Pennsylvania from Chicago found in the last 5 days was to Philadelphia, at $154 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Philadelphia (PHL), and the cheapest round-trip airline ticket found on this route in the last 5 days was $154.

What is the cheapest time of day to fly to Pennsylvania?

The cheapest time of day to fly to Pennsylvania is generally at night, when round-trip flights cost $269 on average. Morning departures are around 18% cheaper than evening flights, on average. The most expensive time of day to fly to Pennsylvania is generally in the evening, which is peak travel time and where the average cost of a ticket is $436.

Can I save money by flying with a layover from Chicago to Pennsylvania?

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $348 on average.

What is the cheapest month to fly from Chicago to Pennsylvania?

The cheapest month for flights from Chicago to Pennsylvania is January, when tickets cost $272 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $390 and $386 respectively.

What’s the cheapest day of the week to fly from Chicago to Pennsylvania?

If your flying dates are flexible, you should consider flying to Pennsylvania on a Thursday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Chicago to Pennsylvania. For your return ticket, we recommend flying on a Friday and avoiding Sundays for the best deals.

How far in advance should I book a flight from Chicago to Pennsylvania?

To get a below average price on the flight from Chicago to Pennsylvania, you should book around 4 weeks before departure, which saves you about 38% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low season

February

Cheapest flight

$92
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Chicago Midway Airport to Philadelphia

Flights from Chicago to Pennsylvania: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from Chicago to Pennsylvania 
EmmaleeFlew with Southwest-Oct 2026
Don't choose an evening return flight because delays throughout the day will compound. The same issue happened the last time I flew to Chicago in 2024, the flight arrived at the destination after 2am.
RogerFlew with Japan Airlines-Jun 2025
Make sure when you go from one airline to another that your bag is marked properly so they can get it on the right damn airplane. I did that and it still didn’t make it.

FAQs - booking Pennsylvania flights

  • How does KAYAK find such low prices on flights from Chicago 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 to Pennsylvania.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Pennsylvania?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago 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 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 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 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 to Pennsylvania up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 4 airlines serving from Chicago to Pennsylvania

 
Need help choosing which airline to fly with from Chicago 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.
7.9
SouthwestOverall score based on 4218 reviews
8.0Comfort
7.0Food
8.1Boarding
8.6Crew
7.4Entertainment
Airline reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

8.0 ExcellentEmmalee, Oct 2026
Read more Southwest reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

Southwest’s point to point system caused a 2 hour delay due to the crew being late from their inbound flight. Also, the WiFi and entertainment didn’t work on the plane.

A) Checked my luggage at the gate but never got to pre board B) if we are helping with checking our carryon and waiting 40 minutes for it we should have some privileges c) luggage took 40-45 minutes to come.. d) I asked for another snack and was told the plane is full.. seriously a small snack

I like the staff members they were super nice and helpful very sweet people :)

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The guy in front of me was talking constantly, even when the pilot was making announcements. I found this very disrespectful to the pilot and to others.

The TVs on the plane were all broken and inoperable. No snacks or food were served. Plane was very old and uncomfortable.

Takeoff delayed 2 hrs. Boarded on time to find we were missing part of the flight crew. Then informed that they had loaded too much fuel. Spent 1 1/2 hrs sitting there burning off the excess, which included a couple of laps around the runway until we were light enough to fly! Ridiculous!

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

The seats are very small, that is all the staff did a good job.

It was great. The staff is always helpful and polite. The app is great and makes the whole trip and process so easy. They even offer a step to step guide to your correct terminal. And they keep all the information you'll need updated. Anything you can think of! Great experience.

Price was crazy watch it if you Chan he your flight

On time, easy boarding. Anytime you sit in an economy seat, it’s uncomfortable. New plane and the bathrooms were in the galley at the back of the plane which seemed odd.

I still prefer Delta, but Delta doesn’t fly to State College PA.

Nothing bad to say about the actual crew or airline. It was nice to have a complimentary FULL can of soda, as well as a snack. Blankets and earbuds were also provided at no cost for this red eye flight. I especially appreciated the free WiFi and movie selection with the Bluetooth option. It helped the flight pass more quickly. No matter who you fly, boarding and disembarking are always SUCH a pain. As I mentioned, this is on the passengers and not the crew!!

Both departure and return flights had mechanical delays. Their planes are antiquated resulting in a two hour flight taking almost four hours to complete.

Crew were helpful, pilot kept us informed about turbulence, snack choice was awesome!

DELAYED AGAIN and AGAIN and AGAIN - not only that, you delay in 20 minute increments for hours and hours instead of having an accurate delay understanding.

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

The flight was delayed till next day ! They kept delaying every 30 minutes then after 3 hours they delayed it till next day. We kept waiting in line standing more than an hour to get the hotel and meal vouchers. There was no communication at all. Everything was bad

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

I appreciate that the flight boarded and departed on time and landed slightly early. However, the plane was completely full (I suspect overbooked) and took a long time to board, during which time the CO2 level in the cabin climbed over 2,200 ppm, which is NOT SAFE given that COVID-19 is still being transmitted at a substantial rate across most of the country and airlines no longer require passengers to mask. Also, the midflight credit card sales pitch was tacky. It's like our airlines are being run by Ferengi.

As it was a very short flight, there was no food only drinks offered. And there was no entertainment. They had to use your own phone for entertainment.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

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.

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

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

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

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

More options for your flight from Chicago to Pennsylvania

Complete your trip to Pennsylvania with a hotel stay or car rental