$89 Find Cheap Flights from Chicago to Pennsylvania - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Pennsylvania departing on 8/22. 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.
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Cheap Flights from Chicago to Pennsylvania

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Philadelphia
Philadelphianonstop$177
Pittsburgh
Pittsburgh1 stop$147
Harrisburg
Harrisburgnonstop$279
Allentown
Allentown1 stop$255
State College
State Collegenonstop$279
Washington, D.C.
Baltimorenonstop$177
New York
Newark1 stop$198
Philadelphia
Philadelphianonstop$177
Pittsburgh
Pittsburgh1 stop$147
Harrisburg
Harrisburgnonstop$279
Allentown
Allentown1 stop$255
State College
State Collegenonstop$279
Washington, D.C.
Baltimorenonstop$177
New York
Newark1 stop$198

Book Cheap Chicago 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 Chicago 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 Chicago to Pennsylvania

Thu, Oct 15 - Sun, Oct 18
Frontier Logo
7:29 pm - 10:47 pm
ORD
-
PHL
2h 18mnonstop
Frontier Logo
4:47 pm - 6:24 pm
PHL
-
ORD
2h 37mnonstop
$176Frontier
Thu, Aug 20 - Mon, Aug 24
Frontier Logo
6:00 am - 9:17 am
ORD
-
PHL
2h 17mnonstop
Frontier Logo
2:45 pm - 7:59 pm
PHL
-
ORD
6h 14m
1 stop
$177Frontier
Fri, Oct 16 - Sun, Oct 18
Multiple Airlines Logo
9:38 am - 5:59 pm
ORD
-
PHL
7h 21m
1 stop
Multiple Airlines Logo
4:47 pm - 6:24 pm
PHL
-
ORD
2h 37mnonstop
$184Multiple Airlines
Sat, Oct 10 - Sun, Oct 11
Multiple Airlines Logo
9:38 am - 5:59 pm
ORD
-
PHL
7h 21m
1 stop
Multiple Airlines Logo
4:47 pm - 6:24 pm
PHL
-
ORD
2h 37mnonstop
$184Multiple Airlines
Fri, Sep 11 - Thu, Sep 17
United Airlines Logo
12:55 pm - 4:01 pm
ORD
-
IAD
2h 06mnonstop
United Airlines Logo
6:13 am - 7:28 am
IAD
-
ORD
2h 15mnonstop
$192United Airlines
Thu, Sep 3 - Sun, Sep 6
United Airlines Logo
6:25 am - 9:23 am
ORD
-
IAD
1h 58mnonstop
United Airlines Logo
10:27 pm - 11:40 pm
IAD
-
ORD
2h 13mnonstop
$192United Airlines
Wed, Oct 21 - Sat, Oct 24
Delta Logo
1:55 pm - 6:37 pm
ORD
-
DCA
3h 42m
1 stop
Delta Logo
8:00 am - 12:13 pm
DCA
-
ORD
5h 13m
1 stop
$197Delta
Wed, Sep 9 - Wed, Sep 16
Delta Logo
7:00 am - 12:34 pm
ORD
-
DCA
4h 34m
1 stop
Delta Logo
9:40 am - 12:59 pm
DCA
-
ORD
4h 19m
1 stop
$197Delta
Tue, Sep 1 - Tue, Sep 1
American Airlines Logo
10:09 am - 1:30 pm
ORD
-
EWR
2h 21mnonstop
American Airlines Logo
5:19 pm - 7:20 pm
EWR
-
ORD
3h 01mnonstop
$201American Airlines
Tue, Sep 1 - Tue, Sep 1
American Airlines Logo
3:05 pm - 6:23 pm
ORD
-
LGA
2h 18mnonstop
American Airlines Logo
8:29 pm - 10:30 pm
LGA
-
ORD
3h 01mnonstop
$201American Airlines
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?

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 to Pennsylvania departing in August.

Flight prices are below average for this route right now.

Flights to Pennsylvania from Chicago usually cost between $186 and $325 in August.
The lowest price found in the past 5 days was $177 on Frontier (Aug 20-Aug 24).

What is the cheapest Chicago 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 found in the last 5 days was to Philadelphia, at $126 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 $126.

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

The average price for all round-trip flights from Chicago 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 at night, when round-trip flights cost $264 on average. Morning departures are around 20% 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 $410.

Can I save money by flying with a layover from Chicago 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 2 stops layover the cheapest option at $320 on average.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago 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 to Pennsylvania is October, when tickets cost $223 (return) on average. On the other hand, the most expensive months are March and June, when the average cost of round-trip tickets is $384 and $384 respectively.

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

The average price of all round-trip flights from Chicago to Pennsylvania clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Pennsylvania on a Friday, 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 calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago 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 to Pennsylvania, you should book around 3 weeks before departure, which saves you about 31% 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

$89
Most popular time to fly with an average 8% increase in price.
Flight from Chicago O'Hare Airport to Reagan Washington National Airport

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

 
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 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.
8.0
SouthwestOverall score based on 4229 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
Airline reviews

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

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

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.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

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

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

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!!

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

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.

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

Cabin class types available on flights to Pennsylvania

Cabin classes available on flights to Pennsylvania. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.