Cheap flights from Chicago to Pennsylvania from $99

The month of October is, on average, the cheapest month to fly to Pennsylvania from Chicago, with most prices found around $264. If you don’t want to visit Pennsylvania in October, then you should wait until January to fly from Chicago, when ticket prices are also cheap, with an average price of $268.

The cheapest day to depart on your flight to Pennsylvania is on a Friday when prices can be found for as low as $288. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $446. These prices are subject to change though, so be sure to set up a Price Alert for flights to Pennsylvania.

Our most recent data shows that the best time of day to fly to Pennsylvania is in the evening. Flights from Chicago to Pennsylvania during this time can be as low as $267. In contrast, the most expensive time of day to depart to Pennsylvania is in the afternoon when prices are around $431.

Fly from Chicago Midway to Pittsburgh for the best Chicago - Pennsylvania flight prices

You are more likely to see cheaper flights to Pennsylvania from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Pennsylvania for around $322 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Pennsylvania from Chicago for as low as $238 on momondo.

There are 4 cabin classes available to choose from on Chicago to Pennsylvania flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Southwest, United Airlines, and Delta are the most popular carriers operating from Chicago to Pennsylvania

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Pennsylvania from Chicago according to our data. United Airlines is the first choice among our users, with 49% of people opting to fly with this airline when traveling to Pennsylvania. Keep in mind that there are 4 different airlines that fly to Pennsylvania on a routine basis, so you have a few additional options to choose from.

As of September 2026, there are 66 flights per day flying from Chicago to Pennsylvania. The most common time of day flights depart is 5:00PM, with 47% of flights taking off in the afternoon.

464 flights are operational weekly from Chicago to Pennsylvania as of September 2026. The most popular departure day for this route is Wed, with 31% of flights per week taking off on this day.