Cheap flights from Pittsburgh to Chicago from $104

The month of April is, on average, the cheapest month to fly to Chicago from Pittsburgh, with most prices found around $300. If you’re not able to fly to Chicago in April, then February is your next best option. Flight prices from Pittsburgh to Chicago during February average around $324.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $426. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Pittsburgh to Chicago for around $595.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Pittsburgh to Chicago during this time can be as low as $445. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $514.

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

You are more likely to see cheaper flights to Chicago from Pittsburgh when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $357 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Pittsburgh for as low as $181 on momondo.

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

You could potentially save up to 36% on your flight if you consider stops on a Pittsburgh to Chicago flight.

As of October 2026, prices for Pittsburgh to Chicago flights are approximately 45% more expensive when compared to flights at the same time last year.

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

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Pittsburgh according to our data. United Airlines is the first choice among our users, with 52% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 11% of flights between Pittsburgh and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 125 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 7% of their flights experiencing any sort of delay.

As of October 2026, 58 flights take off from Pittsburgh and land in Chicago each day. The most common flight departure time for this route is 4:00PM, with 40% of daily flights taking off in the afternoon.

As of October 2026, 408 flights take off from Pittsburgh and land in Chicago each week. The most common flight departure day for this route is Sun, with 16% of weekly flights taking off on this day.