Cheap flights from Chicago to Pittsburgh from $59

In general, September is the cheapest month to fly from Chicago to Pittsburgh. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $67. The month of December is another great option to travel to Pittsburgh, with average flight prices from Chicago averaging around $73.

The cheapest day to depart on your flight to Pittsburgh is on a Thursday when prices can be found for as low as $271. This is often the case because there is less demand to fly during this day of the week. Flights from Chicago to Pittsburgh on a Monday will generally be more expensive and average around $443. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

Our data shows that the cheapest Chicago to Pittsburgh flights are usually those with departure times in the afternoon. Our users have found flights to Pittsburgh in the afternoon for as low as $323. Flights to Pittsburgh are more costly in the morning, with an average ticket price of $352. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

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

You are more likely to see cheaper flights to Pittsburgh from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Pittsburgh for around $341 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Pittsburgh from Chicago for as low as $118 on momondo.

No. A direct flight is the cheapest option for a flight between Chicago to Pittsburgh.

As of May 2026, prices for Chicago to Pittsburgh flights are approximately 49% more expensive when compared to flights at the same time last year.

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

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Pittsburgh from Chicago 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 Pittsburgh. Keep in mind that there are 3 different airlines that fly to Pittsburgh on a routine basis, so you have a few additional options to choose from.

Historically, on average around 15% of flights between Chicago and Pittsburgh have experienced a delay on any given week. The average delay length over the past 12 months has been 103 minutes.

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

Wednesday 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, Southwest have had the least number of delays on this route over the last 12 months; with about 15% of their flights experiencing any sort of delay.

The number of flights available between Chicago and Pittsburgh is 49 per day as of May 2026. The most frequent departure time is 9:00PM, with 46% of daily flights leaving in the afternoon.

As of May 2026, there are 343 flights per week flying from Chicago to Pittsburgh. The most common day of the week flights depart is Fri, with 17% of flights taking off on this day.