Cheap flights from Chicago to Pittsburgh from $48

In general, August 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 $171. The month of September is another great option to travel to Pittsburgh, with average flight prices from Chicago averaging around $206.

The cheapest day to depart on your flight to Pittsburgh is on a Thursday when prices can be found for as low as $253. 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 Sunday will generally be more expensive and average around $399. 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 evening. Our users have found flights to Pittsburgh in the evening for as low as $285. Flights to Pittsburgh are more costly at noon, with an average ticket price of $317. Departure times at noon 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 $316 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 $166 on momondo.

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

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

As of February 2026, prices for Chicago to Pittsburgh flights are approximately 26% more expensive when compared to flights at the same time last year.

Southwest, Delta, and United Airlines 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 106 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.

Tuesday 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 14% of their flights experiencing any sort of delay.

The number of flights available between Chicago and Pittsburgh is 35 per day as of February 2026. The most frequent departure time is 5:00PM, with 41% of daily flights leaving in the evening.

As of February 2026, there are 249 flights per week flying from Chicago to Pittsburgh. The most common day of the week flights depart is Thu, with 20% of flights taking off on this day.