Cheap flights from Pittsburgh to Chicago from $59

The month of October is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Pittsburgh averaging around $279.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $408. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Pittsburgh because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $584.

Flying to Chicago O'Hare Intl Airport from Pittsburgh in the evening is the least expensive time of day to depart. momondo users have found prices as low as $396 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $626. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Pittsburgh to Chicago O'Hare Intl for the best Pittsburgh - Chicago O'Hare Intl flight prices

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Pittsburgh when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $322 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Pittsburgh for as low as $91 on momondo.

Historically, on average around 9% 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 142 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.

Thursday 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 May 2026, there are 54 flights per day flying from Pittsburgh to Chicago O'Hare Intl Airport. The most common time of day flights depart is 7:00PM, with 48% of flights taking off at noon.

The number of flights available between Pittsburgh and Chicago O'Hare Intl Airport is 380 per week as of May 2026. The most frequent departure day is Mon, with 16% of weekly flights leaving on this day.