Cheap flights from Pittsburgh to Chicago from $69

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Pittsburgh, with most prices found around $201. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Pittsburgh during the month October is also very affordable. Most momondo users find prices during this month for around $248.

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Pittsburgh. The lowest ticket price found for a Tuesday departure recently was $363. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. 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 $421.

Flying to Chicago Midway Airport from Pittsburgh at noon is the least expensive time of day to depart. momondo users have found prices as low as $343 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $391. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

There is only 1 cabin class available to choose from on Pittsburgh to Chicago Midway 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 74% on your flight if you consider stops on a Pittsburgh to Chicago Midway Airport flight.

Historically, on average around 13% 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 107 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.

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 13% of their flights experiencing any sort of delay.

As of March 2026, 2 flights take off from Pittsburgh and land in Chicago Midway Airport each day. The most common flight departure time for this route is 8:00AM, with 36% of daily flights taking off at noon.

As of March 2026, 14 flights take off from Pittsburgh and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 21% of weekly flights taking off on this day.