Cheap flights from Philadelphia to Chicago from $105

The month of November is, on average, the cheapest month to fly to Chicago Midway Airport from Philadelphia, with most prices found around $237. If you are unable to visit Chicago Midway Airport during the month of November, then departing from Philadelphia during the month January is also very affordable. Most momondo users find prices during this month for around $248.

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Philadelphia. The lowest ticket price found for a Friday departure recently was $348. 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 Philadelphia because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $463.

Flying to Chicago Midway Airport from Philadelphia at noon is the least expensive time of day to depart. momondo users have found prices as low as $345 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $397. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Chicago Midway Airport from Philadelphia when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $337 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Philadelphia for as low as $268 on momondo.

There is only 1 cabin class available to choose from on Philadelphia to Chicago Midway Airport 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 21% on your flight if you consider stops on a Philadelphia to Chicago Midway Airport flight.

As of August 2026, prices for Philadelphia to Chicago Midway Airport flights are approximately 147% more expensive when compared to flights at the same time last year.

Southwest is the most popular carrier operating from Philadelphia to Chicago Midway

Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Philadelphia according to our data. Southwest is the first choice among our users, with 67% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 4 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

Historically, on average around 21% of flights between Philadelphia and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 119 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.

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 20% of their flights experiencing any sort of delay.

As of August 2026, 3 flights take off from Philadelphia and land in Chicago Midway Airport each day. The most common flight departure time for this route is 8:00AM, with 44% of daily flights taking off in the afternoon.

As of August 2026, 25 flights take off from Philadelphia and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.