Cheap flights from Philadelphia to Chicago from $100

The month of November is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Philadelphia averaging around $260.

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 $351. 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 Philadelphia because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $524.

Flying to Chicago O'Hare Intl Airport from Philadelphia in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $342 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $445. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Philadelphia when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $306 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 Philadelphia for as low as $267 on momondo.

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

Delta and United Airlines are the most popular carriers operating from Philadelphia to Chicago O'Hare Intl

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Philadelphia according to our data. United Airlines is the first choice among our users, with 51% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 5 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

Historically, on average around 14% 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 159 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, United Airlines have had the least number of delays on this route over the last 12 months; with about 9% of their flights experiencing any sort of delay.

As of August 2026, 34 flights take off from Philadelphia and land in Chicago O'Hare Intl Airport each day. The most common flight departure time for this route is 5:00PM, with 42% of daily flights taking off at noon.

As of August 2026, there are 242 flights per week flying from Philadelphia to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Sun, with 21% of flights taking off on this day.