Cheap flights from Chicago to Philadelphia from $99

The cheapest month to fly to Philadelphia from Chicago is in January. Flight prices, which tend to average around $227, are often lower during this time because this is during the off-season. The month of October is another great option to travel to Philadelphia, with average flight prices from Chicago averaging around $262.

The cheapest day to depart from Chicago to Philadelphia is on a Friday. Travelers who choose to depart for Philadelphia on a Friday will often find tickets for as low as $293. On the other hand, Monday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $441.

According to our data, the cheapest time of day to fly to Philadelphia is in the evening. momondo users have found flights departing from Chicago to Philadelphia in the evening for as low as $271. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Philadelphia is in the afternoon when prices are around $423.

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

You are more likely to see cheaper flights to Philadelphia from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Philadelphia for around $327 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Philadelphia from Chicago for as low as $238 on momondo.

There are 4 cabin classes available to choose from on Chicago to Philadelphia 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 Philadelphia.

As of October 2026, prices for Chicago to Philadelphia flights are approximately 97% 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 Philadelphia

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Philadelphia from Chicago according to our data. United Airlines is the first choice among our users, with 56% of people opting to fly with this airline when traveling to Philadelphia. Keep in mind that there are 6 different airlines that fly to Philadelphia on a routine basis, so you have a few additional options to choose from.

Historically, on average around 21% of flights between Chicago and Philadelphia have experienced a delay on any given week. The average delay length over the past 12 months has been 143 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. Monday 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 21% of their flights experiencing any sort of delay.

The number of flights available between Chicago and Philadelphia is 23 per day as of October 2026. The most frequent departure time is 4:00PM, with 44% of daily flights leaving in the afternoon.

As of October 2026, there are 167 flights per week flying from Chicago to Philadelphia. The most common day of the week flights depart is Fri, with 31% of flights taking off on this day.