Cheap flights from Philadelphia to Chicago from $100

The month of January is, on average, the cheapest month to fly to Chicago from Philadelphia, with most prices found around $230. If you’re not able to fly to Chicago in January, then November is your next best option. Flight prices from Philadelphia to Chicago during November average around $237.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $354. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Philadelphia to Chicago for around $499.

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Philadelphia to Chicago during this time can be as low as $344. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $414.

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

You are more likely to see cheaper flights to Chicago from Philadelphia when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $309 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Philadelphia for as low as $274 on momondo.

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

As of August 2026, prices for Philadelphia to Chicago flights are approximately 90% more expensive when compared to flights at the same time last year.

Frontier, United Airlines, and Southwest are the most popular carriers operating from Philadelphia to Chicago

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Chicago from Philadelphia according to our data. United Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 18% 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 141 minutes.

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Saturday 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.

Detroit (DTW) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Flights via Atlanta (ATL) offer the lowest average round-trip price of $143.

Flights connecting via Detroit (DTW) have the shortest average one-way travel time: 3h 50m.

Atlanta (ATL) has the shortest average layover time for this route: 1h 07m.

As of August 2026, 33 flights take off from Philadelphia and land in Chicago each day. The most common flight departure time for this route is 5:00PM, with 41% of daily flights taking off at noon.

As of August 2026, 237 flights take off from Philadelphia and land in Chicago each week. The most common flight departure day for this route is Mon, with 23% of weekly flights taking off on this day.