Cheap flights from Phoenix Sky Harbor Intl Airport to Chicago from $108

The month of September is, on average, the cheapest month to fly to Chicago from Phoenix Sky Harbor Intl Airport, with most prices found around $273. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Phoenix Sky Harbor Intl Airport to Chicago during August average around $289.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $343. 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 Phoenix Sky Harbor Intl Airport to Chicago for around $515.

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Phoenix Sky Harbor Intl Airport to Chicago during this time can be as low as $308. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $422.

Fly from Phoenix Sky Harbor Intl to Chicago O'Hare Intl for the best Phoenix Sky Harbor Intl - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Phoenix Sky Harbor Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $277 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Phoenix Sky Harbor Intl Airport for as low as $232 on momondo.

You could potentially save up to 9% on your flight if you consider stops on a Phoenix Sky Harbor Intl Airport to Chicago flight.

As of May 2026, prices for Phoenix Sky Harbor Intl Airport to Chicago flights are approximately 34% more expensive when compared to flights at the same time last year.

United Airlines and Southwest are the most popular carriers operating from Phoenix Sky Harbor Intl to Chicago

American Airlines, Frontier and United Airlines are the top three most popular airlines that fly to Chicago from Phoenix Sky Harbor Intl Airport according to our data. American Airlines is the first choice among our users, with 37% 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 10% of flights between Phoenix and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 154 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.

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 7% of their flights experiencing any sort of delay.

Chicago (ORD) was the most common stop: 25% of momondo users choosing 1-stop flights on this route connected there.

Flights via Denver (DEN) offer the lowest average round-trip price of $148.

Flights connecting via Minneapolis (MSP) have the shortest average one-way travel time: 6h 21m.

Chicago (ORD) has the shortest average layover time for this route: 1h 34m.

The number of flights available between Phoenix Sky Harbor Intl Airport and Chicago is 57 per day as of May 2026. The most frequent departure time is 7:00AM, with 48% of daily flights leaving at noon.

The number of flights available between Phoenix Sky Harbor Intl Airport and Chicago is 400 per week as of May 2026. The most frequent departure day is Mon, with 17% of weekly flights leaving on this day.