Cheap flights from Phoenix Sky Harbor Intl Airport to Chicago from $140

The month of April is, on average, the cheapest month to fly to Chicago Midway Airport from Phoenix Sky Harbor Intl Airport, with most prices found around $216. If you are unable to visit Chicago Midway Airport during the month of April, then departing from Phoenix Sky Harbor Intl Airport during the month May is also very affordable. Most momondo users find prices during this month for around $312.

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Phoenix Sky Harbor Intl Airport. The lowest ticket price found for a Thursday departure recently was $365. 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 Phoenix Sky Harbor Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $474.

Flying to Chicago Midway Airport from Phoenix Sky Harbor Intl Airport in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $322 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $417. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Phoenix Sky Harbor Intl to Chicago Midway for the best Phoenix Sky Harbor Intl - Chicago Midway flight prices

You are more likely to see cheaper flights to Chicago Midway Airport from Phoenix Sky Harbor Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $375 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 Phoenix Sky Harbor Intl Airport for as low as $292 on momondo.

There is only 1 cabin class available to choose from on Phoenix Sky Harbor Intl Airport 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 17% on your flight if you consider stops on a Phoenix Sky Harbor Intl Airport to Chicago Midway Airport flight.

As of September 2026, prices for Phoenix Sky Harbor Intl Airport to Chicago Midway Airport flights are approximately 202% more expensive when compared to flights at the same time last year.

As of September 2026, there are 1 flights per day flying from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport. The most common time of day flights depart is 12:00AM, with 45% of flights taking off at noon.

The number of flights available between Phoenix Sky Harbor Intl Airport and Chicago Midway Airport is 12 per week as of September 2026. The most frequent departure day is Mon, with 83% of weekly flights leaving on this day.