Cheap flights from Arizona to Chicago from $110

The month of April is, on average, the cheapest month to fly to Chicago Midway Airport from Arizona, with most prices found around $268. If you are unable to visit Chicago Midway Airport during the month of April, then departing from Arizona during the month May is also very affordable. Most momondo users find prices during this month for around $321.

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Arizona. The lowest ticket price found for a Friday 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 Arizona 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 Arizona in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $329 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $428. 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 Arizona - Chicago Midway flight prices

You are more likely to see cheaper flights to Chicago Midway Airport from Arizona when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $388 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 Arizona for as low as $292 on momondo.

There is only 1 cabin class available to choose from on Arizona 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.

As of October 2026, there are 1 flights per day flying from Arizona to Chicago Midway Airport. The most common time of day flights depart is 12:00AM, with 34% of flights taking off at noon.

11 flights are operational weekly from Arizona to Chicago Midway Airport as of October 2026. The most popular departure day for this route is Wed, with 82% of flights per week taking off on this day.