Cheap flights from North America to Chicago from $59

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from North America, with most prices found around $283. If you are unable to visit Chicago Midway Airport during the month of January, then departing from North America during the month February is also very affordable. Most momondo users find prices during this month for around $308.

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from North America. The lowest ticket price found for a Thursday departure recently was $324. 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, Monday is the most expensive day to depart from North America because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $402.

Flying to Chicago Midway Airport from North America in the evening is the least expensive time of day to depart. momondo users have found prices as low as $302 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $387. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Dallas/Fort Worth to Chicago Midway for the best North America - Chicago Midway flight prices

There are 3 cabin classes available to choose from on North America 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.

No. A direct flight is the cheapest option for a flight between North America to Chicago Midway Airport.

Southwest, Delta, and Frontier are the most popular carriers operating from North America to Chicago Midway

Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from North America according to our data. Southwest is the first choice among our users, with 67% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 6 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

Historically, on average around 21% of flights between North America and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 120 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.

Wednesday 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, Southwest 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.

As of November 2026, there are 47 flights per day flying from North America to Chicago Midway Airport. The most common time of day flights depart is 8:00AM, with 45% of flights taking off at noon.

As of November 2026, there are 332 flights per week flying from North America to Chicago Midway Airport. The most common day of the week flights depart is Mon, with 24% of flights taking off on this day.