Cheap flights from Cancún to Chicago from $142

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Cancún. The lowest ticket price found for a Thursday departure recently was $358. 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, Tuesday is the most expensive day to depart from Cancún because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $552.

Flying to Chicago Midway Airport from Cancún at noon is the least expensive time of day to depart. momondo users have found prices as low as $358 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $538. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Cancun to Chicago Midway for the best Cancun - Chicago Midway flight prices

There is only 1 cabin class available to choose from on Cancun to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Historically, on average around 11% of flights between Cancún 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. Saturday 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 11% of their flights experiencing any sort of delay.

The number of flights available between Cancún and Chicago Midway Airport is 1 per day as of February 2026. The most frequent departure time is 3:00PM, with 100% of daily flights leaving in the afternoon.

As of February 2026, 7 flights take off from Cancún and land in Chicago Midway Airport each week. The most common flight departure day for this route is Sat, with 29% of weekly flights taking off on this day.