Cheap flights from Chicago Midway Airport to Cancún from $166

If you don’t want to visit Cancún in October, then you should wait until February to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $356.

The cheapest day to depart from Chicago Midway Airport to Cancún is on a Sunday when prices can be found for as low as $452. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $520. These prices are subject to change though, so be sure to set up a Price Alert for flights to Cancún.

Our most recent data shows that the best time of day to fly to Cancún is in the morning. Flights from Chicago Midway Airport to Cancún during this time can be as low as $490. Flights to Cancún are more costly at noon, with an average ticket price of $664. Departure times at noon fall within the peak daily travel times, which is why tickets can be more expensive.

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

You are more likely to see cheaper flights to Cancún from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Cancún for around $504 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Cancún from Chicago Midway Airport for as low as $443 on momondo.

There are 2 cabin classes available to choose from on Chicago Midway Airport to Cancún flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Delta is the most popular carrier operating from Chicago Midway to Cancun

Southwest, Frontier and Aeromexico are the top three most popular airlines that fly to Cancún from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 72% of people opting to fly with this airline when traveling to Cancún. Keep in mind that there are 4 different airlines that fly to Cancún on a routine basis, so you have a few additional options to choose from.

Historically, on average around 25% of flights between Chicago and Cancún have experienced a delay on any given week. The average delay length over the past 12 months has been 125 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

Tuesday 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 24% of their flights experiencing any sort of delay.

Atlanta (ATL) was the most common stop: 75% of momondo users choosing 1-stop flights on this route connected there.

Flights via Guadalajara (GDL) offer the lowest average round-trip price of $345.

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 5h 30m.

Atlanta (ATL) has the shortest average layover time for this route: 1h 51m.

1 flights are operational daily from Chicago Midway Airport to Cancún as of July 2026. The most popular departure time for this route is 6:00AM, with 100% of flights per day taking off at noon.

As of July 2026, 8 flights take off from Chicago Midway Airport and land in Cancún each week. The most common flight departure day for this route is Mon, with 25% of weekly flights taking off on this day.