Cheap flights from Chicago Midway Airport to Mexico from $102

If you’re not able to fly to Mexico in September, then February is your next best option. Flight prices from Chicago Midway Airport to Mexico during February average around $402.

The cheapest day to depart on your flight to Mexico is on a Monday when prices can be found for as low as $389. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $500. These prices are subject to change though, so be sure to set up a Price Alert for flights to Mexico.

Our data shows that the cheapest Chicago Midway Airport to Mexico flights are usually those with departure times in the afternoon. Our users have found flights to Mexico in the afternoon for as low as $431. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $693 on average. Flights to Mexico from Chicago Midway Airport at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

Fly from Chicago Midway to Guadalajara Miguel Hidal for the best Chicago Midway - Mexico flight prices

You are more likely to see cheaper flights to Mexico from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Mexico for around $510 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Mexico from Chicago Midway Airport for as low as $431 on momondo.

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

Volaris, Southwest, and Frontier are the most popular carriers operating from Chicago Midway to Mexico

Southwest, Volaris and Delta are the top three most popular airlines that fly to Mexico from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 63% of people opting to fly with this airline when traveling to Mexico. Keep in mind that there are 6 different airlines that fly to Mexico on a routine basis, so you have a few additional options to choose from.

Historically, on average around 16% of flights between Chicago and Mexico have experienced a delay on any given week. The average delay length over the past 12 months has been 147 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.

Friday 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 13% of their flights experiencing any sort of delay.

The number of flights available between Chicago Midway Airport and Mexico is 5 per day as of February 2026. The most frequent departure time is 6:00PM, with 46% of daily flights leaving in the evening.

As of February 2026, there are 36 flights per week flying from Chicago Midway Airport to Mexico. The most common day of the week flights depart is Thu, with 19% of flights taking off on this day.