Cheap flights from Chicago to Mexico from $111

If you’re not able to fly to Mexico in January, then February is your next best option. Flight prices from Chicago to Mexico during February average around $384.

The cheapest day to depart on your flight to Mexico is on a Monday when prices can be found for as low as $399. 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 $424. 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 to Mexico flights are usually those with departure times in the evening. Our users have found flights to Mexico in the evening for as low as $395. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are $441 on average. Flights to Mexico from Chicago in the afternoon 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 - Mexico flight prices

You are more likely to see cheaper flights to Mexico from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Mexico for around $394 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Mexico from Chicago for as low as $363 on momondo.

There are 4 cabin classes available to choose from on Chicago to Mexico flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Viva, JetBlue, and Air Canada are the most popular carriers operating from Chicago to Mexico

Volaris, Viva and United Airlines are the top three most popular airlines that fly to Mexico from Chicago according to our data. Volaris is the first choice among our users, with 38% of people opting to fly with this airline when traveling to Mexico. Keep in mind that there are 10 different airlines that fly to Mexico on a routine basis, so you have a few additional options to choose from.

Historically, on average around 21% 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 159 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights at night 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, Aeromexico have had the least number of delays on this route over the last 12 months; with about 9% of their flights experiencing any sort of delay.

As of September 2026, there are 23 flights per day flying from Chicago to Mexico. The most common time of day flights depart is 1:00AM, with 37% of flights taking off at noon.

As of September 2026, there are 164 flights per week flying from Chicago to Mexico. The most common day of the week flights depart is Fri, with 16% of flights taking off on this day.