Cheap flights from Cancún to Chicago from $144

The month of February is, on average, the cheapest month to fly to Chicago from Cancún, with most prices found around $226. If you’re not able to fly to Chicago in February, then January is your next best option. Flight prices from Cancún to Chicago during January average around $227.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $222. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Cancún to Chicago for around $445.

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Cancún to Chicago during this time can be as low as $227. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $343.

Fly from Cancun to Chicago O'Hare Intl for the best Cancun - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Cancún when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $267 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Cancún for as low as $124 on momondo.

There are 4 cabin classes available to choose from on Cancun to Chicago 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 Cancún to Chicago.

As of February 2026, prices for Cancún to Chicago flights are approximately 40% more expensive when compared to flights at the same time last year.

United Airlines and Southwest are the most popular carriers operating from Cancun to Chicago

United Airlines, Frontier and Spirit Airlines are the top three most popular airlines that fly to Chicago from Cancún according to our data. United Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 14% 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 157 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.

As of February 2026, there are 6 flights per day flying from Cancún to Chicago. The most common time of day flights depart is 3:00PM, with 83% of flights taking off in the afternoon.

As of February 2026, there are 44 flights per week flying from Cancún to Chicago. The most common day of the week flights depart is Tue, with 25% of flights taking off on this day.