Cheap flights from Chicago to Cancún from R2 976

If you’re not able to fly to Cancún in January, then February is your next best option. Flight prices from Chicago to Cancún during February average around R6 945.

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

You are more likely to see cheaper flights to Cancún from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Cancún for around R8 163 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Cancún from Chicago for as low as R6 763 on momondo.

There is only 1 cabin class available to choose from on Chicago to Cancún 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 21% 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 155 minutes.

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

Wednesday is statistically the day of the week that experiences the fewest delays on this flight route. Saturday has historically seen more delays on average compared to the rest of the week.

According to our data, Frontier have had the fewest delays on this route over the last 12 months, with about 18% of their flights experiencing any sort of delay.

As of October 2026, 7 flights take off from Chicago and land in Cancún each day. The most common flight departure time for this route is 9:00, with 100% of daily flights taking off at midday.

As of October 2026, 50 flights take off from Chicago and land in Cancún each week. The most common flight departure day for this route is Mon, with 16% of weekly flights taking off on this day.