July is the cheapest month to fly this route, with average fares around $292 round trip.
Average round-trip fares by departure month, based on current availability.
| Month | Avg Price | Lowest | Relative Cost | |
|---|---|---|---|---|
| May 2026 | $359 | $301 | ||
| June 2026 | $339 | $256 | ||
| July 2026 | $292 | $256 | Best | |
| August 2026 | $360 | $313 | Peak |
Departing on Tuesday offers the lowest average fares at $304. Friday departures are the most expensive at $338, a difference of $34.
The best time to fly is July. Set up an alert and we'll notify you when prices drop.
Get Started Free →The cheapest month to fly from Chicago to Cancun is July, with average round-trip fares around $292. The lowest fare found in July is $256.
Tuesday departures are the cheapest, averaging $304 round trip. The most expensive day is Friday at $338.
Based on current pricing trends, booking for July travel offers the best value. Avoid August if possible, as fares average $360 compared to $292 in the cheapest month. May is a solid middle-ground option at $359.
Flying in July instead of August can save you approximately $68 per round trip. The cheapest month averages $292 while the most expensive averages $360.
Airlines, flight times, price calendar, and more for Chicago to Cancun
View ORD → CUN Details