Flying from Chicago to Cancun can be expensive. Our search helps you compare cheap flights, airfare deals, and flight tickets across airlines and agencies so you can book at the best price.
We scan trusted travel agencies and airline booking systems for the route Chicago - Cancun (CHI - CUN). We do not sell tickets or add fees - you choose where to buy.
Airfares vary by date, time, and airport. Use filters to find the best option by departure/arrival time, number of stops, airline or alliance, and booking channel.
If your dates are flexible, check the low-fare calendar to find the cheapest days. Booking round-trip in one order often reduces fees, and prices usually rise as departure approaches.
We also recommend you to look through the prices for return tickets from Cancun to Chicago.
Airfares found by our users in the past 24 hours
The price for these dates could change. Use search to get the best price.
Average round-trip airfares from Chicago to Cancun by months
| Month | Round-Trip |
|---|---|
| January 2026 | find now |
| February 2026 | 08.02 - 12.02from C$260 |
| March 2026 | 28.03 - 31.03from C$395 |
| April 2026 | 12.04 - 25.04from C$344 |
| May 2026 | 22.05 - 26.05from C$275 |
| June 2026 | find now |
| July 2026 | 30.07 - 04.08from C$362 |
| August 2026 | 04.08 - 09.08from C$389 |
| September 2026 | find now |
| October 2026 | find now |
| November 2026 | 29.11 - 06.12from C$464 |
| December 2026 | find now |
Prices shown are based on searches from the last few days. Ticket prices can change and depend on availability at the time of booking.
Airlines are flying from Chicago to Cancun
| Southwest Airlines | Frontier Airlines |
Popular flights from Chicago
Frequently asked questions about flights from Chicago to Cancun
How long does the flight from Chicago to Cancun take?
Flight duration from Chicago to Cancun varies by route, airline, and number of stops. Direct flights are faster; connecting flights may take longer. Use our search to compare options and see exact durations for your dates.
Are there direct flights from Chicago to Cancun?
Availability of direct flights from Chicago to Cancun depends on the route and season. Use our search and filter by "Direct" or "Non-stop" to see only direct options. We compare offers from many airlines and agencies.
Which airlines fly from Chicago to Cancun?
Several airlines may operate flights from Chicago to Cancun. On this page you can see airlines that serve this route. Our search compares prices across airlines and agencies so you can choose the best offer. We do not sell tickets; you book directly with the airline or agency.
What is the cheapest month to fly from Chicago to Cancun?
Prices from Chicago to Cancun vary by month and demand. On this page you can see average round-trip prices by month. Use the low-fare calendar and monthly table to find the cheapest dates. Booking in advance and avoiding peak seasons often helps get the best price.