Nonstop flights from Chicago to Cancún
Southwest Airlines flies this route 1 to 2 times a day.
MDWChicago Midway International
1,434 mi · 12 flights a week
CUNCancún Cancun International
When they leave
Chicago time6:25a9:55aFirst departure 6:25 AM, last 9:55 AM
Two in the morning, 6:25 AM to 9:55 AM.
Every flight
Earliest first
Schedules last checked Sep 19, 2026. Times are local.
Flying from Chicago to Cancún
Southwest Airlines is the only airline flying nonstop from Chicago to Cancún, 1 to 2 times a day on the Boeing 737 MAX 8 and Boeing 737-700.
There are 1 or 2 flights every day of the week. The first arrival in Cancún is at 10:00 AM and the last at 1:30 PM. The flight covers 1,434 miles.
Flying back, Cancún to Chicago has 7 nonstop flights a week. O'Hare (ORD) also has nonstop flights to Cancún, 31 a week.
Return flights
Every Chicago airport
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Find the cheapest day to fly from Chicago to Cancún.
Schedules as of Oct 9, 2026.