MDW → CUNChicago to Cancún

live

Direct flights from Chicago (MDW) to Cancún (CUN): 7 nonstop departures observed each week across 1 airline. The median arrival is 9 minutes late. No cancellations were recorded across the 4 tracked flights. The nonstop covers 2,309 km, an estimated 3 hours 28 minutes in the air. Measured by Pro Flight Search from live flight boards at Chicago and Cancún. Updated 17 October 2026 at 04:55 UTC.

Today, MDW → CUN

Sat 17 Oct · local times
  1. · WN216Southwest Airlines On schedule CUN 13:05scheduled
  2. · WN228Southwest Airlines On schedule CUN 11:45scheduled

Checked MDW board 23:55 · CUN board 23:39

MDW Chicago heavy · +45
CUN Cancún smooth · +0
2,309 km · ~3h 28m est.
dep bank 08:00–09:057x weekly
Running clean · 1 airline · 7x weekly · nonstop
70 / 100

route health from live MDW and CUN delay boards

Median arrival delay is +9 min. 0 of 4 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →

Median arrival+9 minacross the last 4 operated legs
Flight time~3h 28mestimated from route distance
Weekly departures7x1 direct airline on the leg

The week

scheduled departures · origin local time
06121824
Mon
Tue
Wed
Thu
Fri
Sat
Sun
Southwest Airlines

Each mark is a scheduled departure at its origin-local time, observed operating in the last 7 days. Today is highlighted.

Who flies it

observed on the boards · 7 days
Southwest AirlinesWN

Flights WN228 08:00 Sa · WN216 09:05 daily

History

operated legs · board outcomes
10-16WN216dep +0 → arr−4
10-15WN216dep +12 → arr+9
10-14WN216dep +26 → arr+15
10-13WN216arrived−15

Actual board outcomes rather than schedules, paired departure and arrival per flight and day.

Full board history, day by day →

Airports right now

live boards
MDWChicago +45 min heavy 🌤 scattered clouds · NNW 12 kt Full MDW delay board →
CUNCancún +0 min smooth 🌤 mostly cloudy · N 0 kt Full CUN delay board →

Weather lens

Current conditions put the pressure at MDW: 35% odds of a 15+ minute delay and around +9 min expected when it bites, measured from this route's own weather-matched delay history. See live delays → · Weather risk by airport →

How the Chicago to Cancún route actually runs

Pro Flight Search records official board updates for nonstop MDW to CUN flights through the day: schedules, estimates, gate pushes and actual departures. The verdict above comes from operated flights, so it reflects what this route does rather than what the timetable promises.

Planning around a delay? Live airport delays · Weather delay risk map · Will a delayed flight be cancelled? · Do planes make up time in the air? · How we measure

Cite this data

Journalists, bloggers, and researchers may cite this page with attribution and a link to Pro Flight Search.

Suggested citation

Pro Flight Search — Chicago (MDW) to Cancún (CUN) route reliability, measured from operated flights on official airport boards.

Canonical URL
https://proflightsearch.com/search-flights/MDW-CUN
How we measure this →

MDW to CUN questions

Is MDW–CUN running on time right now?

Mostly on schedule. The departure side at MDW is the weaker end, route health score 70/100. The airports section above carries the live status and delay window at both ends.

Morning or evening flight on MDW–CUN?

Operators schedule morning departures around 08:00 from MDW. Earlier flights typically land before destination-airport delays accumulate later in the day; check the CUN delay card to confirm conditions when you'd arrive.

How long is the flight from MDW to CUN?

Great-circle distance is 2,309 km. With typical jet cruise speed plus taxi, climb and descent, expect roughly 193–228 min gate-to-gate on this route.

How often does MDW–CUN fly?

Southwest Airlines runs the route with about 8 flights a week (daily). Since one carrier owns the route, a single disruption tends to ripple through the day.