MDW → CUNChicago to Cancún

live

Direct flights from Chicago (MDW) to Cancún (CUN): 10 nonstop departures observed each week across 1 airline. 88% of the last 8 tracked flights arrived within 15 minutes of schedule. The median arrival is on schedule. No cancellations were recorded across the 9 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 2 November 2026 at 21:13 UTC.

Today, MDW → CUN

Mon 2 Nov · local times
  1. 08:55 WN218Southwest Airlines Left 08:47 Landed 13:10 −30

Checked MDW board 14:54 · CUN board 16:13

MDW Chicago smooth · +8
CUN Cancún smooth · +0
2,309 km · ~3h 28m est.
dep bank 08:00–09:0510x weekly
Runs reliable · 1 airline · 10x weekly · nonstop
88% on time

of the last 8 tracked MDW → CUN flights arrived within 15 minutes

Median arrival delay is −1 min. 0 of 9 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →

Median arrival−1 minacross the last 8 arrivals
Flight time~3h 28mestimated from route distance
Weekly departures10x1 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 AirlinesWN88% on time

Flights WN228 08:00 Sa · WN218 08:55 Mo Su · WN216 09:05 daily

History

operated legs · board outcomes
11-02WN218dep −8 → arr−30
11-01WN218dep +21 → arr−5
10-31WN216dep +21 → arr−1
10-31WN228dep +32 → arr+10
10-30WN216dep +5 → arr+1
10-29WN216dep −4 → arr−19
10-28WN216departed+28
10-27WN216dep +25 → arr+34
10-26WN216dep +4 → arr−14

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 +8 min smooth ⛅ overcast · S 9 kt Full MDW delay board →
CUNCancún +0 min smooth 🌤 mostly cloudy · NNE 4 kt Full CUN delay board →

Weather lens

Conditions are tightest at MDW: a 34% chance of a 15+ minute delay. In this weather, the more delayed of the two airports is typically about +9 min. Both figures come from the two airports' delay records in similar weather. 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 77/100. 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 10 flights a week (daily). Since one carrier owns the route, a single disruption tends to ripple through the day.