Which airline is most reliable for DTW (Detroit) to MDW (Chicago)?

The most reliable airline on the DTW to MDW route is Southwest Airlines, with an on-time arrival rate of 81%.

How often are flights delayed from DTW to MDW?

About 20% of flights from DTW to MDW experience delays. 80% arrive on time.

What's the average delay on DTW to MDW flights?

When flights from DTW to MDW are delayed, the average delay is approximately 60 minutes.

Is a short connection safe after a DTW to MDW flight?

With 80% of DTW to MDW flights arriving on time and an average delay of 60 minutes when late, a connection under 60 minutes at MDW is risky. We recommend at least 75-90 minutes for domestic connections after this route.

DTW → MDW

DTW (Detroit) to MDW (Chicago)

DTW (Detroit) to MDW (Chicago) flights arrive on time 80% of the time. The most reliable airline on this route is Southwest Airlines at 81%. The average delay is 60 minutes. Delays on this route are most often caused by the airline (crew, maintenance, or boarding).

Source: Bureau of Transportation Statistics. Updated August 2026.

DTW → MDW on-time performance by month

JanFebMarAprMayJunJulAugSepOctNovDec

Worse

Better

This route is on time most of the time. About 80% of flights arrive on schedule.

Delays on this route are most often caused by the airline (crew, maintenance, or boarding).

Accurate?

Airlines are roughly equal on this route — Southwest Airlines leads slightly at 81% vs SkyWest Airlines at 80%.

Airline Comparison

Southwest Airlines leads at 81% on time; SkyWest Airlines trails at 80%.

Accurate?

Good to know

Departing from DTW

80% on time

Expect ~18 min sitting on the taxiway after your gate pushes back. DTW has long runway queues.

TSA is currently ~5 min. Best time: 4 AM (about 5 min).

More about DTW →

Arriving at MDW

80% on time

When flights into MDW are late, the average delay is 58 minutes. Build buffer if you have ground plans.

If connecting at MDW: TSA is ~5 min right now. Allow at least 60 minutes for a domestic connection.

More about MDW →Connection times at MDW →

Flight cancelled or delayed?

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DTW Airport MDW Airport

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Data last updated August 2026. Source: Bureau of Transportation Statistics.