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 83%.

How often are flights delayed from DTW to MDW?

About 19% of flights from DTW to MDW experience delays. 81% 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 62 minutes.

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

With 81% of DTW to MDW flights arriving on time and an average delay of 62 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 81% of the time. The most reliable airline on this route is Southwest Airlines at 83%. The average delay is 62 minutes. Delays on this route are most often caused by the airline (crew, maintenance, or boarding).

Source: Bureau of Transportation Statistics. Updated May 2026.

DTW → MDW on-time performance by month

JanFebMarAprMayJunJulAugSepOctNovDec

Worse

Better

This route is on time most of the time. About 81% 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 83% vs SkyWest Airlines at 80%.

Airline Comparison

Southwest Airlines leads at 83% on time; SkyWest Airlines trails at 80%.

Accurate?

Good to know

Departing from DTW

84% on time

Expect ~17 min sitting on the taxiway after your gate pushes back. DTW has long runway queues.

TSA is currently ~11 min. Best time: 4 AM (about 5 min).

More about DTW →

Arriving at MDW

78% on time

When flights into MDW are late, the average delay is 56 minutes. Build buffer if you have ground plans.

If connecting at MDW: TSA is ~25 min right now. Allow at least 60 minutes for a domestic connection.

More about MDW →Connection times at MDW →

Flight cancelled or delayed?

Check what Southwest Airlines owes you — refund rights, action plan, complaint email. Free.

Let us watch your flight

We worry about delays, TSA, weather, and gates so you don't have to.

DTW Airport MDW Airport

Check the return: MDW → DTW

Flying this route?

Enter your flight number for a personalized delay briefing.

Check your flight

Know someone flying soon?

Send them the link — delay data, TSA waits, weather, all free.

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