How often are DTW to MDW flights on time?

Flights from Detroit (DTW) to Chicago (MDW) arrive on time 85% of the time across 12,641 flights of official data.

Which airline is most reliable on the DTW to MDW route?

Southwest Airlines has the best on-time record on this route at 87% across 6,931 flights.

Route reliability

Flights from Detroit to Chicago arrive on time 85% of the time across 12,641 flights. Here’s how each airline really performs.

0.0

On-time rate

12,641 flights

Airline	On-time	Flights
Southwest Airlines	87%	6,931
Delta Air Lines	84%	5,710

On-time = arrived within 15 minutes of schedule, per BTS TranStats. Compare the reverse leg MDW → DTW.

How to Pick a Reliable Flight (Not Just the Cheapest)

A practical checklist for booking the flight that gets you there — not just the cheap one.

Nonstop vs. Connecting Flights: The Reliability Trade-off

A stop multiplies the ways a trip can break. When it's worth it — and how to de-risk it.

Do Morning Flights Really Have Fewer Delays?

Yes — and there's a clear reason. How delays snowball through the day.

Are Some Airlines Really More Reliable Than Others?

The reliability gap between airlines is real — here's what actually drives it.

Score real DTW–MDW flights on reliability, weather, and connection safety — not just price.

Opens a partner site; we may earn a commission if you book there. It's a general fare search — nothing on it is scored.