MDW to MKE flight delays
Chicago, IL (MDW) Milwaukee, WI (MKE) · 80 miles
236 flights · January 2025 – August 2026 · US Bureau of Transportation Statistics
67.69%
Arrived on time
Within 15 minutes of schedule
2.97%
Cancelled
Share of scheduled flights
58 min
When late, late by
Average across delayed arrivals
20 min
Delay per flight
Averaged over every flight flown
What the record says about this route
Cancellation, not delay, is the risk worth pricing here: 2.97% of scheduled flights never operated. A late flight still gets you there. A cancelled one leaves you rebooking, and on a route with few daily departures that can mean losing a day.
This is a late route. Flights from Chicago to Milwaukee miss their scheduled arrival often enough that a tight connection at the far end is a connection at risk.
Only Southwest Airlines flies this route in the published record, so there is no choice to weigh — the route's figures and the airline's are the same figures.
This is a thin route — 236 flights across the whole period. On a route this infrequent a cancellation is far more costly than the rate suggests, because the next departure may not be the same day.
Which airline should you fly on this route?
Over January 2025 – August 2026, Southwest Airlines arrived on time most often on MDW to MKE. Flights ran closest to schedule in May and worst in March.
Every airline on MDW to MKE
Ranked by how many flights each one operated. A carrier with fewer than 100 flights in the period is listed but not graded.
| Airline | Flights | On time | Cancelled | Avg delay | Grade |
|---|---|---|---|---|---|
| Southwest Airlines | 236 | 67.69% | 2.97% | 58 min | F |
Month by month
Share of flights that arrived within 15 minutes of schedule, by month flown.
The return leg
MKE to MDW Milwaukee back to Chicago 71.49% on time DOther routes from Chicago
Common questions
Are flights from Chicago to Milwaukee usually delayed?
67.69% of flights on the MDW to MKE route arrived within 15 minutes of schedule, so roughly 3 in every ten arrived late. That is worse than the average route in this record.
Which airlines fly from Chicago to Milwaukee?
Only Southwest Airlines appears in the published record on this route, with 236 flights and 67.69% arriving on time.
How often are MDW to MKE flights cancelled?
2.97% of scheduled flights did not operate — about 30 in every thousand. That is high enough that cancellation, not delay, is the risk worth planning around.
When MDW to MKE flights are late, how late are they?
About 58 minutes on average across the flights that arrived more than 15 minutes behind schedule.
What these figures do and do not tell you
Everything on this page is counted from the flights that actually operated on MDW to MKE during January 2025 – August 2026, as reported by the airlines to the US Bureau of Transportation Statistics. "On time" is the federal definition: arriving at the gate within 15 minutes of the scheduled time.
A route's record is a description of the past, not a forecast. Weather, air traffic control and the aircraft's earlier flights that day drive most delays, and none of them are predictable from a historical rate. What the record does tell you is whether this route runs late more often than others, and which carrier on it has the better history — which is the part you can actually act on when you book.
Cancellations are counted separately from delays because they are a different problem for a traveller: a late flight still gets you there. How the grade is calculated →