Likely delayed: there are delays at WN 585's airports as of 6:46 PM ET. It arrived on time 72.2% of the time in June-August 2026. When it was late, the average delay was 42 minutes. None were cancelled. AUS has major delays (runway construction, max 3 hours and 3 minutes), so this flight is likely to be delayed.
High cancellation risk
Leg 3 of 3 (BOS → MDW): Next leg BOS → MDW, scheduled 10:05 PM local time. No delays at BOS right now. This flight number flew about 3 days a week in June-August 2026, so it may not operate today. Line up a backup option.
0% of its flights were cancelled in June-August 2026; AUS has major delays; rough weather at AUS.
Estimate from the schedule, live position and airport conditions, if this flight operates today. Check Southwest for official times.
Book a backup seat BNA → MDWThis flight is cancelled often; a refundable backup costs little
What to do now
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Route and schedule
| Leg | Scheduled | On time |
|---|---|---|
| BNA → MKE Nashville, TN to Milwaukee, WI | 8:10 AM → 9:45 AM | 88% |
| AUS → DAL Austin, TX to Dallas, TX | 12:25 PM → 1:30 PM | 83% |
| BOS → MDW Boston, MA to Chicago, IL | 10:05 PM → 11:50 PM | 11% |
Local times. Schedules change; check your booking.
How reliable is WN 585?
| Arrived on time (within 15 min) | 72.2% |
| Average delay when late | 42 min |
| Cancelled | 0% |
| Diverted | 0% |
| Flights tracked | 115 |
Best and worst days to fly WN 585
WN 585 was most reliable on Tuesdays (100% on time) and least reliable on Sundays (27%).
| Monday | |
| Tuesday | |
| Wednesday | |
| Thursday | |
| Friday | |
| Saturday | |
| Sunday |
Why it runs late
| Late-arriving plane | |
| Airline (crew, maintenance) | |
| Air traffic system | |
| Extreme weather |
Share of delay minutes by cause, as reported by Southwest to the Department of Transportation.
Other flights BNA → MKE
All flights on this route, ranked
Live status at its airports
We show airport-wide airport status, not this flight's gate or live position. For that, check the Southwest app.
Southwest delays and what you're owed · Airline phone numbers
About this data
On-time history: U.S. Bureau of Transportation Statistics, Reporting Carrier On-Time Performance, June-August 2026. Live conditions: live airport status. "On time" means arriving within 15 minutes of schedule.
Common questions
Is WN 585 delayed today?
AUS has major delays (runway construction, max 3 hours and 3 minutes), so this flight is likely to be delayed. Checked 6:46 PM ET. For this flight's gate and exact status, check the Southwest app.
Is WN 585 usually on time?
WN 585 arrived within 15 minutes of schedule 72.2% of the time in June-August 2026, with an average delay of 42 minutes when late.
How often is WN 585 cancelled?
0% of WN 585 flights were cancelled in June-August 2026.