WN1585 Flight Status Southwest Airlines: Boston to Chicago (SWA1585)
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WN 1585 Boston to Chicago Flight Status
Not scheduled today (November 14th, 2026). Latest flight: September 27th, 2026 ; recent history is in the table below.
- This flight continues to Nashville (BNA): WN1585 Chicago to Nashville departs at 11:40 local time on Sep 27.
WN 1585 Flight Status & Schedule Southwest Airlines Boston to Chicago
| Date | From | To | Departure | Arrival | Status | Details |
|---|---|---|---|---|---|---|
| Sep 27 | BOS | MDW | 09:45 | 10:46 | Landed | Track > |
| Sep 20 | BOS | MDW | 09:42 | 10:54 | Landed | Track > |
| Sep 13 | BOS | MDW | 09:44 | 10:53 | Landed | Track > |
| Sep 06 | BOS | MDW | 13:55 | 14:58 | Landed Late | Track > |
| Aug 30 | BOS | MDW | 09:41 | 10:55 | Landed | Track > |
| Aug 23 | BOS | MDW | 09:39 | 10:41 | Landed | Track > |
| Aug 16 | BOS | MDW | 09:36 | 10:41 | Landed | Track > |
| Aug 09 | BOS | MDW | 09:42 | 10:45 | Landed | Track > |
Southwest Airlines flight WN 1585 links Boston and Chicago, 1,381 km (858 mi) apart. Its timetable allows 2 h 35 min; in practice it usually takes about 2 h 5 min, so it often makes up time. It is not flying today; the last flight, on 27 September 2026, landed on time.
About WN 1585
Southwest Airlines Flight WN1585 connects Boston, United States to Chicago, United States, taking off from Boston Logan International Airport BOS and landing at Chicago Midway International Airport MDW.
- Distance
- 1,381 km (858 mi)
- Typical flight time
- 2 h 5 min
- On time
- 7 of the last 8
- Average delay when late
- 18 min
- Usually departs from
- Terminal B
WN 1585 FAQ
- How long is the WN1585 flight from Boston to Chicago?
- The timetable allows 2 h 35 min. Boston to Chicago is 1,381 km (858 mi).
- How often is WN1585 from Boston to Chicago late?
- 1 of the last 8 flights arrived 15 or more minutes late; when late, by 18 minutes on average.
- When was the latest WN1585 flight from Boston to Chicago?
- The latest WN1585 was the 09:25 (local time) departure from Boston on 27 September 2026; it landed 14 minutes early.
- Which terminal does WN1585 use?
- It usually leaves from Terminal B at Boston Logan International Airport (BOS). Check the flight card above for today's terminal and gate.
- What other flight numbers does WN1585 have?
- Also listed as SWA1585 (Southwest Airlines' ICAO code) and WN 1585.
WN1585 and Boston BOS to Chicago MDW Flights
Other flights departing from Boston BOS: 9K2131, YX5693, AA2788, DL5778
Other flights arriving at Chicago MDW: WN298, WN256, WN1822
All flights connecting Boston BOS to Chicago MDW.