| Date | From | To | Departure | Arrival | Status | |
|---|---|---|---|---|---|---|
| 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 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.
How long is the WN1585 flight from Boston to Chicago?
The average flight time from Boston to Chicago is 2 hours and 6 minutes. The flight distance is 1381 km / 858 miles and the average flight speed is 658 km/h / 409 mph.
How many WN1585 flights are operated per week?
1 flight per week. The flight WN1585 is operated on Sunday.
What is the On-Time Performance (OTP) of Southwest Airlines Flight WN1585 Boston to Chicago?
The Airportia On-Time Performance Rating for Southwest Airlines Flight WN1585 is 5/5 stars. This metric is calculated using data from the past 10 flights.
When was the latest WN1585 flight?
The latest flight took off on Sunday, September 27th, 2026 with the flight status being Landed on 10:46.
How else can the flight WN1585 be referenced as?
This Southwest Airlines flight can also be referenced as SWA1585, WN 1585, SWA 1585.
How often is flight WN1585 delayed?
On average, 12% of all WN1585 flights are delayed. The average delay is 18 minutes.
Can I get compensation for my delayed or cancelled WN1585 flight or baggage issues?
If your WN1585 flight was cancelled, delayed, or if you experienced baggage issues such as delayed, damaged, or lost bags, you may be entitled to compensation. Compensation amounts and eligibility depend on various regulations, including EC 261/2004, UK261, CA Montreal Convention, US GoodWill, BR-ANAC, SA-GACA and TK-SHY.
See our WN1585 Flight Tracker above for more details.
Other flights departing from Boston BOS: UA726, UA1349, AA479, AA2788
Other flights arriving at Chicago MDW: WN298, WN562, WN1822, PD2387
All flights connecting Boston BOS to Chicago MDW.