| Date | From | To | Departure | Arrival | Status | |
|---|---|---|---|---|---|---|
| Sep 29 | BOS | MDW | 22:16 | 23:20 |
Delayed
|
Track > |
| Sep 26 | BOS | MDW | 22:03 | 23:00 |
Delayed
|
Track > |
| Sep 25 | BOS | MDW | 20:20 | 21:55 |
Cancelled
|
Track > |
| Claim > | ||||||
| Sep 22 | BOS | MDW | 20:36 | 21:45 |
Landed
|
Track > |
| Sep 19 | BOS | MDW | 21:37 | 22:38 |
Landed Late
|
Track > |
| Sep 18 | BOS | MDW | 21:02 | 22:05 |
Landed
|
Track > |
| Sep 15 | BOS | MDW | 23:12 | 00:17 |
Delayed
|
Track > |
| Sep 12 | BOS | MDW | 21:19 | 22:15 |
Landed Late
|
Track > |
| Sep 11 | BOS | MDW | 22:39 | 23:43 |
Delayed
|
Track > |
| Sep 08 | BOS | MDW | 21:16 | 22:19 |
Landed Late
|
Track > |
Southwest Airlines Flight WN1440 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 WN1440 flight from Boston to Chicago?
The average flight time from Boston to Chicago is 2 hours and 2 minutes. The flight distance is 1381 km / 858 miles and the average flight speed is 663 km/h / 412 mph.
What is the On-Time Performance (OTP) of Southwest Airlines Flight WN1440 Boston to Chicago?
The Airportia On-Time Performance Rating for Southwest Airlines Flight WN1440 is 4.2/5 stars. This metric is calculated using data from the past 10 flights.
When was the latest WN1440 flight?
The latest flight took off on Tuesday, September 30th, 2025 with the flight status being En-Route on 23:20.
How else can the flight WN1440 be referenced as?
This Southwest Airlines flight can also be referenced as SWA1440, WN 1440, SWA 1440.
How often is flight WN1440 delayed?
On average, 80% of all WN1440 flights are delayed. The average delay is 62 minutes.
Can I get compensation for my delayed or cancelled WN1440 flight or baggage issues?
If your WN1440 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 WN1440 Flight Tracker above for more details.
Other flights departing from Boston BOS: AA3295, UA688, AS249, AA1004
Other flights arriving at Chicago MDW: WN3411, WN1801, WN3138, WN3180
All flights connecting Boston BOS to Chicago MDW.
