| Date | From | To | Departure | Arrival | Status | |
|---|---|---|---|---|---|---|
| Sep 17 | BOS | MDW | 09:46 | 11:00 |
Delayed
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Track > |
| Sep 16 | BOS | MDW | 07:43 | 09:09 |
Landed
|
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| Sep 15 | BOS | MDW | 07:40 | 08:45 |
Landed
|
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| Sep 14 | BOS | MDW | 07:39 | 08:49 |
Landed
|
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| Sep 13 | BOS | MDW | 07:40 | 08:54 |
Landed
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| Sep 12 | BOS | MDW | 07:18 | 08:23 |
Landed
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| Sep 11 | BOS | MDW | 07:43 | 08:54 |
Landed
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| Sep 10 | BOS | MDW | 07:38 | 08:59 |
Landed
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| Sep 09 | BOS | MDW | 07:38 | 08:47 |
Landed
|
Track > |
| Sep 08 | BOS | MDW | 07:43 | 08:53 |
Landed
|
Track > |
Southwest Airlines Flight WN744 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 WN744 flight from Boston to Chicago?
The average flight time from Boston to Chicago is 2 hours and 12 minutes. The flight distance is 1381 km / 858 miles and the average flight speed is 627 km/h / 390 mph.
How many WN744 flights are operated per week?
6 flights per week. The flight WN744 is operated on Monday, Tuesday, Wednesday, Thursday, Saturday and Sunday.
What is the On-Time Performance (OTP) of Southwest Airlines Flight WN744 Boston to Chicago?
The Airportia On-Time Performance Rating for Southwest Airlines Flight WN744 is 4.8/5 stars. This metric is calculated using data from the past 10 flights.
When was the latest WN744 flight?
The latest flight took off on Thursday, September 17th, 2026 with the flight status being En-Route on 11:00.
How else can the flight WN744 be referenced as?
This Southwest Airlines flight can also be referenced as SWA744, WN0744, WN 744, SWA 744.
How often is flight WN744 delayed?
On average, 20% of all WN744 flights are delayed. The average delay is 59 minutes.
Can I get compensation for my delayed or cancelled WN744 flight or baggage issues?
If your WN744 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 WN744 Flight Tracker above for more details.
Other flights departing from Boston BOS: DL2570, UA570, DL977, AA1259
Other flights arriving at Chicago MDW: WN2371, WN486, WN3382, WN3556
All flights connecting Boston BOS to Chicago MDW.