| Date | From | To | Departure | Arrival | Status | |
|---|---|---|---|---|---|---|
| Aug 03 | MCO | MDW | 20:57 | 22:27 |
Landed Late
|
Track > |
| Jul 27 | MCO | MDW | 20:42 | 21:59 |
Landed
|
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| Jul 20 | MCO | MDW | 21:22 | 22:51 |
Landed Late
|
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| Jul 13 | MCO | MDW | 20:42 | 22:06 |
Landed Late
|
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| Jul 06 | MCO | MDW | 20:32 | 21:50 |
Landed
|
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| Jun 29 | MCO | MDW | 20:31 | 21:51 |
Landed
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| Jun 22 | MCO | MDW | 20:48 | 22:06 |
Landed Late
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| Jun 15 | MCO | MDW | 20:53 | 22:08 |
Landed Late
|
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| Jun 08 | MCO | MDW | 20:39 | 21:57 |
Landed
|
Track > |
Southwest Airlines Flight WN255 connects Orlando, United States to Chicago, United States, taking off from Orlando International Airport MCO and landing at Chicago Midway International Airport MDW.
How long is the WN255 flight from Orlando to Chicago?
The average flight time from Orlando to Chicago is 2 hours and 21 minutes. The flight distance is 1595 km / 991 miles and the average flight speed is 680 km/h / 422 mph.
What is the On-Time Performance (OTP) of Southwest Airlines Flight WN255 Orlando to Chicago?
The Airportia On-Time Performance Rating for Southwest Airlines Flight WN255 is 4.7/5 stars. This metric is calculated using data from the past 10 flights.
When was the latest WN255 flight?
The latest flight took off on Monday, August 4th, 2025 with the flight status being Landed on 22:27.
How else can the flight WN255 be referenced as?
This Southwest Airlines flight can also be referenced as SWA255, WN0255, WN 255, SWA 255.
How often is flight WN255 delayed?
On average, 89% of all WN255 flights are delayed. The average delay is 20 minutes.
Can I get compensation for my delayed or cancelled WN255 flight or baggage issues?
If your WN255 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 WN255 Flight Tracker above for more details.
Other flights departing from Orlando MCO: WN1772, WN2281, NK1526, NK1245
Other flights arriving at Chicago MDW: WN2773, WN4828, WN1860, WN1665
All flights connecting Orlando MCO to Chicago MDW.
