| Date | From | To | Departure | Arrival | Status | |
|---|---|---|---|---|---|---|
| Jan 01 | MCO | MDW | 16:48 | 18:20 |
Landed
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Track > |
| Dec 31 | MCO | MDW | 16:53 | 18:30 |
Landed
|
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| Dec 25 | MCO | MDW | 16:39 | 18:04 |
Landed
|
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| Dec 24 | MCO | MDW | 16:46 | 18:19 |
Landed
|
Track > |
| Dec 17 | MCO | MDW | 16:50 | 18:13 |
Landed
|
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| Dec 16 | MCO | MDW | 16:50 | 18:17 |
Landed
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| Dec 15 | MCO | MDW | 18:11 | 19:29 |
Delayed
|
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| Dec 13 | MCO | MDW | 16:27 | 17:52 |
Landed
|
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| Dec 11 | MCO | MDW | 16:46 | 18:23 |
Landed
|
Track > |
| Dec 10 | MCO | MDW | 16:45 | 18:07 |
Landed
|
Track > |
Southwest Airlines Flight WN1550 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 WN1550 flight from Orlando to Chicago?
The average flight time from Orlando to Chicago is 2 hours and 27 minutes. The flight distance is 1595 km / 991 miles and the average flight speed is 648 km/h / 403 mph.
What is the On-Time Performance (OTP) of Southwest Airlines Flight WN1550 Orlando to Chicago?
The Airportia On-Time Performance Rating for Southwest Airlines Flight WN1550 is 4.9/5 stars. This metric is calculated using data from the past 10 flights.
When was the latest WN1550 flight?
The latest flight took off on Friday, January 2nd, 2026 with the flight status being Landed on 18:20.
How else can the flight WN1550 be referenced as?
This Southwest Airlines flight can also be referenced as SWA1550, WN 1550, SWA 1550.
How often is flight WN1550 delayed?
On average, 20% of all WN1550 flights are delayed. The average delay is 34 minutes.
Can I get compensation for my delayed or cancelled WN1550 flight or baggage issues?
If your WN1550 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 WN1550 Flight Tracker above for more details.
Other flights departing from Orlando MCO: F91760, DL482, WN1742, NK516
Other flights arriving at Chicago MDW: WN1008, WN2291, WN3289, WN2774
All flights connecting Orlando MCO to Chicago MDW.