| Date | From | To | Departure | Arrival | Status | |
|---|---|---|---|---|---|---|
| Jan 04 | MCO | MDW | 17:45 | 19:09 |
Landed
|
Track > |
| Jan 03 | MCO | MDW | 15:36 | 17:06 |
Landed
|
Track > |
| Jan 02 | MCO | MDW | 18:14 | 19:38 |
Landed Late
|
Track > |
| Dec 30 | MCO | MDW | 20:28 | 21:56 |
Delayed
|
Track > |
| Dec 29 | MCO | MDW | 18:50 | 20:13 |
Delayed
|
Track > |
| Dec 28 | MCO | MDW | 18:10 | 19:24 |
Landed
|
Track > |
| Dec 27 | MCO | MDW | 15:36 | 17:09 |
Landed
|
Track > |
| Dec 26 | MCO | MDW | 20:27 | 21:54 |
Delayed
|
Track > |
| Dec 23 | MCO | MDW | 17:50 | 19:22 |
Landed
|
Track > |
| Dec 22 | MCO | MDW | 17:54 | 19:19 |
Landed
|
Track > |
Southwest Airlines Flight WN2299 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 WN2299 flight from Orlando to Chicago?
The average flight time from Orlando to Chicago is 2 hours and 26 minutes. The flight distance is 1595 km / 991 miles and the average flight speed is 656 km/h / 408 mph.
What is the On-Time Performance (OTP) of Southwest Airlines Flight WN2299 Orlando to Chicago?
The Airportia On-Time Performance Rating for Southwest Airlines Flight WN2299 is 4.3/5 stars. This metric is calculated using data from the past 10 flights.
Which terminal is the flight WN2299 arriving at?
Flight WN2299 arrives at Chicago Midway International Airport (MDW) Terminal E.
When was the latest WN2299 flight?
The latest flight took off on Monday, January 5th, 2026 with the flight status being Landed on 19:09.
How else can the flight WN2299 be referenced as?
This Southwest Airlines flight can also be referenced as SWA2299, WN 2299, SWA 2299.
How often is flight WN2299 delayed?
On average, 90% of all WN2299 flights are delayed. The average delay is 49 minutes.
Can I get compensation for my delayed or cancelled WN2299 flight or baggage issues?
If your WN2299 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 WN2299 Flight Tracker above for more details.
Other flights departing from Orlando MCO: DL5797, WN3634, NK397, WN4266
Other flights arriving at Chicago MDW: WN1939, WN2278, WN3070, WN1245
All flights connecting Orlando MCO to Chicago MDW.