San Juan (SJU) to Chicago (MDW) flights
Southwest Airlines flies nonstop from Luis Munoz Marin International Airport to Chicago Midway International Airport, with about 2 flights a week in July 2026. The 2,057-mile flight takes about 5h 1m gate to gate.
- Distance
- 2,057 mi · 3,310 km
- Flight time
- 5h 1m
- Airlines
- 1
- Seats filled
- 90%
Airlines flying SJU to MDW
| Airline | Flights a week | Aircraft | Passengers (12 months) | Flight time |
|---|---|---|---|---|
| Southwest Airlines | 2 | Boeing 737 MAX 8, Boeing 737-800, Boeing 737-700 / MAX 7 | 7,714 | 5h 1m |
Airlines are the operating carrier: regional airlines such as SkyWest or Horizon often fly under a larger airline's brand.
Is SJU to MDW on time?
From September 2025 to August 2026, 63% of 53 flights arrived within 15 minutes of schedule and 1.9% were cancelled. Flights leaving around 2pm were the most punctual (62%), those around 4pm the least (42%). Most delay time was caused by late-arriving aircraft (74%).
| Airline | Flights | On time | Average delay | Cancelled |
|---|---|---|---|---|
| Southwest Airlines | 53 | 63% | 20 min | 1.9% |
Airlines as sold: flights operated by regional partners count under the airline on the ticket. Average delay is across all completed flights, early arrivals counted as zero.
On-time arrivals by departure time
| Scheduled departure | Flights | On time, relative | On time |
|---|---|---|---|
| 2pm to 3pm | 13 | 62% | |
| 3pm to 4pm | 11 | 60% | |
| 4pm to 5pm | 12 | 42% |
Flights by month
| Month | Flights | Flights, relative | Passengers |
|---|---|---|---|
| August 2025 | 2 | 330 | |
| November 2025 | 4 | 530 | |
| December 2025 | 4 | 532 | |
| January 2026 | 4 | 527 | |
| February 2026 | 4 | 519 | |
| March 2026 | 8 | 1,198 | |
| April 2026 | 5 | 774 | |
| May 2026 | 5 | 840 | |
| June 2026 | 8 | 1,286 | |
| July 2026 | 7 | 1,178 |
Related
Source: US Department of Transportation, T-100 Segment data, August 2025 to July 2026.