Chicago (MDW) to San Juan (SJU) flights
Southwest Airlines flies nonstop from Chicago Midway International Airport to Luis Munoz Marin International Airport, with about 2 flights a week in July 2026. The 2,057-mile flight takes about 4h 37m gate to gate.
- Distance
- 2,057 mi · 3,310 km
- Flight time
- 4h 37m
- Airlines
- 1
- Seats filled
- 93%
Airlines flying MDW to SJU
| Airline | Flights a week | Aircraft | Passengers (12 months) | Flight time |
|---|---|---|---|---|
| Southwest Airlines | 2 | Boeing 737 MAX 8, Boeing 737-700 / MAX 7, Boeing 737-800 | 7,761 | 4h 37m |
Airlines are the operating carrier: regional airlines such as SkyWest or Horizon often fly under a larger airline's brand.
Is MDW to SJU on time?
From September 2025 to August 2026, 67% of 53 flights arrived within 15 minutes of schedule and 1.9% were cancelled. Flights leaving around 7am were the most punctual (75%), those around 8am the least (64%). Most delay time was caused by the airline (crew, maintenance, cleaning, fuelling) (38%).
| Airline | Flights | On time | Average delay | Cancelled |
|---|---|---|---|---|
| Southwest Airlines | 53 | 67% | 17 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
Flights by month
| Month | Flights | Flights, relative | Passengers |
|---|---|---|---|
| August 2025 | 2 | 309 | |
| November 2025 | 4 | 603 | |
| December 2025 | 4 | 663 | |
| January 2026 | 4 | 614 | |
| February 2026 | 4 | 638 | |
| March 2026 | 8 | 1,175 | |
| April 2026 | 5 | 769 | |
| May 2026 | 5 | 856 | |
| June 2026 | 8 | 1,044 | |
| July 2026 | 8 | 1,090 |
Related
Source: US Department of Transportation, T-100 Segment data, August 2025 to July 2026.