Chicago to San Juan (MDW–SJU) — Airlines, Schedules & Connections
No flights match your filters.
No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.
Most recently operated nonstop flights — the month shown is when each was last scheduled. Most destinations remain reachable with a connection.
No discontinued nonstop flights on record for this route.
MDW–SJU is served by 1 airline with nonstop service. Southwest Airlines leads the route. The flight covers 2,059 miles in approximately 4h 45m. Beyond nonstop, 1-stop connecting options are also available.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| WN Southwest Airlines | 2 | 737, 7S7 | 4h40-4h50 | – | – |
Weekly Schedule Pattern
Connection Landscape
On-Time Performance
Other ways to reach San Juan from Chicago
| Metric | MDW→SJU | ORD→SJU |
|---|---|---|
| Distance from MDW | – | 15 mi |
| Nonstop airlines | 1 | 5 |
| Weekly flights | 2 | 28 |
| Flight time | 4h 45m | 4h 39m |
| Departure OTP | 54% | – |
Travel Essentials
MDW: CDT · SJU: AST
When it's 6:00 PM in Chicago, it's 7:00 PM in San Juan.
Puerto Rico is an unincorporated US territory. US citizens travel to Puerto Rico with the same freedom as traveling between US states. No passport is needed. A valid government-issued photo ID (driver's license or state ID) is sufficient. There are no immigration or customs formalities for domestic travelers. At Luis Munoz Marin International Airport (SJU) in San Juan, you walk off the plane and collect your luggage with no border checkpoint.
Puerto Rico uses US currency, US federal law, and the US Postal Service. Your US health insurance, driver's license, and cell phone plan work here. Mail delivery uses standard US ZIP codes (006xx to 009xx). Puerto Rico is in the Atlantic Standard Time zone (AST), UTC-4, which is 1 hour ahead of US Eastern Time during daylight saving time and the same as Eastern during standard time (Puerto Rico does not observe daylight saving). Old San Juan's colonial architecture, the El Yunque National Rainforest (the only tropical rainforest in the US National Forest System), and Flamenco Beach on Culebra are the top draws.
Direct flights from New York JFK to San Juan run about 3 hours 30 minutes on JetBlue, Delta, United, and Spirit. Miami to SJU runs about 2 hours 30 minutes. Fort Lauderdale, Orlando, Atlanta, Philadelphia, Chicago, Dallas, and dozens of other US cities have nonstop service. SJU is the busiest airport in the Caribbean and a hub for flights to the US Virgin Islands, the Eastern Caribbean, and South America. Because this is a domestic flight, no TSA PreCheck or Global Entry distinctions apply beyond what you use on any US domestic flight. Car rental starts at $30 per day. The Tren Urbano metro runs a single line from Bayamon to Sagrado Corazon in Santurce for $0.75 per ride. AMA buses cover the San Juan metro area at $0.75.
MDW–SJU Quick Facts
Frequently Asked Questions
Flights from MDW to SJU
Chicago Midway International Airport (MDW) and Luis Munoz Marin International Airport (SJU) are connected by nonstop service from Southwest Airlines. With 2 weekly departures, this is a regularly served route.
MDW to SJU Flight Duration and Schedule
Nonstop flight time from MDW to SJU is about 4 hours 45 minutes gate to gate. The route covers a distance of 2,059 miles (3,314 km). There are approximately 2 weekly flights outbound and 3 return, totaling 5 flights per week in both directions.
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via Nashville, Orlando and Tampa. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD).