Direct (nonstop) flights from Chicago to San Juan
1 airline flys nonstop from Chicago Midway International (MDW) to Luis Munoz Marin International (SJU). It's 2,056 miles (3,309 km), about 4h 40m in the air. Operated by Southwest Airlines.
Southwest Airlines
Route data last updated: May 29, 2026
Airlines with non-stop flights
WN
Southwest Airlines
Alternative Routes
Other ways to fly from Chicago to San Juan with one stop · direct emits 347 kg CO₂ per passenger
Looking for the return flight?
SJU → MDW: Flights from San Juan to ChicagoOther direct flights from Chicago
Direct flights from San Juan (SJU)
Frequently Asked Questions
How long is the direct flight from Chicago to San Juan?
A nonstop flight from Chicago (MDW) to San Juan (SJU) takes approximately 4 hours and 40 minutes. The distance is 2,056 miles (3,309 km).
Which airlines fly nonstop from Chicago to San Juan?
Just Southwest Airlines.
Is there a nonstop flight from Chicago to San Juan?
Yes. 1 airline: Southwest Airlines.
How far is Chicago from San Juan?
The flight distance from Chicago to San Juan is 2,056 miles (3,309 km), measured as the great-circle (shortest air) distance. That's roughly the same distance as New York to Los Angeles.
What is the time difference between Chicago and San Juan?
San Juan is 1 hour ahead of Chicago. (America/Chicago vs America/Puerto_Rico.)
What type of aircraft flies from Chicago to San Juan?
At 4h 40m, this route typically uses narrow-body or mid-range jets — Boeing 737 MAX or Airbus A320neo. Varies by airline.
Do I need a visa to travel from USA to Puerto Rico?
Depends on your passport. Check with the Puerto Rico embassy or an official visa portal before booking — requirements change.
What is the carbon footprint of a flight from Chicago to San Juan?
Roughly 347 kg CO2 per passenger one-way. That's about the same as driving 1,735 km.
Is the return flight from San Juan to Chicago also nonstop?
Yes — nonstop flights run both ways. Flight time may differ slightly due to wind patterns.
When is the cheapest time to fly from Chicago to San Juan?
Midweek flights (Tue/Wed) outside holiday peaks are usually cheapest. 3-6 weeks ahead is a good window for this route. Use "Check Prices" above to compare.
How early should I arrive at Chicago Midway International for this flight?
3 hours before departure for international flights. You need time for check-in, security, and immigration.