Direct (nonstop) flights from San Juan to Chicago
1 airline flys nonstop from Luis Munoz Marin International (SJU) to Chicago Midway International (MDW). It's 2,056 miles (3,309 km), about 4h 50m 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 San Juan to Chicago with one stop · direct emits 347 kg CO₂ per passenger
Looking for the return flight?
MDW → SJU: Flights from Chicago to San JuanOther direct flights from San Juan
Direct flights from Chicago (MDW)
Frequently Asked Questions
How long is the direct flight from San Juan to Chicago?
A nonstop flight from San Juan (SJU) to Chicago (MDW) takes approximately 4 hours and 50 minutes. The distance is 2,056 miles (3,309 km).
Which airlines fly nonstop from San Juan to Chicago?
Just Southwest Airlines.
Is there a nonstop flight from San Juan to Chicago?
Yes. 1 airline: Southwest Airlines.
How far is San Juan from Chicago?
The flight distance from San Juan to Chicago 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 San Juan and Chicago?
Chicago is 1 hour behind San Juan. (America/Puerto_Rico vs America/Chicago.)
What type of aircraft flies from San Juan to Chicago?
At 4h 50m, 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 Puerto Rico to USA?
Depends on your passport. Check with the USA embassy or an official visa portal before booking — requirements change.
What is the carbon footprint of a flight from San Juan to Chicago?
Roughly 347 kg CO2 per passenger one-way. That's about the same as driving 1,735 km.
Is the return flight from Chicago to San Juan 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 San Juan to Chicago?
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 Luis Munoz Marin International for this flight?
3 hours before departure for international flights. You need time for check-in, security, and immigration.