Direct flights from Chicago to San Juan ORD → SJU
American Airlines, Frontier Airlines, Southwest Airlines, Spirit Airlines and United Airlines operate nonstop flights from Chicago (ORD) to San Juan (SJU). The nonstop flight takes around ~4h 10m, covering 2,074 miles (3,338 km) and operates multiple daily. Round-trip fares currently start at $183, with a typical fare around $472 across 79 recent fare combinations. Updated 28 June 2026.
60-day flexibility overview based on 79 recent fares across the next 60 days
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American Airlines
AA
Frontier Airlines
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United Airlines
UA
Departure Schedule next 7 days
Scheduled departures over the next 7 days · Updated 1d ago
American Airlines
Frontier Airlines
United Airlines
Frequently asked questions
Is there a direct flight from Chicago to San Juan?
Yes, American Airlines, Frontier Airlines and 3 more airlines operate nonstop flights from Chicago (ORD) to San Juan (SJU).
Which airlines fly direct from Chicago to San Juan?
American Airlines, Frontier Airlines, Southwest Airlines, Spirit Airlines, United Airlines operate nonstop flights from Chicago to San Juan.
How long is the flight from Chicago to San Juan?
The nonstop flight from Chicago to San Juan takes ~4h 10m (approximately 3338 km).
How often do direct flights operate from Chicago to San Juan?
Nonstop flights from Chicago to San Juan operate multiple daily.
How much is a round-trip flight from Chicago to San Juan?
Round-trip flights from Chicago (ORD) to San Juan (SJU) start at $183, with a typical fare around $472. Based on 79 recent fare combinations.