Cheap flights from San Juan to Chicago
Cheapest current fares: $136 in August 2026, 3,338 km direct flight in ~3h 56m.
Cheapest month-by-month fares
Lowest available fare per calendar month from San Juan (SJU) to Chicago (ORD). Refreshed daily.
San Juan (SJU) → Chicago (ORD)
- August 2026 $136
- September 2026 $174
- October 2026 $193
- June 2026 $195
- May 2026 $277
Frequently asked questions
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What is the cheapest month to fly from San Juan to Chicago?
Based on current 6-month forward fare data, August 2026 is the cheapest month to fly from San Juan (SJU) to Chicago (ORD), with fares starting from $136.
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What is the lowest current fare from SJU to ORD?
The lowest currently-listed fare from San Juan (SJU) to Chicago (ORD) is $136 on 2026-08-17.
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How long is the flight from San Juan to Chicago?
Direct flights from SJU to ORD cover approximately 3,338 km (2,074 miles), with an estimated flight time of 3h 56m. Operating airlines: AA, F9, NK, UA, WN.
Related guides for this route
Sibling pages — full route detail, airport overviews, visa context, per-airline routes.