Quick Facts: Chicago to San Juan
- Average Fare
- $721
- 5-Year Average
- $579
- Lowest Recorded
- $290
- Flight Time
- 4h 40m
- Distance
- 3,337 km
- Best Quarter
- Q3 (Jul-Sep)
- Price Trend
- rising
- Data Source
- T-100
Route Traffic Data
Traffic data from BTS T-100 International; prices estimated based on distance and market factors.
Search Flights
Avg. $721Compare prices across booking sites. Prices vary by date and availability.
About Chicago to San Juan Flights
Discover the best flights from Chicago to San Juan, covering 3,337 km in approximately 4h 40m. Chicago (ORD) to San Juan (SJU) is one of the popular medium-haul routes connecting United States and Puerto Rico. With 7 major airlines operating this route including direct flights, travelers have plenty of options to choose from. Whether you're traveling for business or leisure, our comprehensive guide helps you find the best deals, understand seasonal price variations, and choose the right airline for your journey from Chicago to San Juan.
Price Trend Estimate
T-100 TrafficBest Time to Fly
Best Quarter
Q3 (Jul-Sep)
Lowest average fares
Peak Season
Q1 (Jan-Mar)
Highest average fares
Book in Advance
99 days
For best prices
Price Analysis
Current prices are 25% above 5-year average. The best time to book flights from Chicago to San Juan is during Q3 (Jul-Sep).
Booking Tips
For the best prices on Chicago to San Juan flights, we recommend booking 138 days in advance. International flights typically see price increases as the departure date approaches, so early booking is advisable. Tuesday and Wednesday departures often offer the lowest fares, while Friday and Sunday flights tend to be more expensive due to business and leisure travel demand. Consider flying early morning or late evening for additional savings, as these off-peak times usually have lower demand.
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Airlines Serving This Route
Prices shown are estimates based on historical data. Actual prices may vary based on dates, availability, and current promotions.
Alternative Flight Options
Milwaukee → San Juan
Milwaukee Mitchell International (MKE) to Luis Muñoz Marín International (SJU)
Distance: 3,414 km
Average price: $796
Chicago → San Juan
Chicago Midway International (MDW) to Luis Muñoz Marín International (SJU)
Distance: 3,314 km
Average price: $776
Chicago → San Juan
Chicago Midway International (MDW) to Luis Muñoz Marín International (SJU)
Distance: 3,314 km
Average price: $776
Chicago → St. Thomas
O'Hare International (ORD) to Cyril E. King Airport (STT)
Distance: 3,408 km
Average price: $795
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Frequently Asked Questions
How long is the flight from Chicago to San Juan?
The flight time from Chicago (ORD) to San Juan (SJU) is approximately 4 hours and 40 minutes. This duration is for direct flights and may vary depending on aircraft type, weather conditions, and air traffic.
What is the distance between Chicago and San Juan?
The aerial distance between Chicago and San Juan is 3,337 kilometers (2,074 miles). This is the straight-line distance, which is used to calculate flight times.
Which airlines fly from Chicago to San Juan?
Several airlines operate flights between Chicago and San Juan, including American Airlines, United Airlines, SkyWest Airlines and 4 more airlines. Direct flights are available on this route.
What is the cheapest month to fly from Chicago to San Juan?
Based on historical data, February typically offers the lowest airfares for flights from Chicago to San Juan. However, prices can vary based on holidays, events, and airline promotions. We recommend checking our price calendar for the most up-to-date information.
How far in advance should I book my flight to San Juan?
For the best prices on Chicago to San Juan flights, we recommend booking 141 days in advance. International flights generally require earlier booking than domestic routes.
Do I need a visa to travel from Chicago to San Juan?
Visa requirements depend on your nationality and the purpose of your visit. Citizens of United States traveling to Puerto Rico should check the latest visa requirements. Visit our partner site visarequirements.io for detailed visa information.
What is the time difference between Chicago and San Juan?
Chicago operates on America/Chicago time zone, while San Juan is in the America/Puerto_Rico time zone. For current time differences and to plan your schedule, visit our partner site timezig.com for accurate timezone conversions.