San Juan (SJU) → Chicago (ORD)
About San Juan to Chicago Flights
Discover the best flights from San Juan to Chicago, covering 3,337 km in approximately 4h 40m. San Juan (SJU) to Chicago (ORD) is one of the popular medium-haul routes connecting Puerto Rico and United States. 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 San Juan to Chicago.
12-Month Price History
Flight prices from San Juan to Chicago vary significantly throughout the year. February typically offers the best deals with average prices around $677, while July sees the highest prices, averaging $1151. Savvy travelers can save up to 41% by choosing their travel dates wisely.
Best Time to Fly
Cheapest Month
February
Save up to 40% on average
Most Expensive
July
Peak season pricing
Book in Advance
167 days
For best prices
Booking Tips
For the best prices on San Juan to Chicago flights, we recommend booking 132 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.
Airlines Serving This Route
| Airline | Economy | Business | First |
|---|---|---|---|
Delta Air Lines DL | $1140 | $5230 | $6300 |
SkyWest Airlines OO | $1200 | $4710 | $6930 |
Kalitta Air K4 | $1230 | $4250 | $6630 |
United Airlines UA | $1330 | $4650 | $5830 |
British Airways BA | $1370 | $4910 | $8260 |
Air France AF | $1420 | $4500 | $7580 |
American Airlines AA | $1450 | $4970 | $5920 |
Delta Air Lines
DL
Economy
$1140
Business
$5230
First
$6300
SkyWest Airlines
OO
Economy
$1200
Business
$4710
First
$6930
Kalitta Air
K4
Economy
$1230
Business
$4250
First
$6630
United Airlines
UA
Economy
$1330
Business
$4650
First
$5830
British Airways
BA
Economy
$1370
Business
$4910
First
$8260
Air France
AF
Economy
$1420
Business
$4500
First
$7580
American Airlines
AA
Economy
$1450
Business
$4970
First
$5920
Prices shown are estimates based on historical data. Actual prices may vary based on dates, availability, and current promotions.
Alternative Flight Options
San Juan → Milwaukee
Luis Muñoz Marín International (SJU) to Milwaukee Mitchell International (MKE)
Distance: 3,414 km
Average price: $796
San Juan → Chicago
Luis Muñoz Marín International (SJU) to Chicago Midway International (MDW)
Distance: 3,314 km
Average price: $776
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Frequently Asked Questions
How long is the flight from San Juan to Chicago?
The flight time from San Juan (SJU) to Chicago (ORD) 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 San Juan and Chicago?
The aerial distance between San Juan and Chicago is 3,337 kilometers (2,074 miles). This is the straight-line distance, which is used to calculate flight times.
Which airlines fly from San Juan to Chicago?
Several airlines operate flights between San Juan and Chicago, 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 San Juan to Chicago?
Based on historical data, February typically offers the lowest airfares for flights from San Juan to Chicago. 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 Chicago?
For the best prices on San Juan to Chicago flights, we recommend booking 109 days in advance. International flights generally require earlier booking than domestic routes.
Do I need a visa to travel from San Juan to Chicago?
Visa requirements depend on your nationality and the purpose of your visit. Citizens of Puerto Rico traveling to United States should check the latest visa requirements. Visit our partner site visarequirements.io for detailed visa information.
What is the time difference between San Juan and Chicago?
San Juan operates on America/Puerto_Rico time zone, while Chicago is in the America/Chicago time zone. For current time differences and to plan your schedule, visit our partner site timezig.com for accurate timezone conversions.