Flights from Chicago to San Juan
CHI
Chicago
15h 50m avg
SJU
San Juan
Flights from
$185
Compare 2 options across 2 airlines
Updated 3 months ago
$185
Cheapest Flight
$219
Average Price
1
Direct Flights
2
Airlines
Looking for the return flight? San Juan to Chicago from $269
SJU → CHI Flights
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2 of 2 flights
Airport Information
Key details about departure and arrival airports for this route
SJU
Luis Munoz Marin International Airport
City: San Juan
Country: PR
Type: Large Airport
Elevation: 9 ft
SJU Airport Guide →
Country: PR
Type: Large Airport
Elevation: 9 ft
Tips for Chicago to San Juan Flights
Save money and travel smarter with these route-specific tips
When to Book
Book CHI–SJU flights 6–8 weeks in advance for the best prices. Last-minute fares are typically 40–60% more expensive on this route.
Price Trends
The average fare is $219, but prices as low as $185 are available. That’s a potential saving of 27% compared to the most expensive option.
Direct vs Connecting
1 direct flight(s) available on this route
, starting from $253
. Direct flights save you 2–5 hours of travel time.
Flexible Dates
Flying midweek (Tuesday–Thursday) on CHI–SJU is typically 15–30% cheaper. Use our price comparison to spot the best day to fly.
Top Hotels in San Juan
Book accommodation at your destination — top-rated stays near SJU airport
Frequently Asked Questions
Everything you need to know about flying CHI to SJU
What is the cheapest flight from Chicago to San Juan?
The cheapest flight from Chicago (CHI) to San Juan (SJU) currently starts at $185 with AA. Prices are updated regularly and may vary by date and availability.
How many airlines fly from CHI to SJU?
We found 2 airline(s) operating on the CHI–SJU route, including AA, NK.
Are there direct flights from Chicago to San Juan?
Yes, there are 1 direct flight(s) available from CHI to SJU, with prices starting at $253.
What is the average flight price on this route?
The average flight price from Chicago to San Juan is approximately $219. Prices range from $185 to $253 depending on airline, time, and class.
How long is the flight from CHI to SJU?
The average flight duration from Chicago to San Juan is approximately 15 hours 50 minutes. Direct flights are typically shorter than connecting options.
What is the baggage allowance on CHI–SJU flights?
Baggage allowance varies by airline and fare class. Most economy fares on this route include 1 carry-on (7–8 kg) and 1 checked bag (20–23 kg). Always confirm baggage rules on the airline's site at booking — low-cost carriers may charge for checked bags.
From
$185
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