Flights from Chicago to San Juan from $185

Compare All CHI to SJU Flights

Prices are per person for one-way travel. Click “Book” to complete your reservation on the partner site.

2 of 2 flights

Airline	Schedule	Stops	Duration	Price
AA AA · 2984	05:00 CHI 20:50 SJU	0 stop(s)	15h 50m	$185 Best	Book →
NK NK · 2903	Schedule on partner site	Direct	—	$253	Book →

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 →

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

Casa Ciana

San Juan, 3.5★

10.0 Check Price

Palacio Provincial - Adults Only

San Juan, 3.5★

10.0 Check Price

Digital Nomad San Agustin Apartments

Andalucia Guest House

San Juan

9.8 Check Price

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.