Flights from San Juan to Chicago from $269

SJU

San Juan

One-way

CHI

Chicago

Flights from

$269

Compare 1 options across 1 airline

Updated 1 month ago

$269

Cheapest Flight

$269

Average Price

Direct Flights

Airlines

Looking for the return flight? Chicago to San Juan from $185

CHI → SJU Flights

Compare All SJU to CHI Flights

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

1 of 1 flight

Airline	Schedule	Stops	Duration	Price
F9 F9 · 3345	Schedule on partner site	Direct	—	$269 Best	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 San Juan to Chicago Flights

Save money and travel smarter with these route-specific tips

📅 When to Book

Book SJU–CHI 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 $269, but prices as low as $269 are available.

✈ Direct vs Connecting

1 direct flight(s) available on this route . Direct flights save you 2–5 hours of travel time.

📍 Flexible Dates

Flying midweek (Tuesday–Thursday) on SJU–CHI is typically 15–30% cheaper. Use our price comparison to spot the best day to fly.

Frequently Asked Questions

Everything you need to know about flying SJU to CHI

What is the cheapest flight from San Juan to Chicago?

The cheapest flight from San Juan (SJU) to Chicago (CHI) currently starts at $269 with F9. Prices are updated regularly and may vary by date and availability.

How many airlines fly from SJU to CHI?

We found 1 airline(s) operating on the SJU–CHI route, including F9.

Are there direct flights from San Juan to Chicago?

Yes, there are 1 direct flight(s) available from SJU to CHI, with prices starting at $269.

What is the average flight price on this route?

The average flight price from San Juan to Chicago is approximately $269. Prices range from $269 to $269 depending on airline, time, and class.

What is the baggage allowance on SJU–CHI 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 $269

Book Cheapest →