Flights from Chicago to San Jose from $339

Compare All CHI to SJC 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
AS AS · 1470	06:20 CHI 20:10 SJC	0 stop(s)	13h 50m	$339 Best	Book →

Airport Information

Key details about departure and arrival airports for this route

SJC

Norman Y. Mineta San Jose International Airport

City: San Jose
Country: US
Type: Large Airport
Elevation: 62 ft

SJC Airport Guide →

Tips for Chicago to San Jose Flights

Save money and travel smarter with these route-specific tips

📅 When to Book

Book CHI–SJC 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 $339, but prices as low as $339 are available.

✈ Direct vs Connecting

No direct flights currently listed. Consider flexible dates or nearby airports for better connections.

📍 Flexible Dates

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

Top Hotels in San Jose

Book accommodation at your destination — top-rated stays near SJC airport

Trebol Amarillo Bed & Breakfast

San Jose

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Pacuare Mountain Lodge

San Jose

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Frequently Asked Questions

Everything you need to know about flying CHI to SJC

What is the cheapest flight from Chicago to San Jose?

The cheapest flight from Chicago (CHI) to San Jose (SJC) currently starts at $339 with AS. Prices are updated regularly and may vary by date and availability.

How many airlines fly from CHI to SJC?

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

Are there direct flights from Chicago to San Jose?

No direct flights are currently listed on this route. All available options involve at least one stop. Consider flexible dates or nearby airports for better connection options.

What is the average flight price on this route?

The average flight price from Chicago to San Jose is approximately $339. Prices range from $339 to $339 depending on airline, time, and class.

How long is the flight from CHI to SJC?

The average flight duration from Chicago to San Jose is approximately 13 hours 50 minutes. Direct flights are typically shorter than connecting options.

What is the baggage allowance on CHI–SJC 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.