Cheap Flights from San Jose to Chicago starting at € 163

We've found these cheap flights for you. You can book one-way or return flight tickets.

Round-trip
One way

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Cheapest time to fly from San Jose to Chicago

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Cheapest flights

From price

2 9
9 16
16 23
23 30
Apr

30 6
6 13
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20 27
May

27 4
4 11
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18 25

Displayed prices are calculated based on the lowest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

When to buy flight tickets from San Jose (SJO) to Chicago (CHI) the cheapest?

Airlines adjust prices for flights from San Jose to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much is a flight from San Jose (SJO) to Chicago (CHI) cost?

According to Trip.com's data, the lowest price is around € 555.
How long is a flight from San Jose (SJO) to Chicago (CHI)?

It takes about 5 hours 34 minutes to fly from San Jose (SJO) to Chicago (CHI).
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
- The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
What time does the earliest flight from San Jose to Chicago depart?

The earliest flight departs from San Jose (SJO) at 06:05 and arrives in Chicago (ORD) at 12:35.
What are the most popular airlines that fly from San Jose (SJO) to Chicago (CHI)?

Airlines with flights from San Jose (SJO) to Chicago (CHI): United Airlines.
What's the most popular airline for direct flights from San Jose (SJO) to Chicago (CHI)?

American Airlines operates 2 direct flights from San Jose (SJO) to Chicago (CHI).
How many airports in Chicago?

There are 3 airports near Chicago: O'Hare International Airport, Midway International Airport and Chicago Rockford International Airport.

How to find a cheap flight from San Jose to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from San Jose to Chicago. Book your flights at the right time and save more.

Book Early

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Compare Flight Prices

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Check One-way Fares

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Find cheapest flight ticket from San Jose to Chicago

Cheapest direct flight price	€ 162
Cheapest return ticket price	€ 435
Off-season for travel	March
Peak season for travel	January
Flight distance	3,568.5km
Average flight time	5 hours 34 minutes
Popular airline	Aeromexico