Cheap flight deals from San Jose to Chicago Starting at $171

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

Round-trip
One way

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

When is the cheapest time to fly from San Jose to Chicago?

We monitor flight fares to help you find the best deals effortlessly

Cheapest flights

From price

2 9
9 16
16 23
23 30
Apr

30 6
6 13
13 20
20 27
May

27 4
4 11
11 18
18 25

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

Frequently Asked Questions

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

Airlines adjust prices for flights from San Jose to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much do flights from San Jose (SJO) to Chicago (CHI) cost?

According to Trip.com's data, the lowest price is around $586.
How long does it take to fly from San Jose (SJO) to Chicago (CHI) and what is the distance?

It takes around 5 hours 25 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 Intl. Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
- The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.
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.

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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Look Out for Deals

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Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

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Flight Info | San Jose to Chicago

Cheapest nonstop flight price	$171
Cheapest round-trip ticket price	$456
Off-season for travel	March
Peak season for travel	June
Flight distance	3,568.5 km
Average flight time	5 hours 25 minutes
Popular airline	Aeromexico