Find cheap one-way flights from San Jose to Chicago starting at US$172.

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

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

When is the cheapest time to book flights from San Jose to Chicago?

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

Cheapest flights

From price

16 23
23 30
Apr

30 6
6 13
13 20
20 27
May

27 4
4 11
11 18
18 25
Jun

25 1
1 8

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 $619.
How long does it take to fly from San Jose (SJO) to Chicago (CHI) and what is the distance?

It takes around 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 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.

Being flexible with your dates to get the cheapest San Jose to Chicago ticket.

Tap "Date" on flight search bar to scan through the calender for San Jose to Chicago airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Sun, Mar 23 at US$346 for one-way flights.

Compare cheap San Jose to Chicago flight deals from over hundreds of airlines.

Our extensive search allows you to compare prices from over 500 airlines to choose the cheapest flight tickets from San Jose to Chicago. The cheapest airline operating is United Airlines.

Set up a Price Alert

By setting up a Price Alert for your San Jose to Chicago route, you can easily track the price of your airline tickets from San Jose to Chicago without manually checking every day.

Don't miss cheap San Jose to Chicago flight deals and promo codes.

You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights for cheap flights. If registering a free membership, you can receive more deals for your flights.

Book early or wait unitl the last minute.

It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.

Search for flights on the go.

To get the best flight booking experience on the go, download Trip.com free app and search for cheap flight tickets from San Jose to Chicago to get exclusive deals for you.

San Jose to Chicago Flight Information

Cheapest one-way flight price	$171
Cheapest round-trip ticket price	$462
Off-season for travel	March
Peak season for travel	December
Flight distance	3,568.5 km
Average flight time	5 hours 34 minutes
Popular airline	Aeromexico