$107 Find Cheap Flights from San Jose to Chicago

Flights from San Jose to Chicago

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Flights from San Jose to Chicago Starting at CNY 107

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

One way
Round-trip

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?

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

Find cheap airlines flights from San Jose to Chicago

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Spirit Airlines

From $107

Frontier Airlines

From $116

United Airlines

From $144

Avianca

From $153

Jetblue Airways

From $167

American Airlines

From $214

Copa Airlines

From $224

Southwest Airlines

From $239

Aeromexico

From $262

Volaris Costa Rica

From $266

ANA airlines

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Alternative Cheap Routes from San Jose to Chicago

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from San Jose to Chicago.

Cheapest
SJO
09:36
12h 53m
1 transfer
ORD
23:29
Juan Santamaria International Airport - O'Hare International Airport
Wed, May 15Spirit Airlines
$107
SJO
09:21
11h 6m
1 transfer
MDW
21:27
Juan Santamaria International Airport - Midway International Airport
Thu, May 2Frontier Airlines
$116
SJO
14:06
27h 12m
1 transfer
RFD
18:18
Juan Santamaria International Airport - Chicago Rockford International Airport
Sun, Apr 21Jetblue Airways
$332
SJO
14:06
27h 12m
1 transfer
RFD
18:18
Juan Santamaria International Airport - Chicago Rockford International Airport
Sun, Apr 21Jetblue Airways
$332
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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 $572.
How long does it take to fly from San Jose (SJO) to Chicago (CHI) and what is the distance?
It takes around 5 hours 28 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. It takes about 40 minutes by taxi.
- The distance from Midway International Airport to downtown is about 14km. 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

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Try Different Dates

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Use the Trip.com App

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Travel Info | San Jose to Chicago

Cheapest nonstop flight price	$106
Cheapest round-trip ticket price	$316
Off-season for travel	April
Peak season for travel	July
Flight distance	3,568.5km
Average flight time	5 hours 28 minutes
Popular airline	United Airlines