S$ 89 Cheap Flights from San Jose to Chicago (SJC-CHI)

Cheap Flights from San Jose to Chicago

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Cheap Flights from San Jose to Chicago starting at CNY 89

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

One way
Round-trip

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

Cheapest Airlines flying 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 S$ 89

Alaska Airlines

From S$ 123

Delta Air Lines

From S$ 128

Southwest Airlines

From S$ 146

American Airlines

From S$ 166

United Airlines

From S$ 166

Jetblue Airways

From S$ 462

ANA airlines

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Alternative 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
SJC
09:53
7h 3m
1 transfer
ORD
18:56
SJ International Airport - O'Hare International Airport
Wed, May 8Spirit Airlines
S$ 89
SJC
09:15
24h 21m
1 transfer
MDW
11:36
SJ International Airport - Midway International Airport
Tue, Apr 23Spirit Airlines
S$ 122
SJC
08:05
10h 51m
1 transfer
RFD
20:56
SJ International Airport - Chicago Rockford International Airport
Sun, Apr 21Spirit Airlines
S$ 334
SJC
08:05
10h 51m
1 transfer
RFD
20:56
SJ International Airport - Chicago Rockford International Airport
Sun, Apr 21Spirit Airlines
S$ 334
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Frequently Asked Questions

When to buy flight tickets from San Jose (SJC) 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 (SJC) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around S$ 541.
How long is a flight from San Jose (SJC) to Chicago (CHI)?
It takes about 4 hours 42 minutes to fly from San Jose (SJC) 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 are the most popular airlines that fly from San Jose (SJC) to Chicago (CHI)?
Airlines with flights from San Jose (SJC) to Chicago (CHI): Southwest Airlines and United Airlines.
What's the most popular airline for direct flights from San Jose (SJC) to Chicago (CHI)?
United Airlines operates 2 direct flights from San Jose (SJC) to Chicago (CHI).
How many airports in Chicago?
There are 5 airports near Chicago: O'Hare International Airport, Chicago Du Page County Airport, Midway International Airport, Chicago Palwaukee 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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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

Flying during the week, early in the morning, or late at night can help save money.

Use the Trip.com App

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Find cheapest flight ticket from San Jose to Chicago

Cheapest direct flight price	S$ 88
Cheapest return ticket price	S$ 305
Cheapest month	February
Peak season for travel	July
Flight distance	2,958.96km
Average flight time	4 hours 42 minutes
Popular airline	Alaska Airlines