Cheap Flights from San Jose to Chicago from CAD 69️ 2024

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Find San Jose to Chicago flights starting at CAD 69.

Book one-way or return flights from San Jose to Chicago from as little as CAD 69. Choose from the popular airlines below and book your flight today!

One way
Round-trip

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

Searching for the best last minute flight from San Jose to Chicago? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from San Jose to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.

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

Find Cheapest Airlines Flying from San Jose to Chicago

View airlines operating 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 CAD 69

Alaska Airlines

From CAD 125

Delta Air Lines

From CAD 130

American Airlines

From CAD 161

United Airlines

From CAD 172

Southwest Airlines

From CAD 205

ANA airlines

Find more flights and airlines

Alternative Routes for San Jose to Chicago Flights

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from San Jose to Chicago.

Cheapest
SJC
08:00
11h 55m
1 transfer
ORD
21:55
SJ International Airport - O'Hare International Airport
Wed, May 8Spirit Airlines
CAD 69
SJC
08:05
12h 0m
2 transfer
MDW
22:05
SJ International Airport - Midway International Airport
Tue, May 7Spirit Airlines
CAD 127
SJC
07:00
12h 8m
1 transfer
RFD
21:08
SJ International Airport - Chicago Rockford International Airport
Thu, May 2Spirit Airlines
CAD 312
SJC
07:00
12h 8m
1 transfer
RFD
21:08
SJ International Airport - Chicago Rockford International Airport
Thu, May 2Spirit Airlines
CAD 312
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How do I find the cheapest flights?

When are 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 are flights from San Jose (SJC) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around CAD 565.
How long is the 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 (CHI)?
There are 5 airport(s) in Chicago (CHI): Chicago Du Page County Airport, Midway International Airport, O'Hare 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

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

Compare prices on travel agency and airline websites.

Look Out for Deals

Check airline and travel agency websites for latest flight deals

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

Save up to £10 per person when booking your flights on Trip.com

Flight Information for San Jose to Chicago Flights

Cheapest direct flight price	CAD 69
Cheapest return ticket price	CAD 308
Cheapest month	May
Peak season for travel	July
Flight distance	2,958.96km
Average flight time	4 hours 42 minutes
Popular airline	Alaska Airlines