S$ 74 Cheap Flights from Chicago to San Jose (CHI-SJC)

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Cheap Flights from Chicago to San Jose

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Cheap Flights from Chicago to San Jose starting at S$ 74

Book one-way or return flights from Chicago to San Jose from as little as S$ 74. 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 Chicago to San Jose? Find one-way or return flights that are affordable and fit your itinerary.

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

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

Cheapest Airlines flying from Chicago to San Jose

View airlines operating flights from Chicago to San Jose. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Spirit Airlines

From S$ 74

Frontier Airlines

From S$ 94

American Airlines

From S$ 169

Alaska Airlines

From S$ 174

Delta Air Lines

From S$ 200

Southwest Airlines

From S$ 207

United Airlines

From S$ 209

Sun Country Airlines

From S$ 292

Allegiant Air

From S$ 311

Jetblue Airways

From S$ 546

ANA airlines

Find more flights and airlines

Alternative Routes from Chicago to San Jose

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

Cheapest
ORD
22:52
11h 49m
1 transfer
SJC
08:41
O'Hare International Airport - SJ International Airport
Tue, May 21Spirit Airlines
S$ 74
MDW
21:10
13h 14m
1 transfer
SJC
08:24
Midway International Airport - SJ International Airport
Tue, Jun 4Frontier Airlines
S$ 94
RFD
21:30
13h 44m
1 transfer
SJC
09:14
Chicago Rockford International Airport - SJ International Airport
Fri, May 24Allegiant Air
S$ 311
RFD
21:30
13h 44m
1 transfer
SJC
09:14
Chicago Rockford International Airport - SJ International Airport
Fri, May 24Allegiant Air
S$ 311
Find More Flights

Frequently Asked Questions

When to buy flight tickets from Chicago (CHI) to San Jose (SJC) the cheapest?
Airlines adjust prices for flights from Chicago to San Jose 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 Chicago (CHI) to San Jose (SJC) cost?
According to Trip.com's data, the lowest price is around S$ 559.
How long is a flight from Chicago (CHI) to San Jose (SJC)?
It takes about 7 hours 14 minutes to fly from Chicago (CHI) to San Jose (SJC).
What is the transportation method from the main airport to downtown in San Jose?
- The distance from SJ International Airport to downtown is about 4km, by taxi about 20 minutes.
What time does the earliest flight from Chicago to San Jose depart?
The earliest flight departs from Chicago (MDW) at 08:00 and arrives in San Jose (SJC) at 10:25.
What time does the latest flight from Chicago to San Jose depart?
The latest flight departs from Chicago (ORD) at 19:54 and arrives in San Jose (SJC) at 22:45.
What are the most popular airlines that fly from Chicago (CHI) to San Jose (SJC)?
Airlines with flights from Chicago (CHI) to San Jose (SJC): Southwest Airlines and United Airlines.
What's the most popular airline for direct flights from Chicago (CHI) to San Jose (SJC)?
United Airlines operates 4 direct flights from Chicago (CHI) to San Jose (SJC).
How many airports in San Jose?
There are 2 airports near San Jose: SJ International Airport and San Jose Reid-Hillview Airport.

How to find a cheap flight from Chicago to San Jose

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 Chicago to San Jose. 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

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Flight Information from Chicago to San Jose

Cheapest direct flight price	S$ 74
Cheapest return ticket price	S$ 402
Cheapest month	May
Peak season for travel	July
Flight distance	2,958.96km
Average flight time	7 hours 14 minutes
Popular airline	American Airlines