US$75️ Cheap Flights from Chicago to San Jose (2024)

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Chicago to San Jose - Flights Starting at US$75

Book one-way or return flights from Chicago to San Jose from as little as US$75. 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.

We've found these cheap flights for you. You may book a one-way or round trip as per your needs.

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

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

Cheapest airlines flights 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 US$75

Frontier Airlines

From US$96

American Airlines

From US$147

Avianca

From US$152

United Airlines

From US$195

Copa Airlines

From US$238

Porter Airlines

From US$254

Jetblue Airways

From US$264

Sun Country Airlines

From US$272

Aeromexico

From US$279

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
17:41
7h 23m
1 transfer
SJO
00:04
O'Hare International Airport - Juan Santamaria International Airport
Wed, May 29Spirit Airlines
US$75
MDW
17:16
16h 30m
1 transfer
SJO
08:46
Midway International Airport - Juan Santamaria International Airport
Tue, May 14Frontier Airlines
US$96
MDW
17:16
16h 30m
1 transfer
SJO
08:46
Midway International Airport - Juan Santamaria International Airport
Tue, May 14Frontier Airlines
US$96
Find More Flights

Frequently Asked Questions

When are flight tickets from Chicago (CHI) to San Jose (SJO) the cheapest?
Airlines adjust prices for flights from Chicago to San Jose 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 Chicago (CHI) to San Jose (SJO) cost?
According to Trip.com's data, the lowest price is around $599.
How long does it take to fly from Chicago (CHI) to San Jose (SJO) and what is the distance?
It takes around 5 hours 21 minutes to fly from Chicago (CHI) to San Jose (SJO).
What is the transportation method from the main airport to downtown in San Jose?
- The distance from Juan Santamaria International Airport to downtown is about 15km. It takes about 30 minutes by taxi.
What are the most popular airlines that fly from Chicago (CHI) to San Jose (SJO)?
Airlines with flights from Chicago (CHI) to San Jose (SJO): United Airlines.

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

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

Chicago to San Jose Flight Information

Cheapest nonstop flight price	$74
Cheapest round-trip ticket price	$328
Off-season for travel	May
Peak season for travel	August
Flight distance	3,568.5km
Average flight time	5 hours 21 minutes
Popular airline	American Airlines