S$ 107 Cheap Flights from Chicago to San Jose (CHI-SJO)

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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$ 107

Book one-way or return flights from Chicago to San Jose from as little as S$ 107. 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$ 107

Frontier Airlines

From S$ 119

American Airlines

From S$ 199

Avianca

From S$ 206

United Airlines

From S$ 265

Porter Airlines

From S$ 330

Jetblue Airways

From S$ 358

Copa Airlines

From S$ 362

Aeromexico

From S$ 379

Volaris

From S$ 389

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
Tue, May 14Spirit Airlines
S$ 107
MDW
16:51
16h 45m
1 transfer
SJO
08:36
Midway International Airport - Juan Santamaria International Airport
Sat, Apr 27Frontier Airlines
S$ 119
RFD
19:08
25h 29m
2 transfer
SJO
19:37
Chicago Rockford International Airport - Juan Santamaria International Airport
Mon, Apr 29Allegiant Air
S$ 429
RFD
19:08
25h 29m
2 transfer
SJO
19:37
Chicago Rockford International Airport - Juan Santamaria International Airport
Mon, Apr 29Allegiant Air
S$ 429
Find More Flights

Frequently Asked Questions

When to buy flight tickets from Chicago (CHI) to San Jose (SJO) 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 (SJO) cost?
According to Trip.com's data, the lowest price is around S$ 801.
How long is a flight from Chicago (CHI) to San Jose (SJO)?
It takes about 5 hours 14 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, by taxi about 30 minutes.
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.
What's the most popular airline for direct flights from Chicago (CHI) to San Jose (SJO)?
United Airlines operates 2 direct flights from Chicago (CHI) to San Jose (SJO).
How many airports in San Jose?
There are 2 airports near San Jose: Juan Santamaria International Airport and Tobias Bolanos International 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

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

Flight Information from Chicago to San Jose

Cheapest direct flight price	S$ 106
Cheapest return ticket price	S$ 446
Cheapest month	January
Peak season for travel	October
Flight distance	3,568.5km
Average flight time	5 hours 14 minutes
Popular airline	Spirit Airlines