S$ 116 Cheap Flights from Chicago to San Jose (CHI-SJO)

Cheap Flights from Chicago to San Jose

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Cheap Flights from Chicago to San Jose starting at CNY 116

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 Chicago to San Jose

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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 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$ 116

Frontier Airlines

From S$ 119

Avianca

From S$ 206

American Airlines

From S$ 213

United Airlines

From S$ 265

Copa Airlines

From S$ 282

Allegiant Air

From S$ 291

Southwest Airlines

From S$ 326

Jetblue Airways

From S$ 358

Volaris

From S$ 389

ANA airlines

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Alternative Routes from Chicago to San Jose

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Chicago to San Jose.

Cheapest
ORD
18:40
17h 52m
1 transfer
SJO
11:32
O'Hare International Airport - Juan Santamaria International Airport
Sat, May 11Spirit Airlines
S$ 116
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
30h 12m
2 transfer
SJO
00:20
Chicago Rockford International Airport - Juan Santamaria International Airport
Fri, Apr 26Allegiant Air
S$ 291
RFD
19:08
30h 12m
2 transfer
SJO
00:20
Chicago Rockford International Airport - Juan Santamaria International Airport
Fri, Apr 26Allegiant Air
S$ 291
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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$ 796.
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

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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 Chicago to San Jose

Cheapest direct flight price	S$ 116
Cheapest return ticket price	S$ 446
Cheapest month	January
Peak season for travel	July
Flight distance	3,568.5km
Average flight time	5 hours 14 minutes
Popular airline	United Airlines