S$ 145 Cheap Flights from San Jose to Chicago (SJO-CHI)

Cheap Flights from San Jose to Chicago

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Cheap Flights from San Jose to Chicago starting at CNY 145

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 San Jose to Chicago

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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 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 S$ 145

Frontier Airlines

From S$ 165

Avianca

From S$ 209

United Airlines

From S$ 216

Jetblue Airways

From S$ 227

Copa Airlines

From S$ 304

American Airlines

From S$ 306

Southwest Airlines

From S$ 325

Aeromexico

From S$ 356

Volaris Costa Rica

From S$ 362

ANA airlines

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Alternative Routes from San Jose to Chicago

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

Cheapest
SJO
09:36
12h 53m
1 transfer
ORD
23:29
Juan Santamaria International Airport - O'Hare International Airport
Wed, May 15Spirit Airlines
S$ 145
SJO
09:36
12h 20m
1 transfer
MDW
22:56
Juan Santamaria International Airport - Midway International Airport
Sat, Apr 27Spirit Airlines
S$ 158
SJO
14:06
27h 12m
1 transfer
RFD
18:18
Juan Santamaria International Airport - Chicago Rockford International Airport
Sun, Apr 21Jetblue Airways
S$ 451
SJO
14:06
27h 12m
1 transfer
RFD
18:18
Juan Santamaria International Airport - Chicago Rockford International Airport
Sun, Apr 21Jetblue Airways
S$ 451
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Frequently Asked Questions

When to buy flight tickets from San Jose (SJO) 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 is a flight from San Jose (SJO) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around S$ 778.
How long is a flight from San Jose (SJO) to Chicago (CHI)?
It takes about 5 hours 28 minutes to fly from San Jose (SJO) 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 time does the earliest flight from San Jose to Chicago depart?
The earliest flight departs from San Jose (SJO) at 06:05 and arrives in Chicago (ORD) at 12:35.
What are the most popular airlines that fly from San Jose (SJO) to Chicago (CHI)?
Airlines with flights from San Jose (SJO) to Chicago (CHI): United Airlines.
What's the most popular airline for direct flights from San Jose (SJO) to Chicago (CHI)?
American Airlines operates 2 direct flights from San Jose (SJO) to Chicago (CHI).
How many airports in Chicago?
There are 5 airports near Chicago: O'Hare International Airport, Chicago Du Page County Airport, Midway 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

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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 San Jose to Chicago

Cheapest direct flight price	S$ 145
Cheapest return ticket price	S$ 430
Cheapest month	April
Peak season for travel	July
Flight distance	3,568.5km
Average flight time	5 hours 28 minutes
Popular airline	United Airlines