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Find cheap one-way flights from San Jose to Chicago starting at US$128.

We've found these cheap flights for you. You can book one-way or round-trip flight tickets.

  • One way
  • Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to book flights from San Jose to Chicago?

We monitor flight fares to help you find 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 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 US$128
Frontier Airlines
From US$129
United Airlines
From US$159
Jetblue Airways
From US$167
Avianca
From US$182
Copa Airlines
From US$224
Aeromexico
From US$236
Southwest Airlines
From US$240
Volaris Costa Rica
From US$267
American Airlines
From US$311
ANA airlines

Find more flights and airlines

Find cheap flights from San Jose to Chicago by different airports

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

  • Cheapest
    Spirit Airlines
    SJO
    00:51
    7h 47m
    1 transfer
    ORD
    09:38
    Juan Santamaria International Airport - O'Hare International Airport
    Tue, Apr 23Spirit Airlines
    US$128
  • Frontier Airlines
    SJO
    23:50
    13h 25m
    1 transfer
    MDW
    14:15
    Juan Santamaria International Airport - Midway International Airport
    Mon, Apr 8Frontier Airlines
    US$129
  • Jetblue Airways
    SJO
    14:06
    27h 12m
    1 transfer
    RFD
    18:18
    Juan Santamaria International Airport - Chicago Rockford International Airport
    Sun, Apr 21Jetblue Airways
    US$332
  • Jetblue Airways
    SJO
    14:06
    27h 12m
    1 transfer
    RFD
    18:18
    Juan Santamaria International Airport - Chicago Rockford International Airport
    Sun, Apr 21Jetblue Airways
    US$332
    Find More Flights

Frequently Asked Questions

  • When are flight tickets from San Jose (SJO) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from San Jose to Chicago 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 San Jose (SJO) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around $695.
  • How long does it take to fly from San Jose (SJO) to Chicago (CHI) and what is the distance?

    It takes around 5 hours 26 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. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14km. It takes about 30 minutes by taxi.
  • 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.

San Jose to Chicago Flight Information

Cheapest nonstop flight price

$127

Cheapest round-trip ticket price

$316

Off-season for travel

January

Peak season for travel

September