Find cheap flights from San Jose to Chicago starting at $201.

  • 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?

  • 612
  • 1319
  • 2026
  • Mar

    275
  • 612
  • 1319
  • 2026
  • Apr

    272
  • 39
  • 1016
  • 1723
  • 2430
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Find cheap flights from San Jose to Chicago by different airports

  • SJOMDW
    Wed, Mar 1
    One way2 transfer
    From $201
  • SJOORD
    Tue, Mar 28
    One way1 transfer
    From $215

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 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 flights from San Jose to Chicago?

    According to Trip.com's data,The cheapest flights from San Jose to Chicago found was $675.
  • How long is the flight from San Jose to Chicago?

    It takes about 5 hours 37 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): American Airlines and 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 (CHI)?

San Jose to Chicago Flight Info

Cheapest return ticket price
$325
Cheapest direct flight price
$201
Cheapest month
November
Peak season for travel
April