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Cheap Flights from San Jose to Chicago starting at S$ 173

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

We monitor flight fares to help you find the best deals effortlessly

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$ 173
Frontier Airlines
From S$ 179
United Airlines
From S$ 215
Jetblue Airways
From S$ 226
Avianca
From S$ 246
Copa Airlines
From S$ 302
Aeromexico
From S$ 319
Southwest Airlines
From S$ 324
Volaris Costa Rica
From S$ 360
American Airlines
From S$ 420
ANA airlines

Find more flights and airlines

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
    Spirit Airlines
    SJO
    00:51
    7h 47m
    1 transfer
    ORD
    09:38
    Juan Santamaria International Airport - O'Hare International Airport
    Tue, Apr 23Spirit Airlines
    S$ 173
  • Frontier Airlines
    SJO
    09:21
    11h 11m
    1 transfer
    MDW
    21:32
    Juan Santamaria International Airport - Midway International Airport
    Thu, Apr 11Frontier Airlines
    S$ 179
  • Jetblue Airways
    SJO
    14:06
    27h 12m
    1 transfer
    RFD
    18:18
    Juan Santamaria International Airport - Chicago Rockford International Airport
    Sun, Apr 21Jetblue Airways
    S$ 449
  • Jetblue Airways
    SJO
    14:06
    27h 12m
    1 transfer
    RFD
    18:18
    Juan Santamaria International Airport - Chicago Rockford International Airport
    Sun, Apr 21Jetblue Airways
    S$ 449
    Find More Flights

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$ 938.
  • How long is a flight from San Jose (SJO) to Chicago (CHI)?

    It takes about 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, 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?

Find cheapest flight ticket from San Jose to Chicago

Cheapest direct flight price

S$ 172

Cheapest return ticket price

S$ 427

Cheapest month

January

Peak season for travel

September