Flights from San Jose to Chicago Starting at NZD 298

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

  • Round-trip
  • One way

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

Find the best time to fly from San Jose to Chicago

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

Cheapest flights
From price
Search
  • 16 23
  • 23 30

  • Apr

    30 6
  • 6 13
  • 13 20
  • 20 27

  • May

    27 4
  • 4 11
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

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.
Volaris Costa Rica logo Volaris Costa Rica

FAQ

  • 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 NZD 1,073.

  • How long does it take to fly from San Jose (SJO) to Chicago (CHI) and what is the distance?

    It takes around 5 hours 34 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 Intl. Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. 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.

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.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Information from San Jose to Chicago

Cheapest one-way flight price NZD 297
Cheapest round-trip ticket price NZD 801
Off-season for travel March
Peak season for travel December
Flight distance 3,568.5 km
Average flight time 5 hours 34 minutes
Popular airline Aeromexico