Worldwide Coverage
Worldwide Coverage
Flights to over 5,000 cities
One-stop Service Guarantee
One-stop Service Guarantee
Price guaranteed upon confirmed payment, booking guaranteed once tickets issued
Secure Payment
Secure Payment
Convenient & reliable booking and payment system

Cheap flight deals from San Jose to Chicago Starting at IDR 4,881,666

For as little as IDR 4,881,666, you can take your next adventure to Chicago without breaking the bank. Choose between one-way and return tickets from San Jose below.

  • 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 fly from San Jose to Chicago?

These price trend charts carefully monitor and predict how flight prices from San Jose to Chicago will change. Keep a close eye on them to understand when the best time to buy your tickets is.

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

Find cheap airlines flights from San Jose to Chicago

Which airline provides the cheapest flights from San Jose to Chicago? Discover the option that best suits your travel needs before embarking on your journey.

Volaris Costa Rica
From IDR 2,499,727
Spirit Airlines
From IDR 2,545,534
avianca
From IDR 2,730,941
Volaris El Salvador
From IDR 2,730,941
Jetblue Airways
From IDR 3,171,556
Frontier Airlines
From IDR 3,278,438
United Airlines
From IDR 3,507,471
Copa Airlines
From IDR 3,815,029
Southwest Airlines
From IDR 4,065,874
Volaris
From IDR 4,196,750

Find more flights and airlines

Alternative Cheap Routes from San Jose to Chicago

Searching for potential routes that might be cheaper and faster? There are a few alternative ways to get to Chicago from San Jose which could help you save money and time.

  • Cheapest
    Volaris Costa Rica
    SJO
    05:30
    24h 55m
    2 transfer
    ORD
    06:25
    Juan Santamaria International Airport - O'Hare International Airport
    Fri, Nov 15Volaris Costa Rica
    IDR 2,499,727
  • Spirit Airlines
    SJO
    14:41
    20h 31m
    2 transfer
    MDW
    11:12
    Juan Santamaria International Airport - Midway International Airport
    Sat, Nov 16Spirit Airlines
    IDR 2,615,334
  • Spirit Airlines
    SJO
    14:41
    20h 31m
    2 transfer
    MDW
    11:12
    Juan Santamaria International Airport - Midway International Airport
    Sat, Nov 16Spirit Airlines
    IDR 2,615,334
    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 IDR 9,266,005.
  • How long does it take to fly from San Jose (SJO) to Chicago (CHI) and what is the distance?

    It takes around 5 hours 25 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 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

If you leave it until the last minute and forget to check some of the key information when booking tickets, prices can often end up skyrocketing. Below, you can find our top tips for getting the best value flights – from changing dates to chasing deals, there are plenty ways to keep your next trip affordable.
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 Info | San Jose to Chicago

Cheapest nonstop flight priceIDR 2,700,403
Cheapest round-trip ticket priceIDR 7,902,715
Off-season for travelOctober
Peak season for travelFebruary
Flight distance3,568.5 km
Average flight time5 hours 25 minutes
Popular airlineAir Canada