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Latest Flight Deals from Chicago to San Jose

Book one-way or return flights from Chicago to San Jose from as little as NZD 119. Choose from the popular airlines below and book your flight today!

  • One way
  • Round-trip
      • ORD05:00
        7h 32m
        1 stop
        SJO11:32
        Sat, May 11|Chicago - San Jose|Spirit Airlines
        NZD 119NZD 217
        45% OFF
        45% OFF
        NZD 217NZD 119
      • ORD17:41
        7h 23m
        1 stop
        SJO00:04
        Tue, May 14|Chicago - San Jose|Spirit Airlines
        NZD 131NZD 217
        39% OFF
        39% OFF
        NZD 217NZD 131
      • ORD17:41
        7h 23m
        1 stop
        SJO00:04
        Tue, May 21|Chicago - San Jose|Spirit Airlines
        NZD 137NZD 217
        37% OFF
        37% OFF
        NZD 217NZD 137
      • ORD17:41
        7h 23m
        1 stop
        SJO00:04
        Sat, May 18|Chicago - San Jose|Spirit Airlines
        NZD 145
        NZD 145
      • ORD10:58
        14h 6m
        1 stop
        SJO00:04
        Wed, May 15|Chicago - San Jose|Spirit Airlines
        NZD 145
        NZD 145
      • ORD17:41
        7h 23m
        1 stop
        SJO00:04
        Wed, May 8|Chicago - San Jose|Spirit Airlines
        NZD 146
        NZD 146
      • MDW17:16
        16h 30m
        1 stop
        SJO08:46
        Tue, May 7|Chicago - San Jose|Frontier Airlines
        NZD 154
        NZD 154
      • ORD10:58
        14h 6m
        1 stop
        SJO00:04
        Wed, May 22|Chicago - San Jose|Spirit Airlines
        NZD 156
        NZD 156
      • ORD17:41
        7h 23m
        1 stop
        SJO00:04
        Mon, Jun 3|Chicago - San Jose|Spirit Airlines
        NZD 161
        NZD 161
      • ORD10:58
        14h 6m
        1 stop
        SJO00:04
        Mon, May 20|Chicago - San Jose|Spirit Airlines
        NZD 161
        NZD 161
      • CHI13:00
        3h 5m
        Direct
        SJO14:00
        Tue, May 7|Chicago - San Jose|Spirit Airlines
        Find More Flights
        Find More Flights

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

Searching for the best last minute flight from Chicago to San Jose? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Chicago to San Jose. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Airlines Flying from Chicago to San Jose

View airlines operating flights from Chicago to San Jose. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Spirit Airlines
From NZD 114
Frontier Airlines
From NZD 154
American Airlines
From NZD 246
Avianca
From NZD 254
United Airlines
From NZD 326
Sun Country Airlines
From NZD 326
Porter Airlines
From NZD 425
Jetblue Airways
From NZD 442
Aeromexico
From NZD 468
Copa Airlines
From NZD 482
ANA airlines

Find more flights and airlines

Alternative Routes from Chicago to San Jose

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Chicago to San Jose.

  • Cheapest
    Spirit Airlines
    ORD
    06:10
    18h 54m
    2 transfer
    SJO
    00:04
    O'Hare International Airport - Juan Santamaria International Airport
    Tue, May 21Spirit Airlines
    NZD 114
  • Frontier Airlines
    MDW
    17:16
    16h 30m
    1 transfer
    SJO
    08:46
    Midway International Airport - Juan Santamaria International Airport
    Tue, May 7Frontier Airlines
    NZD 154
  • Allegiant Air
    RFD
    09:03
    14h 1m
    2 transfer
    SJO
    22:04
    Chicago Rockford International Airport - Juan Santamaria International Airport
    Fri, May 10Allegiant Air
    NZD 598
  • Allegiant Air
    RFD
    09:03
    14h 1m
    2 transfer
    SJO
    22:04
    Chicago Rockford International Airport - Juan Santamaria International Airport
    Fri, May 10Allegiant Air
    NZD 598
    Find More Flights

How do I find the cheapest flights?

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

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

    According to Trip.com's data, the lowest price is around NZD 989.

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

    It takes around 5 hours 14 minutes to fly from Chicago (CHI) to San Jose (SJO).

  • What is the transportation method from the main airport to downtown in San Jose?

    • The distance from Juan Santamaria International Airport to downtown is about 15km. It takes about 30 minutes by taxi.

  • What are the most popular airlines that fly from Chicago (CHI) to San Jose (SJO)?

    Airlines with flights from Chicago (CHI) to San Jose (SJO): United Airlines.

How to find a cheap flight from Chicago to San Jose

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 Chicago to San Jose. 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 Chicago to San Jose

Cheapest nonstop flight price

NZD 118

Cheapest round-trip ticket price

NZD 550

Off-season for travel

January

Peak season for travel

October

Flight distance

3,568.5km

Average flight time

5 hours 14 minutes

Popular airline

American Airlines

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