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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 97. Choose from the popular airlines below and book your flight today!

  • One way
  • Round-trip
      • MDW22:59
        11h 42m
        1 stop
        SJC08:41
        Tue, May 7|Chicago - San Jose|Frontier Airlines
        NZD 97NZD 208
        53% OFF
        53% OFF
        NZD 208NZD 97
      • ORD07:00
        11h 55m
        1 stop
        SJC16:55
        Wed, May 15|Chicago - San Jose|Spirit Airlines
        NZD 100NZD 208
        52% OFF
        52% OFF
        NZD 208NZD 100
      • ORD07:00
        12h
        1 stop
        SJC17:00
        Wed, Jun 5|Chicago - San Jose|Spirit Airlines
        NZD 106NZD 208
        49% OFF
        49% OFF
        NZD 208NZD 106
      • ORD21:34
        13h 7m
        1 stop
        SJC08:41
        Tue, May 7|Chicago - San Jose|Spirit Airlines
        NZD 121
        NZD 121
      • ORD07:00
        11h 55m
        1 stop
        SJC16:55
        Wed, May 8|Chicago - San Jose|Spirit Airlines
        NZD 121
        NZD 121
      • ORD14:36
        11h 19m
        1 stop
        SJC23:55
        Tue, May 14|Chicago - San Jose|Spirit Airlines
        NZD 122
        NZD 122
      • ORD19:52
        13h 23m
        1 stop
        SJC07:15
        Mon, Apr 29|Chicago - San Jose|Spirit Airlines
        NZD 142
        NZD 142
      • ORD21:34
        11h 41m
        1 stop
        SJC07:15
        Tue, Apr 30|Chicago - San Jose|Spirit Airlines
        NZD 142
        NZD 142
      • ORD19:52
        13h 23m
        1 stop
        SJC07:15
        Mon, May 6|Chicago - San Jose|Spirit Airlines
        NZD 142
        NZD 142
      • ORD22:52
        11h 49m
        1 stop
        SJC08:41
        Tue, May 21|Chicago - San Jose|Spirit Airlines
        NZD 145
        NZD 145
      • CHI13:00
        3h 5m
        Direct
        SJC14:00
        Sun, May 5|Chicago - San Jose|Frontier 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.

Frontier Airlines
From NZD 97
Spirit Airlines
From NZD 121
Alaska Airlines
From NZD 158
Delta Air Lines
From NZD 170
American Airlines
From NZD 216
United Airlines
From NZD 221
Southwest Airlines
From NZD 256
Sun Country Airlines
From NZD 309
Allegiant Air
From NZD 385
Jetblue Airways
From NZD 521
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
    Frontier Airlines
    MDW
    22:59
    11h 42m
    1 transfer
    SJC
    08:41
    Midway International Airport - SJ International Airport
    Tue, May 7Frontier Airlines
    NZD 97
  • Spirit Airlines
    ORD
    07:00
    11h 55m
    1 transfer
    SJC
    16:55
    O'Hare International Airport - SJ International Airport
    Wed, May 8Spirit Airlines
    NZD 121
  • Allegiant Air
    RFD
    21:30
    13h 44m
    1 transfer
    SJC
    09:14
    Chicago Rockford International Airport - SJ International Airport
    Fri, May 24Allegiant Air
    NZD 385
  • Allegiant Air
    RFD
    21:30
    13h 44m
    1 transfer
    SJC
    09:14
    Chicago Rockford International Airport - SJ International Airport
    Fri, May 24Allegiant Air
    NZD 385
    Find More Flights

How do I find the cheapest flights?

  • When are flight tickets from Chicago (CHI) to San Jose (SJC) 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 (SJC) cost?

    According to Trip.com's data, the lowest price is around NZD 680.

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

    It takes around 7 hours 13 minutes to fly from Chicago (CHI) to San Jose (SJC).

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

    • The distance from SJ International Airport to downtown is about 4km. It takes about 20 minutes by taxi.

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

    Airlines with flights from Chicago (CHI) to San Jose (SJC): Southwest Airlines and 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 97

Cheapest round-trip ticket price

NZD 421

Off-season for travel

December

Peak season for travel

October

Flight distance

2,958.96km

Average flight time

7 hours 13 minutes

Popular airline

American Airlines

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