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Find Chicago to San Jose flights starting at CAD 53.

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.

Chicago to San Jose flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule
  1. F91596

    06:00

    ORD

    2.1h

    09:08

    ATL

    S-T-TF-
  2. F93215

    20:00

    ATL

    4.6h

    21:35

    LAX

    SMTWTFS
  3. F94081

    10:40

    LAX

    1.3h

    12:00

    SJC

    S--WT-S
  4. F92209

    06:15

    MDW

    2.8h

    08:01

    DEN

    SMTWTFS
  5. F91993

    09:59

    DEN

    2.1h

    11:05

    LAS

    SM-WTFS
  6. F94103

    15:33

    LAS

    1.4h

    17:00

    SJC

    S--WT-S
  7. F92209

    06:15

    MDW

    2.8h

    08:01

    DEN

    SMTWTFS
  8. F94917

    13:20

    DEN

    2.7h

    15:03

    SJC

    S-T-T--
  9. F92329

    06:25

    MDW

    4.0h

    08:24

    LAS

    S--WTFS
  10. F94103

    15:33

    LAS

    1.4h

    17:00

    SJC

    S--WT-S
  11. F93173

    07:50

    ORD

    2.8h

    09:40

    DEN

    SMTWTF-
  12. F92015

    07:00

    DEN

    2.0h

    08:03

    LAS

    S-TWTFS
  13. F94103

    15:33

    LAS

    1.4h

    17:00

    SJC

    S--WT-S
  14. F93173

    07:50

    ORD

    2.8h

    09:40

    DEN

    SMTWTF-
  15. F91993

    09:59

    DEN

    2.1h

    11:05

    LAS

    SM-WTFS
  16. F94103

    15:33

    LAS

    1.4h

    17:00

    SJC

    S--WT-S
  17. F93173

    07:50

    ORD

    2.8h

    09:40

    DEN

    SMTWTF-
  18. F94917

    13:20

    DEN

    2.7h

    15:03

    SJC

    S-T-T--
  19. F91827

    13:54

    ORD

    4.2h

    16:04

    PHX

    SMTWTFS
  20. F94291

    09:45

    PHX

    2.0h

    10:44

    SJC

    S--WT-S
  21. F92145

    19:59

    ORD

    4.2h

    22:11

    LAS

    S--WTFS
  22. F94103

    15:33

    LAS

    1.4h

    17:00

    SJC

    S--WT-S

When is the cheapest time to fly from Chicago to San Jose?

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

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

FAQ

  • 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 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 are flights from Chicago (CHI) to San Jose (SJC) cost?

    According to Trip.com's data, the lowest price is around CAD 420.
  • How long is the flight from Chicago (CHI) to San Jose (SJC)?

    It takes about 6 hours 50 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, by taxi about 20 minutes.
  • 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.
  • What's the most popular airline for direct flights from Chicago (CHI) to San Jose (SJC)?

    United Airlines operates 4 direct flights from Chicago (CHI) to San Jose (SJC).
  • How many airports in San Jose (SJC)?

    There are 1 airport(s) in San Jose (SJC): SJ International Airport.

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 for Chicago to San Jose Flights

Cheapest direct flight priceCAD 52
Cheapest return ticket priceCAD 250
Off-season travel monthMarch
Peak season for travelNovember
Flight distance2,958.96km
Average flight time6 hours 50 minutes
Popular airlineAlaska Airlines