Beginning of main content

Cheap Flights from Chicago to San Jose from $304

Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search over 1,000,000 properties worldwide and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheap MDW to SJC Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Aug 31 - Sun, Sep 8
MDW
Chicago
to
SJC
San Jose
$304

roundtrip

found 2 days ago

Open MDW to SJC flights search result page
Fri, Sep 20 - Wed, Sep 25
MDW
Chicago
to
SJC
San Jose
$309

roundtrip

found 20 hours ago

Open MDW to SJC flights search result page
Tue, Oct 1 - Mon, Oct 7
MDW
Chicago
to
SJC
San Jose
$317

roundtrip

found 2 days ago

Open MDW to SJC flights search result page
Sat, Aug 10 - Fri, Aug 16
MDW
Chicago
to
SJC
San Jose
$318

roundtrip

found 4 days ago

Open MDW to SJC flights search result page
Fri, Sep 6 - Sun, Sep 15
MDW
Chicago
to
SJC
San Jose
$319

roundtrip

found 1 day ago

Open MDW to SJC flights search result page
Fri, Aug 9 - Sat, Aug 17
MDW
Chicago
to
SJC
San Jose
$322

roundtrip

found 1 day ago

Open MDW to SJC flights search result page
Tue, Sep 3 - Tue, Sep 10
MDW
Chicago
to
SJC
San Jose
$324

roundtrip

found 16 hours ago

Open MDW to SJC flights search result page
Tue, Sep 3 - Tue, Sep 10
MDW
Chicago
to
SJC
San Jose
$327

roundtrip

found 16 hours ago

Open MDW to SJC flights search result page
Tue, Sep 3 - Tue, Sep 10
MDW
Chicago
to
SJC
San Jose
$330

roundtrip

found 16 hours ago

Open MDW to SJC flights search result page
Thu, Sep 5 - Sat, Sep 14
MDW
Chicago
to
SJC
San Jose
$335

roundtrip

found 1 day ago

Open MDW to SJC flights search result page
Tue, Sep 3 - Tue, Sep 10
MDW
Chicago
to
SJC
San Jose
$335

roundtrip

found 16 hours ago

Open MDW to SJC flights search result page
Wed, Aug 7 - Sun, Aug 11
MDW
Chicago
to
SJC
San Jose
$336

roundtrip

found 4 days ago

Open MDW to SJC flights search result page
Tue, Oct 1 - Mon, Oct 7
MDW
Chicago
to
SJC
San Jose
$339

roundtrip

found 2 days ago

Open MDW to SJC flights search result page
Fri, Sep 20 - Wed, Sep 25
MDW
Chicago
to
SJC
San Jose
$340

roundtrip

found 20 hours ago

Open MDW to SJC flights search result page
Fri, Sep 20 - Wed, Sep 25
MDW
Chicago
to
SJC
San Jose
$341

roundtrip

found 20 hours ago

Open MDW to SJC flights search result page
Thu, Mar 5 - Tue, Mar 10
MDW
Chicago
to
SJC
San Jose
$342

roundtrip

found 1 day ago

Open MDW to SJC flights search result page
Fri, Sep 20 - Wed, Sep 25
MDW
Chicago
to
SJC
San Jose
$343

roundtrip

found 20 hours ago

Open MDW to SJC flights search result page
Tue, Jul 9 - Tue, Jul 16
MDW
Chicago
to
SJC
San Jose
$344

roundtrip

found 6 days ago

Open MDW to SJC flights search result page

Chicago to San Jose route information

Origin Airport Midway Intl.
Destination Airport Norman Y. Mineta San Jose Intl.
Airlines Serving Delta
Flight Price $304
Distance 1,833 mi

Chicago

ORD-O'Hare Intl.

$236.18

San Francisco

SFO-San Francisco Intl.

$291.26

Oakland

OAK-Oakland Intl.

$343.20

Top Routes from Chicago

Top Routes to San Jose

Cheap MDW to SJC Flights

  • Question : How long is the flight from MDW to SJC?
    Answer : Southwest Airlines can get you there in four hours and 40 minutes. So, if you were to leave Chicago at 8:50 AM CDT, you would arrive in San Jose at 11:30 AM PDT. Just enough time to catch up on your sleep before you land (don't forget, there is a two-hour time difference).
  • Question : What airports do you fly into for San Jose?
    Answer : Chicago Midway International Airport is a wonderful airport, but there are lower cost ways to get to San Jose— O'Hare International Airport. It's only 16 miles away and flights are being priced 27% cheaper over the next two months.
  • Question : How much is a plane ticket to San Jose (SJC) from Chicago (MDW)?
    Answer : Cost can range from $318 to $1,032, prices for MDW to SJC change less than most routes in the United States. Prices tend to be lower the further out you book.
  • Question : How long does the average person stay in San Jose?
    Answer : Of course, you're not an average person, but if you were, you'd stay around 10 days.
  • Question : From Chicago to San Jose, which day is going to have the most flight times?
    Answer : Saturday has the greatest variety of flight times for Chicago to San Jose with three. Note that the day with the most flight times from the United States is Sunday with 8,106.
  • Question : How many flights are there per day from Chicago to San Jose?
    Answer : Depending on the day, the number of flight times will change, but on average there are three. That is lower than the national average of nine.
  • Question : What is the cheapest airline flying from Chicago to San Jose?
    Answer : Delta Air Lines is offering the best deal at $318. Better reserve fast because prices range all the way up to $1,032 over the next three months.