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Cheap Flights From San Jose, California To Chicago, Illinois
San Jose
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Airfare Details for flights from San Jose to Chicago

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Sorry this deal is over or has been sold out! But here’s another great Airfarewatchdog verified fare for this route!

$392 RT flight from San Jose to Chicago (SJC-MDW)

  • Airline(s):
    Southwest
  • Seats are:
    Limited Availability
  • Available for travel:
    Exc Fri/Sun
  • Travel by:
    Wednesday, December 18, 2013
  • More Details:
    Includes All Taxes, No Min. Stay, Fare Can Be Bought One-way For Half The Lowest Roundtrip Price, Travel Between Aug. 26 - Dec. 18, 2013
  • Last Updated:
    Tuesday, May 21, 2013
  • Our Notes:
    Blackout Dates Apply: Nov. 26 - Dec. 3.Fare Available On Southwest.com
All mandatory taxes/fees are included in the price. Tax-inclusive fare may be a few dollars higher or lower depending on the airport you connect through, if any. Baggage fees, if applicable, and other optional fees are not included.

Our Dealhounds found this airfare using flexible date search. This means we searched a range of dates to find you the best price.

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Reviews for San Jose to Chicago (SJC-MDW)

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Sample Fares found by other travelers within the past 72 hours
Price From/To Depart/Return Airline
$558 Flight from San Jose to Midway (SJC-MDW) Wed, May 29 - Thu, Jun 6 Delta Air Lines
$673 Flight from San Jose to Midway (SJC-MDW) Thu, May 30 - Sat, Jun 1 American Airlines
$687 Flight from San Jose to Midway (SJC-MDW) Wed, May 22 - Tue, Jun 4 Delta Air Lines
$818 Flight from San Jose to Midway (SJC-MDW) Sat, May 25 - Sun, Jun 2 Delta Air Lines
$929 Flight from San Jose to Midway (SJC-MDW) Sat, May 25 - Sun, May 26 Delta Air Lines
$939 Flight from San Jose to Midway (SJC-MDW) Fri, May 24 - Sun, May 26 Delta Air Lines
$939 Flight from San Jose to Midway (SJC-MDW) Thu, May 23 - Sat, May 25 Delta Air Lines
$1,018 Flight from San Jose to Midway (SJC-MDW) Thu, May 23 - Mon, May 27 AirTran
$1,018 Flight from San Jose to Midway (SJC-MDW) Fri, May 24 - Mon, May 27 AirTran
$1,048 Flight from San Jose to Midway (SJC-MDW) Tue, May 21 - Mon, May 27 Delta Air Lines
There are approximately 38 flights covering the route from San Jose Municipal Airport in San Jose to Midway Airport in Chicago, provided by as many as 6 airlines.

The following airlines sometimes offer nonstop cheap flights from San Jose to Chicago:

Transwest Air

As an alternative to flying from San Jose, you may also want to try searching for cheap flights from Monterey (MRY).
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