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Cheap Flights From San Jose, California (SJC) To Chicago, Illinois (MDW)

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Fares from San Jose, CA (SJC)
$278 RT to
Chicago, IL (MDW)
Sorry this deal is over or has been sold out! But here’s another great Airfarewatchdog verified fare for this route!
$278 RT San Jose to Chicago, IL
Airline(s)
Southwest
Seats:
Seats are not available on all flights or all dates of travel. You may need to have flexible travel dates to find this fare. Fares for travel on holidays may be higher.
Adv. Purchase:
21 Days
Travel Ending:
Friday, 31 October 2014
More Details:
Non-Stop Flights, No min. stay, Fare can be bought one-way for half the lowest roundtrip price, No peak summer travel at this price
Last Updated:
Wednesday, 23 April 2014
Our Notes:
This is a fare from Southwest. Visit Southwest.com to find this fare. Other airlines often match Southwest sales, so search other sites to find your best option.
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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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"Might Try Again" 04/22/2014
"Great weekend!!!" 04/22/2014
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"Amazing hotel and excellent staff!" 04/22/2014
"Perfect - AGAIN !!!" 04/21/2014
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"A Home Run of a Weekend" 03/11/2014
"Excellent service, great value" 03/07/2014

More Flights From San Jose To Chicago (SJC-MDW)

Price
Details
$364 RT No min. stay. Fare can be bought one-way for half the lowest roundtrip ... (Southwest) See all details »
  • Airline(s):
    Southwest
  • Seats are:
    Seats Are Not Available On All Flights Or All Dates Of Travel. You May Need To Have Flexible Travel Dates To Find This Fare. Fares For Travel On Holidays May Be Higher.
  • Advance Purchase:
    14 Days
  • Available for travel:
    Mon-Thur & Sat
  • Travel ending:
    Thursday, October 30, 2014
  • More Details:
    No min. stay, Fare can be bought one-way for half the lowest roundtrip price, No peak summer travel at this price, No peak spring break/summer travel at ...morethis price
  • Last Updated:
    Tuesday, April 22, 2014
  • Our Notes:
    Travel May 6 through June 7 or August 25 through October 30, 2014, excluding Fridays and Sundays. Travel to Florida or Nevada is valid Sunday through Wednesday ...moreonly. Additionally, travel from Florida or Nevada valid Tuesday through Friday only. Travel between Nevada and Florida is valid on Tuesdays and Wednesdays only. This is a fare from Southwest - visit Southwest.com to find this fare. Other airlines often match Southwest sales, so search other sites to find the best option.

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
$332 Flight from San Jose to Midway (SJC-MDW) Tue, May 6 - Wed, May 7 Delta Air Lines
$342 Flight from San Jose to Midway (SJC-MDW) Sat, May 31 - Tue, Jun 3 Delta Air Lines
$457 Flight from San Jose to Midway (SJC-MDW) Fri, May 2 - Thu, May 8 Delta Air Lines
$491 Flight from San Jose to Midway (SJC-MDW) Thu, Jun 5 - Tue, Jun 10 Delta Air Lines
$545 Flight from San Jose to Midway (SJC-MDW) Wed, Jun 4 - Sun, Jun 8 Delta Air Lines
$632 Flight from San Jose to Midway (SJC-MDW) Thu, Jul 24 - Tue, Jul 29 Delta Air Lines
$640 Flight from San Jose to Midway (SJC-MDW) Thu, May 8 - Mon, May 12 Delta Air Lines
$640 Flight from San Jose to Midway (SJC-MDW) Thu, Jul 31 - Mon, Aug 4 Delta Air Lines
$671 Flight from San Jose to Midway (SJC-MDW) Thu, Jul 31 - Tue, Aug 5 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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