American – $238: San Jose, California – Chicago (and vice versa). Roundtrip, including all Taxes

There’s two valid two periods for this fare:

  • There’s a weekend fare for travel this weekend (leave after 7PM Friday or all day Saturday and return Monday or Tuesday)
  • And one from March 14th – March 25th for Monday, Tuesday and Saturday departures

Sample Travel Date:

  • March 8th – 11th

Fare Availability:

  • Valid for travel until March 25th. See above for the two different valid travel period. Must purchase by March 7th

How to Search for Availability:


  • SJC – ORD (Chicago) – DFW (Dallas) – SJC


  • 4,069 miles or 5.9 cents per mile.

How to Book:

  • Support us by using our Hotwire link to book with dates found on ITA Software Matrix Airfare Search.



For hotel bookings, we recommend that you only book using online travel agencies (, or if it is a non-chain hotel. We don’t want you to miss out on earning rewards with chain hotels.

Car Rentals

For more of the latest cheap San Francisco / Bay Area Flight Deals:

For more of the latest cheap Chicago Flight Deals:

* The Flight Deal will receive a small commission if you use the Orbitz, accommodation or car rental affiliate links to make a booking. Thank you for your continuing support.


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