Alitalia – $699: San Francisco / Chicago – Milan, Italy. Roundtrip, including all Taxes

This is basically the same price as going from New York — as in, this is a good deal! If you want Medallion Qualifying Dollars, Delta has this for $778.

There’s not a lot of availability. Do not dwell on this — Orbitz lets you cancel risk free until 11PM next day.

Update 5/12/2014 @ 10:25PM – also available from Chicago.

Update 5/13/2014 @ 4:50AM – deal gone

Piazza del Duomo - Milan, Italy - Photo: Foto di Spalle, used under Creative Commons License (By 2.0)

Piazza del Duomo – Milan, Italy – Photo: Foto di Spalle, used under Creative Commons License (By 2.0)

Sample Travel Date:

  • Sample from San Francisco
  • September 17th – 24th

Fare Availability:

  • Valid for travel on the outbound from September 10th – October 28th for Sunday through Wednesday departures from the United States and Monday through Thursday departures to the United States. Must purchase by May 13th

How to Search for Availability:

Fare Class:

  • O


  • SFO – JFK (New York) – FCO (Rome) – MXP (Milan) – JFK – SFO



  • 13,744 miles or 5.0 cents per mile. Alitalia is a member of the SkyTeam alliance and Delta partner. This fare will earn 100% mileage with Delta

How to Book:

  • Support us by using our Orbitz link to book with dates found on ITA Software Matrix Airfare Search. Make sure to select “Additional Search Options” and then “Narrow the search to my preferred airlines” and select Alitalia
  • Save $400 off your next travel purchase after signing up for the Barclaycard Arrival Plus™ World Elite MasterCard®.* Earn 40,000 bonus miles when you spend $3,000 on purchases in the first 90 days – that’s enough to redeem for a $400 travel statement credit



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

Background Information:

  • Visa: US Citizens – not required. Other nationals, check the TIMATIC Visa Database
  • Currency: Euro (EUR). $1USD = 0.73 EUR

Tips for saving when using credit cards at international destinations:

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 commission if you use the Orbitz, accommodation or car rental affiliate links to make a booking or apply and is approved for a credit card using our link above. Thank you for your continuing support.


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The Flight Deal does not sell travel products or services. We provide you with information about third-party travel suppliers’ offers, and link you to their sites. The information posted by The Flight Deal is valid at the time of publication. However, we have no control over the suppliers, and we therefore do not warrant or guarantee that their offers will not change or become unavailable. Nor are we responsible for their products, services or site content. Please see their sites for their most up-to-date offer information and all applicable terms and conditions.

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