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Roundtrip flights from San Jose to Honolulu starting at $270


Roundtrip flights from San Jose to Tokyo starting at $569


Roundtrip flights from San Jose to Guadalaj... starting at $222


Roundtrip flights from San Jose to Kahului starting at $271


Roundtrip flights from San Jose to New York starting at $234


Roundtrip flights from San Jose to Seattle starting at $118


Roundtrip flights from San Jose to Cancun starting at $398


Roundtrip flights from San Jose to Los Ange... starting at $91


Roundtrip flights from San Jose to Los Cabo... starting at $278


Roundtrip flights from San Jose to San Dieg... starting at $82


San Jose to Chicago route information

Origin Airport Norman Y. Mineta San Jose Intl.
Destination Airport Midway Intl.
Airlines Serving Delta
Flight Price $308
Distance 1,833 mi

San Francisco

$288.40

Oakland

$352.20

Chicago

$236.18

Cheap SJC to MDW Flights

  • Question : Is there a day of the week that has more departure times to choose from than other days?
    Answer : The day with the most departure times for this route is Saturday with three options. Thursday currently offers the fewest number of flight times with two options.
  • Question : What is the cheapest day to fly to Chicago?
    Answer : As of May 20th, the best day for booking to Chicago (MDW) is May 22nd. A ticket will run you $316, which is 46% less than this route's average price.
  • Question : Is there an alternative airport near Chicago?
    Answer : Chicago Midway International Airport is a fine airport, but there is a cheaper option – O'Hare International Airport. It’s just 16 miles away and flights are being booked 30% cheaper over the coming two months.
  • Question : How long does it take to fly from San Jose to Chicago?
    Answer : Definitely the fastest option to get to Chicago when compared to walking. Flying from SJC to MDW can take as little as four hours and five minutes. Remember, there is a two-hour time change.
  • Question : How long do most people stay in Chicago?
    Answer : Of course, you are not most people, but if you were, you'd stay about one week.
  • Question : What is the cheapest day to fly?
    Answer : The cheapest day to fly from San Jose to Chicago is on Wednesday. So, if you are trying to save a bit of cash on your next vacation look for flights on that day.
  • Question : Which airline has the least delays from San Jose to Chicago?
    Answer : Booking with Delta Air Lines means you will arrive to Chicago approximately the time you were supposed to. In fact, this timely airline has a 100% on-time average. It never hurts to be prepared. If you should choose this airline, be sure to track the flight status to stay on top of the departure time.