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Cheap Flights from San Jose to Chicago $246.27

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Cheapest Flights from San Jose to Chicago (SJC to MDW)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from San Jose to Chicago (SJC to MDW)

Question : If your plans are flexible, have you considered changing your departure day?
Answer : The best day to fly on a budget this month is Monday. Having flexibility in your travel plans means you can save, so be sure to plan ahead when possible.

Question : Do travelers from San Jose typically stay in Chicago for very long?
Answer : Passengers from SJC to MDW stay five days on average.

Question : Which airline is least likely to get you to MDW on time?
Answer : If you decide to book your flight with XOJET, keep an eye on your departure time. Over the past month, XOJET flights from Norman Y. Mineta San Jose International Airport (SJC) to Chicago Midway International Airport (MDW) are delayed 100% of the time.

Question : Is there another local airport that can get you to Chicago?
Answer : Metropolitan Oakland International Airport (OAK) is just 29 miles away, and, on average, flights are 14% cheaper for the next two months. Save now and put it toward your next adventure.