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Cheap Flights from Chicago to San Jose $297.89

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

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

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

Question : In the next four weeks, what day should you book your trip?
Answer : As of January 16th, the best day for deals to San Jose (SJO) from Chicago (MDW) is February 1st. Bookings have been made roughly 24% below the average price for this route.

Question : Is Chicago Midway International Airport (MDW) the cheapest airport for getting to Juan Santamaria International Airport (SJO)?
Answer : Luckily for you, there is another airport nearby. O'Hare International Airport (ORD) is 16 miles away, and over the next few months, flights are 28% cheaper than those from Chicago Midway International Airport.

Question : How long are most people's visits to San Jose when they fly in from Chicago?
Answer : The average time spent in San Jose by passengers flying from MDW is eight days.

Question : Would you be willing to change your travel days if it saved you money?
Answer : The cheapest day to fly in February is Wednesday. Being flexible with your travel days garners you even more savings during your booking.

Question : Which airline is offering the cheapest round-trip flight from MDW to SJO?
Answer : Delta Air Lines has been booking passengers at the cheapest fare for flights scheduled throughout the next three months.