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Cheap Flights from Chicago to San Jose $312.72

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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 : Looking for the cheapest flight over the next 30 days?
Answer : As of December 5th, the cheapest day to fly from Chicago to San Jose is January 3rd. Tickets have been sold for 33% below the average price for this route.

Question : Have you considered flying out of an airport besides Chicago Midway International Airport (MDW)?
Answer : Try searching for flights from O'Hare International Airport (ORD) as well. Over the next two months, flights from ORD to SJO are being booked 32% cheaper than flights from MDW to SJO. Being only 16 miles away, it's easily accessible for most.

Question : How long do most people stay in San Jose when they fly in from Chicago?
Answer : The average time spent in San Jose by travelers flying from MDW is eight days.

Question : Would you be willing to change your travel days if it saved you money?
Answer : Sunday is your lowest-cost day to fly in December. Flexibility is paramount when booking travel plans in order to keep costs down.

Question : Over the coming months, which airline is getting its passengers to Juan Santamaria International Airport (SJO) round-trip the cheapest?
Answer : Delta Air Lines has been booking passengers at the cheapest fare for flights scheduled throughout the next three months.