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Cheap MDW to SJC Flights

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



San Francisco




Cheap MDW to SJC Flights

Question : What is the cheapest day to fly to San Jose?
Answer : Jan 27th has bookings (as of Jan 22nd) for as little as $264. That comes in 41% below the average price. Saving on flight fares gives you more cash in your hand.

Question : How much is a plane ticket to San Jose (SJC) from Chicago (MDW)?
Answer : Cost can range from $264 to $887, prices for MDW to SJC fluctuate less than most routes in the United States. Prices tend to be cheaper the further out you book.

Question : How long does it take to fly from Chicago to San Jose?
Answer : Definitely the fastest option to get to San Jose when compared to taking the train. Flying from MDW to SJC typically takes about four hours and 45 minutes. Remember, there is a time change of two hours.

Question : Can I change the date of my flight?
Answer : Yes, you can switch your departure date. If you wish to save a little money in doing so, the lowest-cost day to fly in February is Monday. You may be thinking you're missing out leaving a day earlier, but we see it as just adding saving towards a future holiday.

Question : What is the cheapest airline flying from Chicago to San Jose?
Answer : Delta Air Lines strives to keep prices down for their passengers over the next three months. Bookings are being made at just $264, which is quite a deal when compared to the high-end bookings of $887.

Question : What airports do you fly into for San Jose?
Answer : Fortunately, there is another way to get to San Jose from Chicago. O'Hare International Airport (ORD) is only 16 miles away, and over the upcoming months, flights are being priced 33% cheaper than flights from Chicago Midway International Airport.

Question : How long is the flight from MDW to SJC?
Answer : Southwest Airlines currently holds the fastest travel time with four hours and 40 minutes. So, you would arrive in San Jose at 11:30 AM PST if you left Chicago at 8:50 AM CST. Remember, there is a two-hour time change.

Chicago to San Jose Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Chicago to San Jose will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring San Jose.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at, we’ll pair you up with MDW to SJC flights that won’t make your bank account wince. Ready to temporarily leave behind Chicago for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to SJC with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.