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Cheap ORD to SJO Flights

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

Chicago to San Jose route information

Origin Airport O'Hare Intl.
Destination Airport Juan Santamaria Intl.
Airlines Serving Aeromexico, Air Canada, Alaska Airlines, American Airlines, Avianca, Copa, Delta, Interjet, JetBlue Airways, Spirit Airlines, United
Flight Price $263
Distance 2,220 mi



Cheap ORD to SJO Flights

  • Which airline has the least delays from Chicago to San Jose?

    United Airlines holds the best record for flights from ORD to SJO with an 83% on-time rate. If they are delayed for some reason.
  • What is the cheapest day to fly?

    The cheapest day to fly from Chicago to San Jose is on Wednesday. If you want to save some money on your next holiday look for flights on Wednesday.
  • How many flights are there per day from Chicago to San Jose?

    The number does differ by the day, but on average, you can expect two different choices of flight times when you book. Compared to the average route departing the United States with nine flight times, you'll have fewer options.
  • How much time do people spend in San Jose?

    The average time spent sightseeing in San Jose by passengers from Chicago is seven days.
  • How much is a plane ticket to San Jose (SJO) from Chicago (ORD)?

    Cost can range from $262 to $1,911, prices for ORD to SJO fluctuate less than most routes from the United States. The further out you book, the more likely you are to save on your trip.
  • How long is the flight from ORD to SJO?

    United Airlines currently holds the quickest travel time with five hours and 15 minutes. So, you would arrive in San Jose at 10:45 PM CST if you left Chicago at 5:30 PM CDT.
  • Can I change the date of my flight?

    You sure can switch your departure date and you may save yourself some money by changing when you take off. The cheapest day to fly in October is Wednesday.

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 ORD to SJO 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 SJO 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.

Feb 7, 2019

Economy plus

Apr 1, 2017

Seats very crowded.

Jan 8, 2017

Did NOT like 9 hour layover.