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Cheap SJC to ORD Flights

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

San Jose to Chicago route information

Origin Airport Norman Y. Mineta San Jose Intl.
Destination Airport O'Hare Intl.
Airlines Serving Alaska Airlines, American Airlines, Delta, Frontier Airlines, JetBlue Airways, United
Flight Price $224
Distance 1,824 mi



San Francisco




Cheap SJC to ORD Flights

  • How long is the flight from SJC to ORD?

    United Airlines can get you there in four hours and three minutes. For example, if you were to leave San Jose at 6:40 AM PDT, you would get to Chicago at 12:43 PM CDT. Just enough time to catch up on your television shows before your plane lands (remember, there is a time change of two hours).
  • What day of the week has the most flight time options?

    Sunday has the greatest variety of flight times for San Jose to Chicago with eight. The day of the week with the fewest number of times is Wednesday with only four options.
  • How many flights are there per day from San Jose to Chicago?

    Depending on the day of the week, the number of flight times will change, but on average there are five. The average route departing the United States currently has nine different flight times per day, so expect fewer options than you're used to.
  • What is the cheapest day to fly?

    The cheapest day to fly from San Jose to Chicago is on Tuesday. If you want to save a bit of money on your next business trip look for flights on that day.
  • Which airline has the least delays from San Jose to Chicago?

    Booking with United Airlines means you will arrive to Chicago around the time you were supposed to. In fact, this timely airline has an 84% on-time average. Of course, it never hurts to be prepared. If you're on Delta Air Lines, be sure to sign up for the delay notifications to stay up to date with your flight's status.
  • What is the cheapest day to fly to Chicago?

    As of Sep 16th, the best day for deals to Chicago (ORD) is Oct 2nd. Your ticket will cost $230, which is 35% below the average price to book the same route.
  • How much is a plane ticket to Chicago (ORD) from San Jose (SJC)?

    Cost can range from $230 to $1,042, prices for SJC to ORD fluctuate less than the majority of routes in the United States. Prices are usually lower the further out you book.

San Jose to Chicago 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 San Jose to Chicago 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 Chicago.

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 SJC to ORD flights that won’t make your bank account wince. Ready to temporarily leave behind San Jose 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 ORD 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.

Sep 9, 2019

Seats need to be wider for bigger people

Jul 28, 2019

Flight on time

Jul 16, 2019

Best landing ever!

Jul 5, 2019

Captain kept us informed during delays.

Jun 27, 2019

Our flight was early into Chicago and we had to wait 30 minutes for a gate.

Jun 4, 2019

Great Trip!

Jan 25, 2019

Best flight ever

Jan 11, 2019

Seats are still cramped and uncomfortable, no room for elbows and very difficult to cross legs because there's very little leg room.And I'm a regular size person. Also the bathrooms are extremely small. Otherwise the service was excellent!

Dec 25, 2018

Smooth all around

Dec 17, 2018