$49 Cheap flight deals from San Jose (SJC) to Chicago (CHI)

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Airfares from $49 One Way, $98 Round Trip from San Jose to Chicago

Prices starting at $98 for return flights and $49 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

More About Flying To Chicago from San Jose

Route Information for Flights from San Jose to Chicago

Origin Airport IATA Code
SJC
Destination Airport IATA Code
CHI
Distance
1842 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Air Canada, Aer Lingus, Emirates, Asiana Airlines, Virgin Australia, Air New Zealand, United Airlines, Alaska Airlines, Frontier Airlines, Qantas, SAS, Royal Jordanian, Iberia, ANA, Brussels Airlines, Lufthansa, Singapore Airlines, Gulf Air, British Airways
Earliest Flight Arrival
1:30PM UTC
Latest Flight Arrival
1:20PM UTC

San Jose to Chicago

Orbitz can provide you with the greatest deals on a wide range of San Jose to Chicago flights. Orbitz offers guaranteed low prices and offers you the convenience of cutting-edge mobile tools thus providing you with your best travel experience ever.

Mobile Apps for San Jose to Chicago Flights

You can use our mobile app to find the cheapest prices for flights from San Jose to Chicago. With this cutting-edge technology, you can check up on your flight’s status, gate number and luggage claim handling, and reserve exclusive deals on top hotels at short notice.

Loyalty Rewarded

For travelers who regularly book San Jose to Chicago flights, our frequent flyer program offers even more low-cost air tickets. You will be able to store your miles in your personal Orbitz account and add them with ease to your future reservations.

Trouble-Free Traveling With Flight Alerts

Orbitz will not only provide you with the assistance that you require when purchasing flights from San Jose to Chicago but will ensure that you remain fully updated on any flight delays, changes or disruptions by providing free alerts. Your San Jose to Chicago flights alerts can be sent directly to your phone or email. You can also opt for these alerts to be sent to your family and friends so that everyone is kept informed of your travel plans.

 Budget Flying Made Simple

Finding cheap flights from San Jose to Chicago is easy with Orbitz. You can pick and choose airlines for your international flights to create inexpensive yet convenient travel arrangements.

Frequently asked questions

Are there non-stop flights from San Jose to Chicago?
Yep, your amazing getaway is just one simple flight away. Fantastic news, isn’t it? Book your favorite seat aboard one of the 3 carriers that fly direct from San Francisco Airport to Chicago, IL (ORD-O’Hare Intl.). Popular picks include:

  • United Airlines
  • American Airlines
  • Alaska Airlines

What is the shortest flight from San Jose to Chicago?
The fastest flight from San Jose Intl. Airport to O’Hare Airport is 4 hours and 40 minutes. Slip a few things into your hand luggage to keep you out of mischief, like an interesting read or some playing cards.
What airlines fly from San Jose to Chicago most frequently?
United Airlines (UA) is one of the airlines with the most flights from San Francisco Intl. Airport (SFO) to Chicago, IL (ORD-O’Hare Intl.). It offers 243 services on this route every month. Going on vacation is one of life’s biggest pleasures, and this airline will get you to your destination quickly and safely. Also consider the fares available with American Airlines (AA). Offering 126 flights every month between San Jose and Chicago, they’ll make sure your journey is just as good as the destination.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.