$44 Cheap flight deals from San Jose (SJC) to Chicago (CHI)

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This Weekend's Flight Deals from San Jose to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Airfares from $44 One Way, $146 Round Trip from San Jose to Chicago

Prices starting at $146 for return flights and $44 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.

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago
LondonHouse Chicago, Curio Collection by Hilton
Trump International Hotel & Tower Chicago
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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, Austrian, Aer Lingus, Emirates, Asiana Airlines, Virgin Australia, Air New Zealand, United Airlines, Alaska Airlines, Qantas, China Southern Airlines, Finnair, Royal Jordanian, Iberia, ANA, Brussels Airlines, Lufthansa, Air China, Singapore Airlines, Gulf Air, British Airways
Earliest Flight Arrival
7:19PM UTC
Latest Flight Arrival
1:15PM UTC

San Jose to Chicago

The best fares for San Jose to Chicago flights are always found on Orbitz. With superior discounts and the latest innovations in mobile access, your ideal trip starts with Orbitz.

The Easy Way to Plan Travel Cheaply

We provide access to many low-cost vacation packages and travelers can mix and match airlines when scheduling their flights for the best prices and flight times. Finding cheap tickets on flights from San Jose to Chicago is easy when you make Orbitz your #1 travel planner.

Book San Jose to Chicago Flights With Mobile Apps

Our iPhone and Android mobile apps can be used to compare and book flights from San Jose to Chicago. These apps are perfect for checking the status of flights, gate and baggage claims details, car rental rates, and for receiving alerts on special savings that are exclusive to mobile users. Mobile app users can even score great rates when booking hotel rooms. You can compare hotels, virtually view photo galleries, and check out user reviews using the app, as well as find out which ones are closest to you.

Orbitz also offers free travel updates that are sent to your email or mobile phone that notifies you of booking changes, disruptions in service, or delayed flights.

Increase Your Rewards While Enjoying Super Low Rates

Boost your points or miles for your frequent flyer program on certain San Jose to Chicago flights. Simply provide your frequent flyer information when booking flights from San Jose to Chicago with Orbitz and get both a low fare and travel rewards. You can enter this information in your Orbitz account profile for easy remembering in future bookings.

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.