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

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This Weekend's Flight Deals from Chicago to San Jose

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.

Sat, Jun 8 - Sat, Oct 19
MDW
Midway Intl.
SFO
San Francisco Intl.
$295 Roundtrip, found 2 days ago
$295
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Jun 8 from Midway Intl. to San Francisco Intl., returning Sat, Oct 19, priced at $295 found 2 days ago
Sun, Jun 9 - Tue, Jun 18
ORD
O'Hare Intl.
OAK
Oakland Intl.
$442 Roundtrip, found 1 day ago
$442
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Jun 9 from O'Hare Intl. to Oakland Intl., returning Tue, Jun 18, priced at $442 found 1 day ago
Sat, Jun 8 - Tue, Jun 11
ORD
O'Hare Intl.
SFO
San Francisco Intl.
$468 Roundtrip, just found
$468
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Jun 8 from O'Hare Intl. to San Francisco Intl., returning Tue, Jun 11, priced at $468 just found
Sat, Jun 8 - Wed, Jun 12
ORD
O'Hare Intl.
SJC
Norman Y. Mineta San Jose Intl.
$478 Roundtrip, found 17 hours ago
$478
Roundtrip
found 17 hours ago
Select Spirit Airlines flight, departing Sat, Jun 8 from O'Hare Intl. to Norman Y. Mineta San Jose Intl., returning Wed, Jun 12, priced at $478 found 17 hours ago

Airfares from $44 One Way, $88 Round Trip from Chicago to San Jose

Prices starting at $88 for return flights and $44 for one-way flights to San Jose were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Sep 11 - Sat, Sep 14
MDW
Chicago
SFO
San Francisco
$88 Roundtrip, just found
$88
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Sep 11 from Chicago to San Francisco, returning Sat, Sep 14, priced at $88 just found
Sat, Aug 31 - Tue, Sep 3
ORD
Chicago
SFO
San Francisco
$151 Roundtrip, found 4 hours ago
$151
Roundtrip
found 4 hours ago
Select United flight, departing Sat, Aug 31 from Chicago to San Francisco, returning Tue, Sep 3, priced at $151 found 4 hours ago
Tue, Sep 10 - Wed, Sep 11
ORD
Chicago
OAK
Oakland
$153 Roundtrip, found 2 days ago
$153
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Sep 10 from Chicago to Oakland, returning Wed, Sep 11, priced at $153 found 2 days ago
Tue, Sep 10 - Wed, Sep 11
ORD
Chicago
SJC
San Jose
$158 Roundtrip, found 3 days ago
$158
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Sep 10 from Chicago to San Jose, returning Wed, Sep 11, priced at $158 found 3 days ago
Fri, Aug 30 - Sun, Sep 1
ORD
Chicago
SFO
San Francisco
$189 Roundtrip, found 4 hours ago
$189
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Fri, Aug 30 from Chicago to San Francisco, returning Sun, Sep 1, priced at $189 found 4 hours ago

San Jose economy flight packages

Price found within the past 48 hours. Click for updated prices.
El Capitan Hotel
3.5-star property

El Capitan Hotel

9.4/10 Exceptional! (732 reviews)

Jul 19 - Jul 21

2 night stay

Chicago (CHI) to San Jose (SJC)

Frontier Airlines • Non-stop • Coach

San Jose (SJC) to Chicago (CHI)

Sun Country Airlines • Non-stop • Coach
per person
found 18 hours ago
Loved our stay. Thank you

Reviewed on Jun 2, 2024

The Ameswell Hotel
4.5-star property

The Ameswell Hotel

9.4/10 Exceptional! (662 reviews)

Jul 19 - Jul 21

2 night stay

Chicago (CHI) to San Jose (SJC)

Frontier Airlines • Non-stop • Coach

San Jose (SJC) to Chicago (CHI)

Sun Country Airlines • Non-stop • Coach
per person
found 18 hours ago
modern with new design

Reviewed on Dec 4, 2023

Shashi Hotel Mountain View Palo Alto
5.0-star property

Shashi Hotel Mountain View Palo Alto

9.4/10 Exceptional! (572 reviews)

Jul 19 - Jul 21

2 night stay

Chicago (CHI) to San Jose (SJC)

Frontier Airlines • Non-stop • Coach

San Jose (SJC) to Chicago (CHI)

Sun Country Airlines • Non-stop • Coach
per person
found 18 hours ago
The Front Desk folks are fantastic.

Reviewed on Mar 17, 2024

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More About Flying To San Jose from Chicago

Route Information for Flights from Chicago to San Jose

Origin Airport IATA Code
CHI
Destination Airport IATA Code
SJC
Distance
1842 mi
Direct Flight Airlines
American Airlines, Qatar Airways, Air Canada, JAL, Fiji Airways, Austrian, Aer Lingus, Emirates, Asiana Airlines, Virgin Australia, Air New Zealand, United Airlines, Alaska Airlines, Qantas, China Southern Airlines, Royal Jordanian, Iberia, ANA, Brussels Airlines, Lufthansa, Singapore Airlines, Gulf Air, British Airways
Earliest Flight Arrival
8:59PM UTC
Latest Flight Arrival
7:59AM UTC

Chicago to San Jose

If you are looking to get guaranteed low prices for Chicago to San Jose flights then Orbitz is the place to go. We use cutting edge mobile tools to find the best deals on air tickets and to keep you updated on delays and changes.

Get Package Savings by Booking Flights and Hotels at the Same Time

Using the Orbitz Matrix display, you can see how much you will save on flights from Chicago to San Jose if the discount fare is combined with a hotel. You can also look at hotel reviews, photos and maps of the area, so it will be convenient to make your budget travel plans.

Orbitz for Business Helps Corporations save Money

Orbitz can assist all businesses from the small to major corporations with discounts on flights from Chicago to San Jose. We fine- tune your needs for Chicago to San Jose flights and optimize your plans by assessing your business and coming up with ways for you to save on air tickets.

Using Online Check-In Makes Flying Simple

You can use the Orbitz website to check-in for your flights from Chicago to San Jose. You can also make changes to your schedule or even cancel a flight.

Frequently asked questions

Are there non-stop flights from Chicago to San Jose?
You’re in luck — you’ll find 3 airlines which fly nonstop between O’Hare Airport and San Francisco, CA (SFO-San Francisco Intl.). Here are some of the most popular:

  • United Airlines
  • American Airlines
  • Alaska Airlines

What is the shortest flight from Chicago to San Jose?
Jetting from O’Hare Airport to San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) will take you at least 5 hours and 5 minutes. Indulge in a tipple and watch a movie or two — now’s your chance to just relax.
What airlines fly from Chicago to San Jose most frequently?
There are a few airlines offering frequent flights from O’Hare Intl. Airport (ORD) to SFO, including United Airlines (UA). The preferred choice of many travelers, it operates 243 flights on this route each month. American Airlines (AA) will also take you to your destination in comfort and style. Offering 126 flights every month between Chicago and San Jose, it’s another popular airline to look into.
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.