$91 Cheap flight deals from San Jose (SJC) to Chicago (CHI)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

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.

Fri, Sep 26 - Mon, Sep 29
SJC
Norman Y. Mineta San Jose Intl.
ORD
O'Hare Intl.
$330 Roundtrip, found 1 hour ago
$330
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Sep 26 from Norman Y. Mineta San Jose Intl. to O'Hare Intl., returning Mon, Sep 29, priced at $330 found 1 hour ago
Sun, Sep 28 - Thu, Oct 9
SJC
Norman Y. Mineta San Jose Intl.
MDW
Midway Intl.
$330 Roundtrip, found 3 days ago
$330
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, Sep 28 from Norman Y. Mineta San Jose Intl. to Midway Intl., returning Thu, Oct 9, priced at $330 found 3 days ago
Sat, Sep 27 - Mon, Sep 29
OAK
Oakland Intl.
ORD
O'Hare Intl.
$477 Roundtrip, found 22 hours ago
$477
Roundtrip
found 22 hours ago
Select Alaska Airlines flight, departing Sat, Sep 27 from Oakland Intl. to O'Hare Intl., returning Mon, Sep 29, priced at $477 found 22 hours ago
Sun, Sep 28 - Fri, Oct 3
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$497 Roundtrip, found 1 day ago
$497
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Sep 28 from San Francisco Intl. to O'Hare Intl., returning Fri, Oct 3, priced at $497 found 1 day ago

Airfares from $91 One Way, $165 Round Trip from San Jose to Chicago

Prices starting at $165 for return flights and $91 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.

Mon, Nov 3 - Wed, Nov 5
SFO
San Francisco
ORD
Chicago
$165 Roundtrip, found 2 hours ago
$165
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Mon, Nov 3 from San Francisco to Chicago, returning Wed, Nov 5, priced at $165 found 2 hours ago
Mon, Oct 27 - Fri, Oct 31
SJC
San Jose
ORD
Chicago
$168 Roundtrip, found 7 hours ago
$168
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Mon, Oct 27 from San Jose to Chicago, returning Fri, Oct 31, priced at $168 found 7 hours ago
Sun, Oct 26 - Thu, Nov 6
SJC
San Jose
MDW
Chicago
$172 Roundtrip, found 3 days ago
$172
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, Oct 26 from San Jose to Chicago, returning Thu, Nov 6, priced at $172 found 3 days ago
Mon, Oct 27 - Thu, Oct 30
SFO
San Francisco
MDW
Chicago
$177 Roundtrip, found 9 hours ago
$177
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Mon, Oct 27 from San Francisco to Chicago, returning Thu, Oct 30, priced at $177 found 9 hours ago
Tue, Oct 28 - Wed, Oct 29
SFO
San Francisco
ORD
Chicago
$201 Roundtrip, found 10 hours ago
$201
Roundtrip
found 10 hours ago
Select Alaska Airlines flight, departing Tue, Oct 28 from San Francisco to Chicago, returning Wed, Oct 29, priced at $201 found 10 hours ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,427 reviews)

Nov 7 - Nov 11

4 night stay

San Jose (SJC) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach

Chicago (ORD) to San Jose (SJC)

Alaska Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,045, price is now $666 per person
$666
per person
found 1 day ago
One day didn’t receive room service

Reviewed on Sep 2, 2025

Swissotel - Chicago
4.5-star property

Swissotel - Chicago

9/10 Wonderful! (2,765 reviews)

Nov 7 - Nov 11

4 night stay

San Jose (SJC) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach

Chicago (ORD) to San Jose (SJC)

Alaska Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,106, price is now $715 per person
$715
per person
found 1 day ago
All around a great location with incredible views. We stayed in a king suite on the 30th floor with views of both the city and lake thanks to architect that designed the building as a triangle that overlooks the Chicago river.

Reviewed on Sep 3, 2025

Fairmont Chicago at Millennium Park
4.5-star property

Fairmont Chicago at Millennium Park

8.6/10 Excellent! (1,920 reviews)

Nov 7 - Nov 11

4 night stay

San Jose (SJC) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach

Chicago (ORD) to San Jose (SJC)

Alaska Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,039, price is now $694 per person
$694
per person
found 1 day ago
This property really wants to be a luxury hotel, but they repeatedly missed the mark. Everyone who worked there was really nice and apologetic, but they made promises they did not keep. One gets charged an "urban experience fee" of $25/ day for staying at this hotel. This fee gives you $15 towards food at the restaurants (which are okay, but the service is incredibly slow because there is only one kitchen across the restaurants), and the fee also covers guest passes to a health club that wasn't open during the times I was free, so I was basically forced to pay $25/ day for $15 credit towards their restaurants. My room had a nice view.

Reviewed on Sep 21, 2025

Don't see what you're looking for?
See all available trips from San Jose to Chicago
View all trips

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, Qantas, Royal Jordanian, Iberia, ANA, Brussels Airlines, Lufthansa, Gulf Air, British Airways
Earliest Flight Arrival
6:46PM UTC
Latest Flight Arrival
12:55PM UTC

San Jose to Chicago

If you are looking to get guaranteed low prices for San Jose to Chicago 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 San Jose to Chicago 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 San Jose to Chicago. We fine- tune your needs for San Jose to Chicago 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 San Jose to Chicago. You can also make changes to your schedule or even cancel a flight.

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.