$85 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.

Fri, Jun 20 - Mon, Jun 23
SFO
San Francisco Intl.
MDW
Midway Intl.
$350 Roundtrip, found 8 hours ago
$350
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Fri, Jun 20 from San Francisco Intl. to Midway Intl., returning Mon, Jun 23, priced at $350 found 8 hours ago
Fri, Jun 20 - Tue, Jul 1
OAK
Oakland Intl.
ORD
O'Hare Intl.
$393 Roundtrip, found 7 hours ago
$393
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Fri, Jun 20 from Oakland Intl. to O'Hare Intl., returning Tue, Jul 1, priced at $393 found 7 hours ago
Fri, Jun 20 - Tue, Jun 24
OAK
Oakland Intl.
MDW
Midway Intl.
$427 Roundtrip, found 4 days ago
$427
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Jun 20 from Oakland Intl. to Midway Intl., returning Tue, Jun 24, priced at $427 found 4 days ago
Sun, Jun 22 - Fri, Jun 27
SJC
Norman Y. Mineta San Jose Intl.
MDW
Midway Intl.
$467 Roundtrip, found 6 days ago
$467
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sun, Jun 22 from Norman Y. Mineta San Jose Intl. to Midway Intl., returning Fri, Jun 27, priced at $467 found 6 days ago

Airfares from $85 One Way, $162 Round Trip from San Jose to Chicago

Prices starting at $162 for return flights and $85 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, Jun 30 - Sat, Jul 19
OAK
Oakland
ORD
Chicago
$162 Roundtrip, found 6 days ago
$162
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Mon, Jun 30 from Oakland to Chicago, returning Sat, Jul 19, priced at $162 found 6 days ago
Wed, Jul 9 - Tue, Jul 22
SJC
San Jose
ORD
Chicago
$176 Roundtrip, found 6 days ago
$176
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, Jul 9 from San Jose to Chicago, returning Tue, Jul 22, priced at $176 found 6 days ago
Wed, Sep 10 - Tue, Sep 16
SFO
San Francisco
ORD
Chicago
$179 Roundtrip, found 14 hours ago
$179
Roundtrip
found 14 hours ago
Select United flight, departing Wed, Sep 10 from San Francisco to Chicago, returning Tue, Sep 16, priced at $179 found 14 hours ago
Wed, Oct 15 - Sat, Oct 18
SFO
San Francisco
ORD
Chicago
$179 Roundtrip, found 4 days ago
$179
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Oct 15 from San Francisco to Chicago, returning Sat, Oct 18, priced at $179 found 4 days ago
Sat, Sep 20 - Thu, Sep 25
OAK
Oakland
MDW
Chicago
$198 Roundtrip, found 3 days ago
$198
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Sep 20 from Oakland to Chicago, returning Thu, Sep 25, priced at $198 found 3 days ago

Chicago economy flight packages

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

Congress Plaza Hotel

8/10 Very Good! (8,858 reviews)

Aug 7 - Aug 12

5 night stay

San Jose (SJC) to Chicago (ORD)

Spirit Airlines • Non-stop • Coach

Chicago (ORD) to San Jose (SJC)

American Airlines • Non-stop • Coach
per person
found 11 hours ago
It’s was easy- we were in our rooms within a Few minutes of arriving

Reviewed on Jun 1, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
4.0-star property

The Allegro Royal Sonesta Hotel Chicago Loop

8.8/10 Excellent! (1,771 reviews)

Aug 7 - Aug 12

5 night stay

San Jose (SJC) to Chicago (ORD)

Spirit Airlines • Non-stop • Coach

Chicago (ORD) to San Jose (SJC)

American Airlines • Non-stop • Coach
Save 100% on your flight
per person
found 11 hours ago
Attitude of the people was outstanding!! Very friendly and helpful.

Reviewed on Jun 13, 2025

Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

8.2/10 Very Good! (1,759 reviews)

Aug 7 - Aug 12

5 night stay

San Jose (SJC) to Chicago (ORD)

Spirit Airlines • Non-stop • Coach

Chicago (ORD) to San Jose (SJC)

American Airlines • Non-stop • Coach
per person
found 11 hours ago
Great location for doing things downtown. Walkable to every where one wants to go, or a cheap Lyft ride.

Reviewed on May 1, 2025

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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, Hawaiian Airlines, Iberia, ANA, Brussels Airlines, Lufthansa, Singapore Airlines, Gulf Air, British Airways
Earliest Flight Arrival
5:56PM UTC
Latest Flight Arrival
1:19PM UTC

San Jose to Chicago

Orbitz gives you great deals on your flights from San Jose to Chicago. If you also need a discount car rental or a cheap hotel room after you arrived at your destination, Orbitz has you covered.

We Offer Great Travel Deals and Discounts

When you book flights from San Jose to Chicago with Orbitz for, you can be assured that you are getting the lowest price possible. Orbitz works constantly with our airline partners to ensure guaranteed low prices on San Jose to Chicago flights for your trip—whether you are traveling for business or for fun with your family.

Enjoy Savings on Last-Minute Flights

If you are looking for a discount price on last-minute flights from San Jose to Chicago, chances are that Orbitz can offer you a deal that will save you lots of money. Whether you just want to get away for the weekend or go on a vacation lasting weeks, Orbitz can help you find the best deals on San Jose to Chicago flights that fit your budget and your itinerary for the perfect trip.

Full-Service Mobile Apps

Need more mobility when it comes to travel planning? Orbitz has easy-to-use mobile apps for iPhone, iPad, and Android, to help the traveler on the go. Not only can use the apps to find huge savings on San Jose to Chicago flights wherever you are, but you can also check out and book discount hotel rooms too. The apps will also keep you up-to-date when it’s time to fly. Get easy access to your itinerary for flights from San Jose to Chicago and review gate and baggage claim details too.

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.