$49 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.

Sat, May 4 - Wed, May 8
SFO
San Francisco Intl.
MDW
Midway Intl.
$168 Roundtrip, found 18 hours ago
$168
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Sat, May 4 from San Francisco Intl. to Midway Intl., returning Wed, May 8, priced at $168 found 18 hours ago
Sat, May 4 - Tue, May 7
OAK
Oakland Intl.
ORD
O'Hare Intl.
$308 Roundtrip, just found
$308
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, May 4 from Oakland Intl. to O'Hare Intl., returning Tue, May 7, priced at $308 just found
Sat, May 4 - Tue, May 7
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$351 Roundtrip, just found
$351
Roundtrip
just found
Select Alaska Airlines flight, departing Sat, May 4 from San Francisco Intl. to O'Hare Intl., returning Tue, May 7, priced at $351 just found
Sun, May 5 - Sat, May 11
SJC
Norman Y. Mineta San Jose Intl.
ORD
O'Hare Intl.
$481 Roundtrip, just found
$481
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, May 5 from Norman Y. Mineta San Jose Intl. to O'Hare Intl., returning Sat, May 11, priced at $481 just found

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.

Sat, May 11 - Sat, May 18
SFO
San Francisco
MDW
Chicago
$98 Roundtrip, just found
$98
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 11 from San Francisco to Chicago, returning Sat, May 18, priced at $98 just found
Wed, May 15 - Tue, May 28
SJC
San Jose
ORD
Chicago
$106 Roundtrip, found 4 days ago
$106
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, May 15 from San Jose to Chicago, returning Tue, May 28, priced at $106 found 4 days ago
Sun, May 26 - Tue, Jun 4
OAK
Oakland
ORD
Chicago
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Sun, May 26 from Oakland to Chicago, returning Tue, Jun 4, priced at $119 found 1 day ago
Tue, Jun 11 - Wed, Jun 12
SFO
San Francisco
ORD
Chicago
$173 Roundtrip, found 7 hours ago
$173
Roundtrip
found 7 hours ago
Select Alaska Airlines flight, departing Tue, Jun 11 from San Francisco to Chicago, returning Wed, Jun 12, priced at $173 found 7 hours ago
Tue, Sep 3 - Sat, Sep 7
SFO
San Francisco
ORD
Chicago
$186 Roundtrip, found 21 hours ago
$186
Roundtrip
found 21 hours ago
Select United flight, departing Tue, Sep 3 from San Francisco to Chicago, returning Sat, Sep 7, priced at $186 found 21 hours ago

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, 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 has your best deals on San Jose to Chicago flights. From guaranteed low prices to cutting-edge mobile tools, the perfect trip begins on Orbitz.
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Budget Travel Planning Made Easy

It's easy to find discount air tickets for flights from San Jose to Chicago on Orbitz. Mix and match airlines for your departing and your returning flights to find the lowest fares and the best schedule.

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.