$69 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, Jun 8 - Wed, Jul 3
SFO
San Francisco Intl.
MDW
Midway Intl.
$179 Roundtrip, found 22 hours ago
$179
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Sat, Jun 8 from San Francisco Intl. to Midway Intl., returning Wed, Jul 3, priced at $179 found 22 hours ago
Sun, Jun 9 - Tue, Jun 11
OAK
Oakland Intl.
ORD
O'Hare Intl.
$220 Roundtrip, just found
$220
Roundtrip
just found
Select Sun Country Airlines flight, departing Sun, Jun 9 from Oakland Intl. to O'Hare Intl., returning Tue, Jun 11, priced at $220 just found
Sun, Jun 9 - Tue, Jun 11
SJC
Norman Y. Mineta San Jose Intl.
ORD
O'Hare Intl.
$246 Roundtrip, just found
$246
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, Jun 9 from Norman Y. Mineta San Jose Intl. to O'Hare Intl., returning Tue, Jun 11, priced at $246 just found
Sun, Jun 9 - Wed, Jun 12
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$312 Roundtrip, just found
$312
Roundtrip
just found
Select Sun Country Airlines flight, departing Sun, Jun 9 from San Francisco Intl. to O'Hare Intl., returning Wed, Jun 12, priced at $312 just found

Airfares from $69 One Way, $138 Round Trip from San Jose to Chicago

Prices starting at $138 for return flights and $69 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.

Tue, Aug 27 - Tue, Sep 10
OAK
Oakland
ORD
Chicago
$138 Roundtrip, found 6 days ago
$138
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Tue, Aug 27 from Oakland to Chicago, returning Tue, Sep 10, priced at $138 found 6 days ago
Tue, Sep 3 - Sat, Sep 7
SFO
San Francisco
ORD
Chicago
$151 Roundtrip, just found
$151
Roundtrip
just found
Select United flight, departing Tue, Sep 3 from San Francisco to Chicago, returning Sat, Sep 7, priced at $151 just found
Tue, Sep 10 - Wed, Sep 11
SJC
San Jose
ORD
Chicago
$153 Roundtrip, found 3 days ago
$153
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Sep 10 from San Jose to Chicago, returning Wed, Sep 11, priced at $153 found 3 days ago
Wed, Aug 14 - Mon, Aug 19
SJC
San Jose
MDW
Chicago
$190 Roundtrip, found 2 hours ago
$190
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Aug 14 from San Jose to Chicago, returning Mon, Aug 19, priced at $190 found 2 hours ago
Sun, Jul 14 - Thu, Jul 18
OAK
Oakland
ORD
Chicago
$195 Roundtrip, found 12 hours ago
$195
Roundtrip
found 12 hours ago
Select Sun Country Airlines flight, departing Sun, Jul 14 from Oakland to Chicago, returning Thu, Jul 18, priced at $195 found 12 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, Aer Lingus, Austrian, Emirates, Asiana Airlines, Virgin Australia, Air New Zealand, United Airlines, Alaska Airlines, Qantas, China Southern Airlines, Royal Jordanian, Finnair, Iberia, ANA, Brussels Airlines, Lufthansa, Singapore Airlines, Air China, Gulf Air, British Airways
Earliest Flight Arrival
7:19PM UTC
Latest Flight Arrival
1:15PM UTC

San Jose to Chicago

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Take advantage of low fares on San Jose to Chicago flights and vacation packages

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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.