$53 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, Aug 9 - Wed, Aug 13
SFO
San Francisco Intl.
MDW
Midway Intl.
$246 Roundtrip, found 1 day ago
$246
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Aug 9 from San Francisco Intl. to Midway Intl., returning Wed, Aug 13, priced at $246 found 1 day ago
Sun, Aug 10 - Sat, Aug 23
SJC
Norman Y. Mineta San Jose Intl.
ORD
O'Hare Intl.
$323 Roundtrip, found 12 hours ago
$323
Roundtrip
found 12 hours ago
Select Spirit Airlines flight, departing Sun, Aug 10 from Norman Y. Mineta San Jose Intl. to O'Hare Intl., returning Sat, Aug 23, priced at $323 found 12 hours ago
Sat, Aug 9 - Tue, Aug 12
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$332 Roundtrip, found 8 hours ago
$332
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, Aug 9 from San Francisco Intl. to O'Hare Intl., returning Tue, Aug 12, priced at $332 found 8 hours ago
Fri, Aug 8 - Sat, Aug 23
OAK
Oakland Intl.
ORD
O'Hare Intl.
$403 Roundtrip, found 15 hours ago
$403
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Fri, Aug 8 from Oakland Intl. to O'Hare Intl., returning Sat, Aug 23, priced at $403 found 15 hours ago

Airfares from $53 One Way, $114 Round Trip from San Jose to Chicago

Prices starting at $114 for return flights and $53 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.

Wed, Sep 3 - Tue, Sep 9
SJC
San Jose
ORD
Chicago
$114 Roundtrip, found 9 hours ago
$114
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Wed, Sep 3 from San Jose to Chicago, returning Tue, Sep 9, priced at $114 found 9 hours ago
Wed, Sep 3 - Wed, Sep 10
OAK
Oakland
ORD
Chicago
$115 Roundtrip, found 11 hours ago
$115
Roundtrip
found 11 hours ago
Select Spirit Airlines flight, departing Wed, Sep 3 from Oakland to Chicago, returning Wed, Sep 10, priced at $115 found 11 hours ago
Thu, Sep 4 - Mon, Sep 8
SFO
San Francisco
MDW
Chicago
$164 Roundtrip, found 11 hours ago
$164
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Thu, Sep 4 from San Francisco to Chicago, returning Mon, Sep 8, priced at $164 found 11 hours ago
Wed, Sep 10 - Wed, Oct 1
SFO
San Francisco
ORD
Chicago
$176 Roundtrip, found 5 hours ago
$176
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Wed, Sep 10 from San Francisco to Chicago, returning Wed, Oct 1, priced at $176 found 5 hours ago
Tue, Aug 26 - Sat, Aug 30
SFO
San Francisco
ORD
Chicago
$191 Roundtrip, found 2 days ago
$191
Roundtrip
found 2 days ago
Select United flight, departing Tue, Aug 26 from San Francisco to Chicago, returning Sat, Aug 30, priced at $191 found 2 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Chicago/Alsip
2.5-star property

Baymont by Wyndham Chicago/Alsip

8.2/10 Very Good! (1,011 reviews)

Sep 6 - Sep 9

3 night stay

San Jose (SJC) to Chicago (MDW)

Spirit Airlines • Non-stop roundtrip • Coach
per person
found 3 hours ago
My second stay here and I’m totally satisfied with this hotel. It’s clean, comfortable and staff friendly and helpful

Reviewed on Mar 27, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,659 reviews)

Sep 12 - Sep 14

2 night stay

San Jose (SJC) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 15 hours ago
This is the nicest hotel that I have ever stayed at. Everything was perfect!

Reviewed on Jun 16, 2025

Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

9.6/10 Exceptional! (1,000 reviews)

Sep 12 - Sep 14

2 night stay

San Jose (SJC) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • Coach
per person
found 15 hours ago
From the moment you walk into their lobby at the hotel, you enter a place of calm and relaxation. We stayed in a room with the Water Tower view, and if you have that as the option, take it. It was a beautiful sight to see waking up every morning. This hotel like their other properties are in a class of their own.

Reviewed on Sep 13, 2024

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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, Aer Lingus, Austrian, Emirates, Asiana Airlines, Virgin Australia, Air New Zealand, United Airlines, Alaska Airlines, Qantas, Finnair, Royal Jordanian, Iberia, Hawaiian Airlines, ANA, Brussels Airlines, Lufthansa, Singapore Airlines, Gulf Air, British Airways
Earliest Flight Arrival
6:27PM UTC
Latest Flight Arrival
1:15PM UTC

San Jose to Chicago

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Your Perfect ChicagoVacation Package

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Low Price Guarantee

With the best deals and easy searching options, Orbitz make it easy and fun to find cheap San Jose to Chicago flights, a great hotel, or a full vacation package. With Orbitz’s low price guarantee, you always get great discounts on air ticket prices.

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.