HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
San Jose

$60+ Cheap flights from Chicago (CHI) to San Jose, CA (SJC)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJC
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to San Jose with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to San Jose are usually found in February or October, booked 2 days in advance, depart on a Wednesday or Thursday and return on a Tuesday

Cheap flight deals from Chicago to San Jose

Cheapest flights from Chicago to San Jose
Explore the most affordable flight options available from Chicago to San Jose. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 4, 2025.

This KAYAK deal was found by Cheapflights users on 12/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/152:05 pmORD - SJC
1 stop7h 19mAlaska Airlines
Wed 1/712:46 pmSJC - ORD
1 stop8h 51mAlaska Airlines
Deal found 12/1$270
This Alaska Airlines deal was found by Cheapflights users on 12/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/178:55 amORD - SJC
1 stop7h 37mAlaska Airlines
Tue 1/68:00 pmSJC - ORD
1 stop16h 29mAlaska Airlines
Deal found 12/2$286
This Kiwi.com deal was found by Cheapflights users on 12/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:44 pmORD - SJC
1 stop20h 48mMultiple Airlines
Thu 12/257:43 pmSJC - ORD
1 stop8h 22mMultiple Airlines
Deal found 12/4$295
This Alaska Airlines deal was found by Cheapflights users on 12/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:00 amORD - SJC
1 stop9h 52mAlaska Airlines
Wed 1/712:46 pmSJC - ORD
1 stop8h 51mAlaska Airlines
Deal found 12/3$297
This Alaska Airlines deal was found by Cheapflights users on 12/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/178:55 amORD - SJC
1 stop10h 42mAlaska Airlines
Thu 1/82:59 pmSJC - ORD
1 stop6h 38mAlaska Airlines
Deal found 12/3$298
This Kiwi.com deal was found by Cheapflights users on 12/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:00 amORD - SJC
2 stops13h 48mMultiple Airlines
Thu 12/257:43 pmSJC - ORD
1 stop8h 22mMultiple Airlines
Deal found 12/2$306
This CheapOair deal was found by Cheapflights users on 12/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1212:59 pmORD - SJC
1 stop8h 14mFrontier
Sun 12/143:27 pmSJC - ORD
1 stop18h 15mFrontier
Deal found 12/2$308
This Alaska Airlines deal was found by Cheapflights users on 12/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:00 amORD - SJC
1 stop9h 52mAlaska Airlines
Thu 1/82:59 pmSJC - ORD
1 stop6h 38mAlaska Airlines
Deal found 12/3$309
This Kiwi.com deal was found by Cheapflights users on 12/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/188:39 amORD - SJC
1 stop7h 37mAlaska Airlines
Mon 1/197:00 amSJC - ORD
1 stop29h 29mAlaska Airlines
Deal found 12/3$311
This Kiwi.com deal was found by Cheapflights users on 12/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:01 pmORD - SJC
2 stops45h 31mFrontier
Thu 1/811:27 amSJC - ORD
1 stop8h 05mFrontier
Deal found 12/2$314
This Southwest deal was found by Cheapflights users on 12/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:45 amMDW - SJC
1 stop7h 30mSouthwest
Wed 1/73:00 pmSJC - MDW
1 stop5h 40mSouthwest
Deal found 12/2$379
This Delta deal was found by Cheapflights users on 12/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/181:50 pmMDW - SJC
1 stop8h 46mDelta
Thu 1/810:45 pmSJC - MDW
1 stop9h 42mDelta
Deal found 12/3$397

Find flight deals from Chicago to San Jose

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to San Jose (SJC). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 4, 2025.

Most accurate provider

Gotogate
3 stars

Most trusted provider

Gotogate
3 stars

Round-trip from

$251
(KAYAK)

One-way from

$60
(Kiwi.com)

Popular in

July

Cheapest in

February

Average price

$397

Good round-trip deal

$417 or less

Good one-way deal

$268 or less
Provider with most accurate pricing for Chicago (CHI)-San Jose flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-San Jose flights.
Search Deals
From Chicago (CHI) to San Jose
Search Deals
One-way flight from Chicago (CHI) to San Jose
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to San Jose.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to San Jose.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to San Jose that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 4, 2025.
Use the filters below to find and compare flights from Chicago to San Jose that are best for you.

Fly from

Chicago

Fly to

San Jose

Route

Depart

Return

Price

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Wed 1/7

2:15 pm-7:35 pm

1 stop7h 20m

San Jose

Wed 1/14

11:20 am-10:35 pm

2 stops9h 15m

$267

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 3/5

6:00 am-12:36 pm

1 stop8h 36m

San Jose

Tue 3/10

10:45 pm-9:55 am

1 stop9h 10m

$268

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 3/5

9:50 am-5:38 pm

2 stops9h 48m

San Jose

Mon 3/9

10:45 pm-9:55 am

1 stop9h 10m

$276

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Wed 3/11

3:07 pm-10:56 pm

1 stop9h 49m

San Jose

Sun 3/15

7:00 am-11:59 pm

1 stop14h 59m

$278

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Sat 1/10

8:00 am-2:42 pm

1 stop8h 42m

San Jose

Thu 1/15

6:15 am-5:10 pm

1 stop8h 55m

$279

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Tue 1/6

7:30 am-1:30 pm

1 stop8h 00m

San Jose

Fri 1/16

6:20 am-3:19 pm

1 stop6h 59m

$288

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Mon 1/19

5:30 am-12:56 pm

1 stop9h 26m

San Jose

Sun 1/25

2:25 pm-11:53 pm

1 stop7h 28m

$288

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Sat 1/10

7:20 am-12:24 pm

1 stop7h 04m

San Jose

Fri 1/16

2:25 pm-11:53 pm

1 stop7h 28m

$288

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Fri 1/9

6:45 am-12:56 pm

1 stop8h 11m

San Jose

Sun 1/11

8:05 pm-8:52 am

2 stops10h 47m

$293

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Sun 1/11

11:05 am-10:12 pm

2 stops13h 07m

San Jose

Fri 1/16

9:15 am-9:05 pm

2 stops9h 50m

$298

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

Showing 1-10 of 41 results
1
2
3
...
5

Compare providers for flights from Chicago to San Jose

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to San Jose in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
GotogatePrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-San Jose, California flights, users find the pricing of Gotogate to be most consistent on Cheapflights vs. Gotogate Users can find the same prices on Chicago-San Jose, California flight deals on Cheapflights vs. Gotogate >95% of the time. Price accuracy is based on data collected from Chicago-San Jose, California flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-San Jose, California flights, Cheapflights users trust Gotogate the most. Gotogate has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-San Jose, California flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to San Jose

Have a flexible travel schedule? Discover the best time to fly to San Jose from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to San Jose

How far ahead should I book a flight from Chicago to San Jose, California?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to San Jose. Price data was last updated on November 28, 2025.

Booking 2 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to San Jose, California. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to San Jose, California?

Currently, October is the cheapest month in which you can book a flight from Chicago to San Jose, California (average of $80). Flying from Chicago to San Jose, California in November is currently the most expensive (average of $205). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to SJC?

Find hourly flight availability from Chicago to San Jose. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 4, 2025.

One of the essential ways to save on airfare from Chicago to San Jose, California is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 34% on airfare.

What is the cheapest day to fly from Chicago to San Jose, California?

Use this chart to determine the cheapest time to fly round-trip from Chicago to San Jose. Price data was last updated on November 29, 2025.

Travelers seeking maximum savings on their Chicago to San Jose, California flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

What’s the top layover airport for flights from Chicago to San Jose, California?

Share of 1-stop round-trip flights from Chicago to San Jose, California chosen by Cheapflights users in the past 12 months, using the same layover each way.

Denver (DEN) – chosen by Cheapflights users on 67% of 1-stop itineraries from Chicago to San Jose, California on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to San Jose, California?

Average round-trip fare for 1-stop flights from Chicago to San Jose, California, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of $170.

What’s the fastest layover option from Chicago to San Jose, California?

Shortest average travel time for 1-stop one-way flights from Chicago to San Jose, California, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 10h 23m.

Which airport typically offers the quickest layover for flights from Chicago to San Jose, California?

Average layover duration for 1-stop one-way flights from Chicago to San Jose, California, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Denver (DEN) offer the fastest connection on this route, with an average layover time of 2h 58m.

The best insider tips for Chicago to San Jose flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to San Jose trip
Airports
ORD

At ORD, Garrett Popcorn near gate B8 is a must-try snack before your flight.

Read more about ORDby Ramsey Qubein
MDW

For a quick check-in at MDW, use the indoor bridge to reach gates after security, reducing congestion and queues.

Read more about MDWby Ramsey Qubein
SJC

For a quick exit from SJC, use rideshare services with designated pick-up spots at all terminals.

Read more about SJCby Daniel Scheffler
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Daniel Scheffler

Daniel Scheffler

Expert on SJC

Daniel Scheffler

Daniel Scheffler

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more

Reviews of airlines servicing San Jose

Get insights into the airlines that provide service to San Jose. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San Jose. Reviews last updated December 4, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and United Airlines from Chicago to San Jose by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,402 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
11,402 reviews
Alaska Airlines
8.0
Very good
11,402 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,251 reviews
Alaska Airlines
8.0
Very good
11,402 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
9,066 reviews
Alaska Airlines
8.0
Very good
11,402 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Spirit Airlines
6.3
Okay
8,160 reviews
Alaska Airlines
8.0
Very good
11,402 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Frontier
5.8
Fair
3,091 reviews
Alaska Airlines
8.0
Very good
11,402 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

Related info for your journey

Find useful and relevant information for your journey from Chicago to San Jose. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to San Jose from Chicago?

    Located just 2.9 mi from the city center, San Jose is the airport most travelers will use when flying to San Jose from Chicago. Booking flights from Chicago to San Jose (SJC) should be relatively easy as there are 0 daily inbound flights from Chicago from 7 different airlines.

  • How long is the flight from Chicago to San Jose, California?

    A quick flight from Chicago to San Jose, California can take about 7h 20m. Southwest provides one of the quickest options available for as low as $267. Chicago and San Jose, California are separated by a distance of 1824 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago to San Jose, California round-trip?

    Frontier, at $80, was found to be the cheapest airline from Chicago to San Jose, California.Alternate airlines to your destination round-trip include Spirit Airlines and Alaska Airlines. Frontier is 80% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago to San Jose, California one-way?

    One-way options have recently been found by users for as low as $66 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $73 and Alaska Airlines from $89 one-way.

  • What are the cheapest flights from Chicago to San Jose, California?

    Looking for the cheapest flight from Chicago to San Jose, California? While on average our users pay $410, our data indicates the cheapest price to be $212. The most popular route (Chicago O'Hare Intl - San Jose), is priced around $127.

  • Can I find deals for flights from Chicago to San Jose that include hotel bookings?

    Yes. In addition to deals on Chicago to San Jose flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to San Jose?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to San Jose.

  • Can I find deals for business class flights from Chicago to San Jose?

    Yes. Cheapflights offers flight deals from Chicago to San Jose by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to San Jose, California?

    Currently, October is the cheapest month in which you can book a flight from Chicago to San Jose, California (average of $80). Flying from Chicago to San Jose, California in November is currently the most expensive (average of $205). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to San Jose

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Las Vegas flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to San Francisco flights
Midway to Las Vegas flights
O'Hare Intl to San Diego flights
O'Hare Intl to Santa Ana flights
Midway to Los Angeles flights
O'Hare Intl to Ontario flights
St. Louis to Las Vegas flights
Midway to San Francisco flights
O'Hare Intl to Palm Springs flights
Rockford to Las Vegas flights
O'Hare Intl to Reno flights
O'Hare Intl to Sacramento flights
St. Louis to Los Angeles flights
Midway to San Diego flights
O'Hare Intl to San Jose flights
O'Hare Intl to Burbank flights
O'Hare Intl to Oakland flights
St. Louis to San Francisco flights
Midway to Palm Springs flights
Midway to Santa Ana flights
St. Louis to San Diego flights
Midway to Ontario flights
St. Louis to Ontario flights
O'Hare Intl to Long Beach flights
Midway to Oakland flights
St. Louis to Santa Ana flights
Midway to San Jose flights
O'Hare Intl to Fresno flights
Midway to Reno flights
St. Louis to Burbank flights
O'Hare Intl to Santa Barbara flights
Moline to Las Vegas flights
Moline to Los Angeles flights
Midway to Sacramento flights
Peoria to San Diego flights
Bloomington to Las Vegas flights
Peoria to Las Vegas flights
St. Louis to San Jose flights
Midway to Burbank flights
St. Louis to Palm Springs flights
Midway to Long Beach flights
St. Louis to Long Beach flights
Peoria to Ontario flights
Peoria to Los Angeles flights
St. Louis to Sacramento flights
Peoria to Santa Ana flights
O'Hare Intl to Monterey flights
St. Louis to Oakland flights

Top 7 airlines flying from Chicago to San Jose

Discover the top 7 airlines that operate flights from Chicago to San Jose. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$80Average$244FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$142Average$215FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$262Average$361FlexibilityNo cancel feeOn-time75%
DeltaCheapest$265Average$391FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$333Average$482FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$339Average$501FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$352Average$620FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.