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San Jose

$73+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJC
Jun 4 — Jun 111
Thu 6/4
Thu 6/11
1 adult, Economy
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Find cheap flights from Chicago to San Jose with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Chicago to San Jose are usually found in January or November, booked 56 days in advance, depart on a Tuesday or Thursday and return on a Wednesday

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 May 5, 2026.

This CheapOair deal was found by Cheapflights users on 5/5. 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 8/289:07 pm
ORD
-
SJC
1 stop16h 55m
Frontier
Sun 8/3012:57 pm
SJC
-
ORD
1 stop15h 22m
Frontier
Deal found 5/5$280
This CheapOair deal was found by Cheapflights users on 5/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/228:46 pm
ORD
-
SJC
1 stop17h 13m
Frontier
Sun 5/2412:57 pm
SJC
-
ORD
1 stop15h 37m
Frontier
Deal found 5/1$281
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:50 pm
ORD
-
SJC
Nonstop4h 45m
United Airlines
Wed 6/31:10 pm
SJC
-
ORD
1 stop9h 35m
United Airlines
Deal found 4/30$283
This CheapOair deal was found by Cheapflights users on 4/30. 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.
Sat 5/237:59 pm
ORD
-
SJC
1 stop15h 46m
Alaska Airlines
Wed 5/2712:59 pm
SJC
-
ORD
1 stop22h 15m
Alaska Airlines
Deal found 4/30$285
This Delta deal was found by Cheapflights users on 5/5. 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.
Tue 6/25:41 pm
ORD
-
SJC
2 stops8h 00m
Delta
Wed 6/38:50 pm
SJC
-
ORD
2 stops9h 46m
Delta
Deal found 5/5$288
This Frontier deal was found by Cheapflights users on 5/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/117:20 am
ORD
-
SJC
1 stop7h 57m
Frontier
Mon 6/152:12 pm
SJC
-
ORD
1 stop12h 55m
Frontier
Deal found 5/2$290
This Southwest deal was found by Cheapflights users on 4/30. 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 6/98:55 pm
MDW
-
SJC
Nonstop4h 30m
Southwest
Tue 6/237:35 pm
SJC
-
MDW
1 stop7h 05m
Southwest
Deal found 4/30$292
This Expedia deal was found by Cheapflights users on 5/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:15 am
ORD
-
SJC
1 stop8h 02m
Multiple Airlines
Sat 8/2210:12 am
SJC
-
ORD
1 stop6h 51m
Multiple Airlines
Deal found 5/2$293
This Expedia deal was found by Cheapflights users on 5/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/167:15 am
ORD
-
SJC
1 stop8h 02m
Multiple Airlines
Tue 7/216:37 pm
SJC
-
ORD
1 stop8h 23m
Multiple Airlines
Deal found 5/4$299
This Expedia deal was found by Cheapflights users on 5/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:40 am
ORD
-
SJC
1 stop8h 00m
Alaska Airlines
Sat 6/67:06 am
SJC
-
ORD
1 stop9h 44m
Alaska Airlines
Deal found 5/4$300
This CheapOair deal was found by Cheapflights users on 5/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/228:46 pm
ORD
-
SJC
1 stop17h 13m
Frontier
Mon 5/2512:57 pm
SJC
-
ORD
1 stop15h 37m
Frontier
Deal found 5/1$301
This Southwest deal was found by Cheapflights users on 4/30. 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.
Wed 5/275:35 pm
MDW
-
SJC
1 stop6h 35m
Southwest
Wed 6/310:40 am
SJC
-
MDW
1 stop6h 55m
Southwest
Deal found 4/30$302

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 May 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$280
(CheapOair)

One-way from

$73
(Kiwi.com)

Popular in

February

Cheapest in

January

Average price

$417

Good round-trip deal

$384 or less

Good one-way deal

$203 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. 0% potential increase in price ($2 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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 May 5, 2026.
Use the filters below to find and compare flights from Chicago to San Jose that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Wed 5/27

7:50 pm-10:35 pm

Nonstop4h 45m

San Jose

Wed 6/3

1:10 pm-12:45 am

1 stop9h 35m

$283

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 5/27

5:35 pm-10:10 pm

1 stop6h 35m

San Jose

Wed 6/3

10:40 am-7:35 pm

1 stop6h 55m

$302

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Wed 5/27

9:00 am-2:13 pm

1 stop7h 13m

San Jose

Mon 6/1

2:00 pm-11:55 pm

1 stop7h 55m

$330

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 7/1

8:55 pm-11:25 pm

Nonstop4h 30m

San Jose

Sun 7/19

8:00 pm-4:40 am

1 stop6h 40m

$332

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Sun 6/7

7:37 pm-11:39 pm

1 stop6h 02m

San Jose

Tue 6/9

7:20 am-4:45 pm

1 stop7h 25m

$342

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 6/24

5:25 am-11:00 am

1 stop7h 35m

San Jose

Sat 7/11

7:55 pm-5:55 am

1 stop8h 00m

$342

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 6/3

1:22 pm-10:14 pm

2 stops10h 52m

San Jose

Mon 6/8

8:19 pm-8:37 am

2 stops10h 18m

$352

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Sun 5/24

9:23 am-5:02 pm

2 stops9h 39m

San Jose

Tue 5/26

10:00 pm-10:00 am

1 stop10h 00m

$367

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Wed 6/17

3:55 pm-11:39 pm

2 stops9h 44m

San Jose

Wed 6/24

9:54 am-9:25 pm

2 stops9h 31m

$372

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 6/17

8:55 pm-11:25 pm

Nonstop4h 30m

San Jose

Wed 6/24

10:55 pm-5:00 am

Nonstop4h 05m

$383

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/4

Showing 1-10 of 45 resultsSorted by cheapest first
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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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
GotogatePrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars

*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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-San Jose, California flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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?

Booking 55 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 March is currently the most expensive (average of $297). 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 May 5, 2026.

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 18% on airfare.

How much does it cost to fly round-trip from Chicago to San Jose, California?

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.

San Diego (SAN) – chosen by Cheapflights users on 50% 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.

Las Vegas (LAS) is the most affordable 1-stop option, with an average round-trip price of $299.

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 San Diego (SAN) have the shortest average one-way travel time for 1-stop routes: 7h 02m.

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 San Diego (SAN) offer the fastest connection on this route, with an average layover time of 2h 28m.

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
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

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 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 May 5, 2026.
Get a feel of what it's like to fly with Alaska Airlines,Southwest, andUnited 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
7.9
Good
12,329 reviews

Food

7.1

Crew

8.5

Overall

7.9

Comfort

7.8

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.
Alaska Airlines
7.9
Good
12,329 reviews
Alaska Airlines
7.9
Good
12,329 reviews

Food

7.1

Crew

8.5

Overall

7.9

Comfort

7.8

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.
Southwest
7.9
Good
4,305 reviews
Alaska Airlines
7.9
Good
12,329 reviews

Food

7.1

Crew

8.5

Overall

7.9

Comfort

7.8

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.
United Airlines
7.4
Good
9,683 reviews
Alaska Airlines
7.9
Good
12,329 reviews

Food

7.1

Crew

8.5

Overall

7.9

Comfort

7.8

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.
Frontier
5.6
Fair
2,965 reviews
Alaska Airlines
7.9
Good
12,329 reviews

Food

7.1

Crew

8.5

Overall

7.9

Comfort

7.8

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.

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 2 daily inbound flights from Chicago from 5 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 4h 45m. United Airlines provides one of the quickest options available for as low as $283. 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?

    Delta, at $189, was found to be the cheapest airline from Chicago to San Jose, California.Alternate airlines to your destination round-trip include Alaska Airlines and Southwest. Delta is 57% 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 $80 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $88 and Alaska Airlines from $98 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 $513, our data indicates the cheapest price to be $132. The most popular route (Chicago O'Hare Intl - San Jose), is priced around $257.

  • 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 March is currently the most expensive (average of $297). 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

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Alternative routes for Chicago to San Jose

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Chicago to San Jose

Discover the top 5 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 May 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$189Average$384FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$232Average$342FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$332Average$485FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$337Average$481FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$406Average$620FlexibilityNo cancel feeOn-time71%

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