HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
San Jose

$140+ Cheap flights from Chicago (CHI) to San Jose (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 5/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJC
May 6 — May 131
Tue 5/6
Tue 5/13
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 October or August, booked 58 days in advance, depart on a Wednesday or Thursday and return on a Tuesday

Cheap 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 1, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$242
(Flightnetwork)

One-way from

$140
(Booking.com)

Popular in

June

Cheapest in

October

Average price

$421

Good round-trip deal

$371 or less

Good one-way deal

$175 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 ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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

Find 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 1, 2025.

This Flightnetwork deal was found by Cheapflights users on 4/29. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1510:00 amORD - SJC
2 stops15h 29mSpirit Airlines
Tue 5/274:28 pmSJC - ORD
1 stop10h 57mSpirit Airlines
Deal found 4/29$242
This Expedia deal was found by Cheapflights users on 4/29. 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 5/2811:50 amORD - SJC
1 stop13h 39mMultiple Airlines
Sat 5/316:00 pmSJC - ORD
1 stop9h 40mMultiple Airlines
Deal found 4/29$245
This Frontier deal was found by Cheapflights users on 4/29. 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.
Fri 6/66:25 amMDW - SJC
1 stop9h 15mFrontier
Sun 6/812:13 pmSJC - MDW
1 stop6h 40mFrontier
Deal found 4/29$258
This Frontier deal was found by Cheapflights users on 4/29. 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 6/56:00 amORD - SJC
1 stop7h 18mFrontier
Sun 6/812:13 pmSJC - ORD
1 stop9h 46mFrontier
Deal found 4/29$258
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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 6/48:00 amORD - SJC
1 stop8h 51mAlaska Airlines
Tue 6/1012:25 pmSJC - ORD
1 stop7h 58mAlaska Airlines
Deal found 4/29$296
This Delta deal was found by Cheapflights users on 4/29. 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 6/101:47 pmMDW - SJC
1 stop8h 46mDelta
Tue 6/1710:25 pmSJC - MDW
1 stop9h 16mDelta
Deal found 4/29$299
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Tue 5/277:59 pmORD - SJC
Nonstop4h 40mUnited Airlines
Tue 6/36:35 amSJC - ORD
Nonstop4h 22mUnited Airlines
Deal found 4/29$311
This Delta deal was found by Cheapflights users on 4/29. 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 6/37:15 amORD - SJC
1 stop8h 30mDelta
Wed 6/117:18 amSJC - ORD
1 stop8h 02mDelta
Deal found 4/29$315
This Southwest deal was found by Cheapflights users on 4/29. 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 6/48:35 amMDW - SJC
1 stop6h 50mSouthwest
Wed 6/116:35 amSJC - MDW
Nonstop4h 10mSouthwest
Deal found 4/29$321
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/243:35 pmORD - SJC
1 stop9h 11mAmerican Airlines
Thu 7/37:09 pmSJC - ORD
1 stop8h 54mAmerican Airlines
Deal found 4/30$331
This Southwest deal was found by Cheapflights users on 4/29. 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.
Sat 6/284:00 pmORD - SJC
1 stop8h 10mSouthwest
Wed 7/210:40 amSJC - ORD
2 stops9h 40mSouthwest
Deal found 4/29$397
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/114:27 pmMDW - SJC
3 stops33h 07mMultiple Airlines
Wed 6/186:00 amSJC - MDW
3 stops35h 19mMultiple Airlines
Deal found 4/30$551

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 1, 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

Thu 5/15

10:00 am-11:29 pm

2 stops15h 29m

San Jose

Tue 5/27

4:28 pm-5:25 am

1 stop10h 57m

$242

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Wed 5/28

11:50 am-11:29 pm

1 stop13h 39m

San Jose

Sat 5/31

6:00 pm-5:40 am

1 stop9h 40m

$245

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Fri 6/6

6:25 am-1:40 pm

1 stop9h 15m

San Jose

Sun 6/8

12:13 pm-8:53 pm

1 stop6h 40m

$258

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Thu 6/5

6:00 am-11:18 am

1 stop7h 18m

San Jose

Sun 6/8

12:13 pm-11:59 pm

1 stop9h 46m

$258

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Wed 6/4

8:00 am-6:59 pm

1 stop12h 59m

San Jose

Tue 6/10

2:53 pm-11:56 pm

1 stop7h 03m

$296

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Tue 6/10

1:47 pm-8:33 pm

1 stop8h 46m

San Jose

Tue 6/17

10:25 pm-9:41 am

1 stop9h 16m

$299

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Tue 5/27

7:59 pm-10:39 pm

Nonstop4h 40m

San Jose

Tue 6/3

6:35 am-12:57 pm

Nonstop4h 22m

$311

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Tue 6/3

7:15 am-1:45 pm

1 stop8h 30m

San Jose

Wed 6/11

7:18 am-5:20 pm

1 stop8h 02m

$315

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 6/4

8:35 am-1:25 pm

1 stop6h 50m

San Jose

Wed 6/11

6:35 am-12:45 pm

Nonstop4h 10m

$321

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Tue 6/24

3:35 pm-10:46 pm

1 stop9h 11m

San Jose

Thu 7/3

7:09 pm-6:03 am

1 stop8h 54m

$331

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 25 results
1
2
3

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*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust 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 flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Chicago-San Jose flight deals on Cheapflights vs. CheapOair >95% of the time. Price accuracy is based on data collected from Chicago-San Jose flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-San Jose flights, Cheapflights users trust CheapOair the most. CheapOair 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 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?

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 April 25, 2025.

The price you pay for your flight from Chicago to San Jose may vary depending on when you book. For the best chance of a lower fare, look to book 58 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, September is the cheapest month in which you can book a flight from Chicago to San Jose (average of $255). Flying from Chicago to San Jose in June is currently the most expensive (average of $357). 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 1, 2025.

One of the essential ways to save on airfare from Chicago to San Jose 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 13% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Chicago to San Jose. Price data was last updated on March 30, 2025.

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

Rainfall in San Jose by month

Plan your trip to San Jose by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in San Jose ranges from 0.0 - 3.1 inches per month. January is typically the wettest month, when rainfall can reach 3.1 in. July is typically the driest time to visit San Jose when rainfall is around 0.0 in.

Temperature in San Jose by month

Plan your trip to San Jose by taking into account the average temperature totals by month.

If weather is an important factor for your trip to San Jose, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 50.0 F).

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 1, 2025.
See what other customers who have flown with Alaska Airlines, Southwest and Delta from Chicago to San Jose have to say. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Food

7.1

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,968 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Food

7.1

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,294 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Food

7.1

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Food

7.1

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,408 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Food

7.1

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Food

7.1

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 3 daily inbound flights from Chicago from 7 different airlines.

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

    According to our current data, Spirit Airlines ($242), Frontier ($258), and Alaska Airlines ($296) offers the cheapest pricing from Chicago to San Jose. Spirit Airlines is priced at 40% lower than the current average price of a flight leaving 3 months from now.

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

    The cheapest airlines for a one-way flight from Chicago to San Jose are Spirit Airlines ($140), Frontier ($143), and Alaska Airlines ($147).

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

    Looking for the cheapest flight from Chicago to San Jose? While on average our users pay $364, our data indicates the cheapest price to be $155. The most popular route (Chicago O'Hare Intl - San Jose), is priced around $112.

  • 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?

    Currently, September is the cheapest month in which you can book a flight from Chicago to San Jose (average of $255). Flying from Chicago to San Jose in June is currently the most expensive (average of $357). 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
Midway to Las Vegas flights
O'Hare Intl to San Diego flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Ontario flights
Midway to San Francisco flights
O'Hare Intl to Santa Ana flights
St. Louis to Las Vegas flights
O'Hare Intl to Burbank flights
Midway to Los Angeles flights
O'Hare Intl to Oakland flights
O'Hare Intl to Sacramento flights
O'Hare Intl to San Jose flights
Midway to San Diego flights
St. Louis to Los Angeles flights
O'Hare Intl to Palm Springs flights
O'Hare Intl to Reno flights
Midway to Ontario flights
St. Louis to San Diego flights
St. Louis to San Francisco flights
Rockford to Las Vegas flights
O'Hare Intl to Fresno flights
Midway to Sacramento flights
Midway to Santa Ana flights
St. Louis to Sacramento flights
Midway to San Jose flights
O'Hare Intl to Long Beach flights
St. Louis to Santa Ana flights
St. Louis to Ontario flights
Midway to Oakland flights
O'Hare Intl to Medford flights
Midway to Reno flights
Midway to Palm Springs flights
O'Hare Intl to Santa Barbara flights
Midway to Long Beach flights
Midway to Burbank flights
Moline to Las Vegas flights
Moline to Los Angeles flights
St. Louis to Burbank flights
St. Louis to Reno flights
Peoria to San Diego flights
Moline to Ontario flights
St. Louis to San Jose flights
St. Louis to Long Beach flights
Peoria to Las Vegas flights
O'Hare Intl to Santa Rosa flights
Midway to Fresno flights
Decatur to Las Vegas flights
Peoria to Santa Ana 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$248FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$133Average$242FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$140Average$314FlexibilityNo cancel feeOn-time75%
DeltaCheapest$274Average$382FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$297Average$495FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$353Average$473FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$370Average$472FlexibilityNo 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.