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San Jose

$141+ 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 6/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJC
Apr 27 — May 41
Sun 4/27
Sun 5/4
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 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 April 22, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$249
(FlightHub)

One-way from

$141
(FlightHub)

Popular in

June

Cheapest in

October

Average price

$407

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.
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Provider most trusted by Cheapflights users for Chicago (CHI)-San Jose flights.
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From Chicago (CHI) to San Jose
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One-way flight from Chicago (CHI) to San Jose
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Highest demand for flights based on searches. 6% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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.
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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 April 22, 2025.

This Mytrip deal was found by Cheapflights users on 4/22. 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.
Sun 5/118:37 amORD - SJC
2 stops27h 28mSpirit Airlines
Tue 5/136:00 amSJC - ORD
2 stops22h 42mSpirit Airlines
Deal found 4/22$247
This FlightHub deal was found by Cheapflights users on 4/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/99:02 pmORD - SJC
1 stop15h 03mMultiple Airlines
Mon 5/127:41 pmSJC - ORD
1 stop7h 29mMultiple Airlines
Deal found 4/22$255
This CheapOair deal was found by Cheapflights users on 4/21. 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.
Sun 5/48:03 pmMDW - SJC
1 stop17h 17mFrontier
Thu 5/87:41 pmSJC - MDW
1 stop17h 07mFrontier
Deal found 4/21$281
This CheapOair deal was found by Cheapflights users on 4/22. 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.
Thu 5/18:14 pmORD - SJC
1 stop24h 27mFrontier
Mon 5/57:41 pmSJC - ORD
1 stop7h 29mFrontier
Deal found 4/22$281
This Hawaiian Airlines deal was found by Cheapflights users on 4/22. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1412:00 pmORD - SJC
1 stop10h 04mHawaiian Airlines
Sat 5/246:00 pmSJC - ORD
1 stop9h 40mHawaiian Airlines
Deal found 4/22$314
This Alaska Airlines deal was found by Cheapflights users on 4/21. 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 5/216:00 amORD - SJC
2 stops15h 17mAlaska Airlines
Sat 5/243:50 pmSJC - ORD
1 stop11h 50mAlaska Airlines
Deal found 4/21$320
This Delta deal was found by Cheapflights users on 4/22. 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.
Sat 6/77:15 amORD - SJC
1 stop8h 30mDelta
Wed 6/117:00 amSJC - ORD
2 stops11h 27mDelta
Deal found 4/22$328
This Delta deal was found by Cheapflights users on 4/21. 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.
Wed 6/41:55 pmMDW - SJC
1 stop8h 36mDelta
Wed 6/1112:17 pmSJC - MDW
1 stop7h 28mDelta
Deal found 4/21$331
This United Airlines deal was found by Cheapflights users on 4/21. 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.
Thu 8/287:55 pmORD - SJC
Nonstop4h 45mUnited Airlines
Sun 9/76:30 amSJC - ORD
Nonstop4h 25mUnited Airlines
Deal found 4/21$331
This Southwest deal was found by Cheapflights users on 4/21. 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 8/28:15 pmMDW - SJC
Nonstop4h 35mSouthwest
Sat 8/98:35 amSJC - MDW
Nonstop4h 10mSouthwest
Deal found 4/21$351
This Southwest deal was found by Cheapflights users on 4/22. 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.
Thu 6/192:50 pmORD - SJC
2 stops7h 35mSouthwest
Thu 6/268:45 amSJC - ORD
2 stops12h 55mSouthwest
Deal found 4/22$382
This Mytrip deal was found by Cheapflights users on 4/21. 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.
Mon 6/169:12 amMDW - SJC
2 stops26h 52mMultiple Airlines
Thu 6/191:33 pmSJC - MDW
3 stops22h 30mMultiple Airlines
Deal found 4/21$485

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 April 22, 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

Sun 5/11

8:37 am-10:05 am

2 stops27h 28m

San Jose

Tue 5/13

6:00 am-6:42 am

2 stops22h 42m

$247

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Fri 5/9

9:02 pm-10:05 am

1 stop15h 03m

San Jose

Mon 5/12

7:41 pm-5:10 am

1 stop7h 29m

$255

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Sun 5/4

8:03 pm-11:20 am

1 stop17h 17m

San Jose

Thu 5/8

7:41 pm-2:48 pm

1 stop17h 07m

$281

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Thu 5/1

8:14 pm-6:41 pm

1 stop24h 27m

San Jose

Mon 5/5

7:41 pm-5:10 am

1 stop7h 29m

$281

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Wed 5/14

12:00 pm-8:04 pm

1 stop10h 04m

San Jose

Sat 5/24

6:00 pm-5:40 am

1 stop9h 40m

$314

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Wed 5/21

6:00 am-7:17 pm

2 stops15h 17m

San Jose

Sat 5/24

3:50 pm-5:40 am

1 stop11h 50m

$320

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Sat 6/7

7:15 am-1:45 pm

1 stop8h 30m

San Jose

Wed 6/11

7:00 am-8:27 pm

2 stops11h 27m

$328

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 6/4

1:55 pm-8:31 pm

1 stop8h 36m

San Jose

Wed 6/11

12:17 pm-9:45 pm

1 stop7h 28m

$331

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Sat 8/2

8:15 pm-10:50 pm

Nonstop4h 35m

San Jose

Sat 8/9

8:35 am-2:45 pm

Nonstop4h 10m

$351

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Fri 5/23

7:59 pm-10:39 pm

Nonstop4h 40m

San Jose

Sun 5/25

6:35 am-12:57 pm

Nonstop4h 22m

$372

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 24 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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy1 starTrust 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 Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Chicago-San Jose flight deals on Cheapflights vs. Mytrip >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 Mytrip the most. Mytrip 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 18, 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 $362). 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 April 22, 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 April 22, 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
9,911 reviews

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,911 reviews
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Hawaiian Airlines
7.9
Good
2,392 reviews
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,683 reviews
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 ($249), Frontier ($251), and Alaska Airlines ($314) offers the cheapest pricing from Chicago to San Jose. Spirit Airlines is priced at 38% 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 ($141), Frontier ($149), and Southwest ($156).

  • 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 $169. The most popular route (Chicago O'Hare Intl - San Jose), is priced around $190.

  • 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 $362). 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 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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$248FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$133Average$243FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$140Average$314FlexibilityNo cancel feeOn-time75%
DeltaCheapest$274Average$366FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$302Average$496FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$353Average$477FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$370Average$472FlexibilityNo cancel feeOn-time71%

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