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$103+ 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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJC
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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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 July 3, 2025.

Round-trip from

$247
(Frontier)

One-way from

$103
(FlightHub)

Popular in

June

Cheapest in

October

Average price

$442

Good round-trip deal

$396 or less

Good one-way deal

$249 or less
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. 8% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Chicago (CHI) to San Jose.
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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 July 3, 2025.

This Frontier deal was found by Cheapflights users on 7/2. 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.
Fri 9/196:00 amORD - SJC
1 stop7h 30mFrontier
Mon 9/226:50 pmSJC - ORD
2 stops13h 50mFrontier
Deal found 7/2$247
This Mytrip deal was found by Cheapflights users on 7/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/66:40 amORD - SJC
2 stops19h 14mSpirit Airlines
Sun 8/104:22 pmSJC - ORD
2 stops11h 03mSpirit Airlines
Deal found 7/3$248
This Delta deal was found by Cheapflights users on 7/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/164:25 pmMDW - SJC
1 stop7h 53mDelta
Sat 8/2310:25 pmSJC - MDW
1 stop8h 10mDelta
Deal found 7/2$257
This Delta deal was found by Cheapflights users on 7/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/207:55 amORD - SJC
1 stop6h 28mDelta
Sat 9/206:11 pmSJC - ORD
2 stops12h 14mDelta
Deal found 7/2$262
This CheapOair deal was found by Cheapflights users on 6/30. 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.
Thu 9/181:53 pmMDW - SJC
2 stops30h 02mFrontier
Sun 9/212:09 pmSJC - MDW
1 stop23h 44mFrontier
Deal found 6/30$264
This Justfly.com deal was found by Cheapflights users on 7/1. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/75:40 amORD - SJC
1 stop7h 42mMultiple Airlines
Sun 8/104:22 pmSJC - ORD
1 stop11h 41mMultiple Airlines
Deal found 7/1$264
This Southwest deal was found by Cheapflights users on 7/2. 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 10/215:25 pmMDW - SJC
Nonstop4h 30mSouthwest
Tue 10/287:30 amSJC - MDW
Nonstop4h 05mSouthwest
Deal found 7/2$297

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 July 3, 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

Fri 9/19

6:00 am-11:30 am

1 stop7h 30m

San Jose

Mon 9/22

6:50 pm-10:40 am

2 stops13h 50m

$247

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Wed 8/6

6:40 am-11:54 pm

2 stops19h 14m

San Jose

Sun 8/10

4:22 pm-5:25 am

2 stops11h 03m

$248

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Sat 8/16

4:25 pm-10:18 pm

1 stop7h 53m

San Jose

Sat 8/23

10:25 pm-8:35 am

1 stop8h 10m

$257

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Sat 9/20

7:55 am-12:23 pm

1 stop6h 28m

San Jose

Sat 9/20

6:11 pm-8:25 am

2 stops12h 14m

$262

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Thu 8/7

5:40 am-11:22 am

1 stop7h 42m

San Jose

Sun 8/10

4:22 pm-6:03 am

1 stop11h 41m

$264

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 9/18

1:53 pm-5:55 pm

2 stops30h 02m

San Jose

Sun 9/21

2:09 pm-3:53 pm

1 stop23h 44m

$264

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Tue 10/21

5:25 pm-7:55 pm

Nonstop4h 30m

San Jose

Tue 10/28

7:30 am-1:35 pm

Nonstop4h 05m

$297

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Sun 8/10

3:18 pm-11:54 pm

1 stop10h 36m

$103

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Mon 8/18

6:00 am-1:17 pm

1 stop9h 17m

$106

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Thu 7/24

5:40 am-11:22 am

1 stop7h 42m

$120

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 17 results
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The best insider tips for Chicago to San Jose flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
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

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 June 27, 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 $358). 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 July 3, 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 afternoon tend to be the most expensive. A flight at noon could potentially save you up to 15% 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 June 29, 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.

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 July 3, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Delta 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
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

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
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

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
4,266 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

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
7,982 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

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
8,861 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Spirit Airlines
6.3
Okay
8,086 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

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 6 different airlines.

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

    According to our current data, Frontier ($247), Spirit Airlines ($248), and Delta ($257) offers the cheapest pricing from Chicago to San Jose. Frontier is priced at 39% 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 ($103), Frontier ($125), and Delta ($129).

  • 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 $552, our data indicates the cheapest price to be $155. The most popular route (Chicago O'Hare Intl - San Jose), is priced around $149.

  • 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 $358). 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 6 airlines flying from Chicago to San Jose

Discover the top 6 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$248FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$127Average$249FlexibilityNo cancel feeOn-time65%
DeltaCheapest$277Average$391FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$317Average$504FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$370Average$472FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$376Average$482FlexibilityNo cancel feeOn-time63%

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