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$50+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJC
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
1 adult, Economy
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The best prices from Chicago to San Jose are usually found in October or April, booked 22 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

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 February 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$143
(Booking.com)

One-way from

$50
(FlightHub)

Popular in

March

Cheapest in

October

Average price

$434

Good round-trip deal

$443 or less

Good one-way deal

$200 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. 3% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 22, 2025.

This Booking.com deal was found by Cheapflights users on 2/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/126:45 amORD - SJC
1 stop10h 18mMultiple Airlines
Mon 3/247:54 pmSJC - ORD
1 stop8h 48mMultiple Airlines
Deal found 2/21$143
This CheapOair deal was found by Cheapflights users on 2/22. 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.
Mon 3/2410:27 pmORD - SJC
1 stop17h 07mSpirit Airlines
Mon 3/312:29 pmSJC - ORD
1 stop20h 24mSpirit Airlines
Deal found 2/22$145
This eDestinos deal was found by Cheapflights users on 2/22. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/88:50 pmMDW - SJC
2 stops20h 09mFrontier
Tue 4/157:28 pmSJC - MDW
1 stop7h 55mFrontier
Deal found 2/22$150
This Flightnetwork deal was found by Cheapflights users on 2/21. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/126:45 amORD - SJC
1 stop10h 18mFrontier
Thu 3/201:00 pmSJC - ORD
1 stop14h 04mFrontier
Deal found 2/21$158
This Delta deal was found by Cheapflights users on 2/21. 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.
Fri 4/257:50 amORD - SJC
1 stop8h 10mDelta
Tue 4/296:29 amSJC - ORD
1 stop9h 01mDelta
Deal found 2/21$183
This Delta deal was found by Cheapflights users on 2/22. 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.
Tue 4/89:23 amMDW - SJC
2 stops10h 22mDelta
Tue 4/156:15 amSJC - MDW
1 stop6h 07mDelta
Deal found 2/22$268
This Trip.com deal was found by Cheapflights users on 2/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/28:44 pmMDW - SJC
2 stops19h 39mMultiple Airlines
Fri 3/74:03 pmSJC - MDW
1 stop6h 14mMultiple Airlines
Deal found 2/21$295
This Alaska Airlines deal was found by Cheapflights users on 2/22. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/147:45 amORD - SJC
1 stop18h 11mAlaska Airlines
Mon 3/244:52 pmSJC - ORD
2 stops11h 07mAlaska Airlines
Deal found 2/22$338
This Southwest deal was found by Cheapflights users on 2/20. 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.
Mon 3/109:35 amMDW - SJC
Nonstop4h 45mSouthwest
Tue 3/118:35 amSJC - MDW
Nonstop4h 10mSouthwest
Deal found 2/20$351

Find flights from Chicago to San Jose within your budget

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 February 22, 2025.

Fly from

Chicago

Fly to

San Jose

Route

Depart

Return

Price

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Wed 3/12

6:45 am-3:03 pm

1 stop10h 18m

San Jose

Mon 3/24

7:54 pm-6:42 am

1 stop8h 48m

$143

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Mon 3/24

10:27 pm-1:34 pm

1 stop17h 07m

San Jose

Mon 3/31

2:29 pm-12:53 pm

1 stop20h 24m

$145

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Tue 4/8

8:50 pm-2:59 pm

2 stops20h 09m

San Jose

Tue 4/15

7:28 pm-5:23 am

1 stop7h 55m

$150

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Wed 3/12

6:45 am-3:03 pm

1 stop10h 18m

San Jose

Thu 3/20

1:00 pm-5:04 am

1 stop14h 04m

$158

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Fri 4/25

7:50 am-2:00 pm

1 stop8h 10m

San Jose

Sun 4/27

6:29 am-5:30 pm

1 stop9h 01m

$183

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Tue 4/8

9:23 am-5:45 pm

2 stops10h 22m

San Jose

Tue 4/15

6:15 am-2:22 pm

1 stop6h 07m

$268

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Fri 3/14

7:45 am-11:56 pm

1 stop18h 11m

San Jose

Mon 3/24

4:52 pm-5:59 am

2 stops11h 07m

$338

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Mon 4/7

6:45 am-10:51 pm

2 stops18h 06m

San Jose

Mon 4/14

4:52 pm-9:11 am

2 stops14h 19m

$349

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Mon 3/10

9:35 am-12:20 pm

Nonstop4h 45m

San Jose

Tue 3/11

8:35 am-2:45 pm

Nonstop4h 10m

$351

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Tue 4/15

11:53 am-6:37 pm

1 stop8h 44m

$50

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

Showing 1-10 of 20 results
1
2

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy1 starTrust 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-San Jose flight deals on Cheapflights vs. FlightHub >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 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 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.

Travel insights for flights from Chicago to San Jose

Get recent, data-driven insights about flights from Chicago to San Jose including ideal travel times, pricing trends, and more.

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 February 14, 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 22 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 $371). 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 February 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 at noon tend to be the most expensive. A flight in the morning could potentially save you up to 4% 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 February 16, 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. Tuesday at noon 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 February 22, 2025.
See what other customers who have flown with Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Comfort

8.1

Food

7.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Southwest
8.1
Very good
4,396 reviews
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Comfort

8.1

Food

7.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Alaska Airlines
8.0
Very good
9,702 reviews
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Comfort

8.1

Food

7.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Comfort

8.1

Food

7.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Hawaiian Airlines
7.9
Good
2,314 reviews
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Comfort

8.1

Food

7.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Comfort

8.1

Food

7.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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 4 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 ($145), Frontier ($150), and Delta ($183) offers the cheapest pricing from Chicago to San Jose. Spirit Airlines is priced at 64% 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 ($50), Frontier ($71), and Delta ($97).

  • 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 $416, our data indicates the cheapest price to be $175. 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 $371). 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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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 February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$215FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$246FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$140Average$376FlexibilityNo cancel feeOn-time75%
DeltaCheapest$237Average$361FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$288Average$502FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$376Average$487FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$393Average$557FlexibilityNo cancel feeOn-time71%
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