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$91+ Cheap flights from San Jose, CA (SJC) to Chicago (CHI)

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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — CHI
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Cheapflights Tip: The best prices from San Jose to Chicago are usually found in January or March, booked 26 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

Cheap flight deals from San Jose to Chicago

Cheapest flights from San Jose to Chicago
Explore the most affordable flight options available from San Jose to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:43 pmSJC - ORD
1 stop8h 22mMultiple Airlines
Tue 12/304:47 pmORD - SJC
2 stops47h 45mMultiple Airlines
Deal found 12/14$431
This Alaska Airlines deal was found by Cheapflights users on 12/15. 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.
Thu 12/255:13 pmSJC - ORD
1 stop9h 49mAlaska Airlines
Mon 1/58:58 pmORD - SJC
1 stop27h 41mAlaska Airlines
Deal found 12/15$454
This Delta deal was found by Cheapflights users on 12/16. 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.
Sun 12/286:20 amSJC - MDW
1 stop8h 59mDelta
Fri 1/99:32 amMDW - SJC
2 stops10h 08mDelta
Deal found 12/16$490
This Delta deal was found by Cheapflights users on 12/14. 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.
Sun 12/2810:55 pmSJC - ORD
1 stop7h 52mDelta
Mon 1/57:30 amORD - SJC
1 stop29h 27mDelta
Deal found 12/14$490
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:43 pmSJC - ORD
1 stop8h 22mMultiple Airlines
Thu 1/17:00 amORD - SJC
2 stops13h 48mMultiple Airlines
Deal found 12/14$500
This Delta deal was found by Cheapflights users on 12/14. 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.
Sun 12/2810:55 pmSJC - MDW
1 stop8h 10mDelta
Mon 1/51:49 pmMDW - SJC
1 stop9h 39mDelta
Deal found 12/14$502
This Alaska Airlines deal was found by Cheapflights users on 12/14. 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.
Tue 12/305:57 pmSJC - ORD
1 stop28h 02mAlaska Airlines
Mon 1/58:58 pmORD - SJC
1 stop27h 41mAlaska Airlines
Deal found 12/14$502
This Alaska Airlines deal was found by Cheapflights users on 12/15. 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 12/242:53 pmSJC - ORD
1 stop21h 44mAlaska Airlines
Mon 1/58:58 pmORD - SJC
1 stop27h 41mAlaska Airlines
Deal found 12/15$503
This Delta deal was found by Cheapflights users on 12/14. 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.
Mon 12/295:40 pmSJC - MDW
2 stops13h 09mDelta
Mon 1/51:49 pmMDW - SJC
1 stop9h 39mDelta
Deal found 12/14$507
This Alaska Airlines deal was found by Cheapflights users on 12/13. 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.
Mon 12/227:00 amSJC - ORD
1 stop11h 02mAlaska Airlines
Mon 1/126:06 pmORD - SJC
1 stop25h 02mAlaska Airlines
Deal found 12/13$507
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:43 pmSJC - ORD
1 stop8h 22mMultiple Airlines
Wed 12/319:34 pmORD - SJC
2 stops23h 14mMultiple Airlines
Deal found 12/14$509
This Southwest deal was found by Cheapflights users on 12/13. 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 12/316:30 amSJC - MDW
Nonstop4h 10mSouthwest
Sun 1/45:15 amMDW - SJC
1 stop6h 25mSouthwest
Deal found 12/13$518

Find flight deals from San Jose to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from San Jose (SJC) to Chicago (CHI). 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 December 16, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$353
(Alaska Airlines)

One-way from

$91
(Priceline)

Popular in

December

Cheapest in

January

Average price

$517

Good round-trip deal

$453 or less

Good one-way deal

$150 or less
Provider with most accurate pricing for San Jose-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Jose-Chicago (CHI) flights.
Search Deals
From San Jose to Chicago (CHI)
Search Deals
One-way flight from San Jose to Chicago (CHI)
Search Deals
High demand for flights, 3% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from San Jose to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from San Jose to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Jose to Chicago 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 December 16, 2025.
Use the filters below to find and compare flights from San Jose to Chicago that are best for you.

Fly from

San Jose

Fly to

Chicago

Route

Depart

Return

Price

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 1/7

6:25 pm-8:52 am

2 stops12h 27m

Chicago Midway

Wed 1/14

6:45 am-12:56 pm

1 stop8h 11m

$360

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 1/20

10:45 pm-9:53 am

1 stop9h 08m

Chicago Midway

Tue 1/27

6:00 am-5:40 pm

2 stops13h 40m

$360

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 2/13

9:15 am-8:44 pm

2 stops9h 29m

Chicago O'Hare Intl

Wed 2/18

2:20 pm-10:05 pm

1 stop9h 45m

$360

San JoseChicago

SJC - ORD

SJCORD

San Jose

Wed 5/27

12:25 pm-10:23 pm

1 stop7h 58m

Chicago O'Hare Intl

Sat 5/30

9:20 am-2:21 pm

1 stop7h 01m

$367

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 4/30

7:00 am-6:55 pm

1 stop9h 55m

Chicago O'Hare Intl

Sun 5/3

7:55 pm-9:48 am

1 stop15h 53m

$367

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 5/12

7:28 pm-1:54 pm

1 stop16h 26m

Chicago O'Hare Intl

Sat 5/16

2:54 pm-10:32 pm

1 stop9h 38m

$367

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 2/13

7:00 am-11:59 pm

1 stop14h 59m

Chicago O'Hare Intl

Wed 2/18

3:07 pm-10:56 pm

1 stop9h 49m

$371

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 6/4

7:00 am-6:55 pm

1 stop9h 55m

Chicago O'Hare Intl

Mon 6/8

7:51 pm-9:12 am

1 stop15h 21m

$379

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 1/8

7:45 am-10:07 pm

2 stops12h 22m

Chicago Midway

Fri 1/9

1:49 pm-9:28 pm

1 stop9h 39m

$380

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 1/8

10:45 pm-10:27 am

1 stop9h 42m

Chicago Midway

Thu 1/15

9:32 am-5:40 pm

2 stops10h 08m

$380

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 47 results
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Compare providers for flights from San Jose to Chicago

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 San Jose to Chicago in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
GotogatePrice Accuracy3 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 San Jose, California-Chicago flights, users find the pricing of Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on San Jose, California-Chicago flight deals on Cheapflights vs. Mytrip >95% of the time. Price accuracy is based on data collected from San Jose, California-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San Jose, California-Chicago 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 San Jose, California-Chicago 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 San Jose to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from San Jose 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 San Jose to Chicago

How far ahead should I book a flight from San Jose, California to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from San Jose to Chicago. Price data was last updated on December 12, 2025.

The best time to book flights from San Jose, California to Chicago is 26 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, December is the cheapest month in which you can book a flight from San Jose, California to Chicago (average of $107). Flying from San Jose, California to Chicago in November is currently the most expensive (average of $210). 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 SJC to CHI?

Find hourly flight availability from San Jose to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 16, 2025.

A simple way to save on the total cost of your ticket is to fly from San Jose, California to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 42% on your trip compared to booking a flight in the evening.

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

The best insider tips for San Jose to Chicago 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 San Jose to Chicago trip
Airports
SJC

SJC offers free Wi-Fi throughout the airport, making it easy to stay connected before your flight.

Read more about SJCBy Daniel Scheffler
ORD

For a quick city connection, take the “L” train from ORD to downtown Chicago, avoiding traffic delays.

Read more about ORDBy Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

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

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated December 16, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and United Airlines from San Jose to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,465 reviews

Food

7.1

Comfort

7.8

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Alaska Airlines
8.0
Very good
11,465 reviews
Alaska Airlines
8.0
Very good
11,465 reviews

Food

7.1

Comfort

7.8

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Southwest
7.9
Good
4,250 reviews
Alaska Airlines
8.0
Very good
11,465 reviews

Food

7.1

Comfort

7.8

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
United Airlines
7.4
Good
9,094 reviews
Alaska Airlines
8.0
Very good
11,465 reviews

Food

7.1

Comfort

7.8

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Spirit Airlines
6.3
Okay
8,188 reviews
Alaska Airlines
8.0
Very good
11,465 reviews

Food

7.1

Comfort

7.8

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Frontier
5.8
Fair
3,082 reviews
Alaska Airlines
8.0
Very good
11,465 reviews

Food

7.1

Comfort

7.8

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

Related info for your journey

Find useful and relevant information for your journey from San Jose to Chicago. 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 from for flights from San Jose to Chicago?

    Located just 2.9 mi from the city center, San Jose is the airport most travelers will use when flying to Chicago from San Jose. Booking flights from San Jose (SJC) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 7 different airlines.

  • How long is the flight from San Jose, California to Chicago?

    For as low as $367, Delta can have you in Chicago from San Jose, California in 7h 58m. The distance from San Jose, California to Chicago is about 1824 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Frontier, at $65, was found to be the cheapest airline from San Jose, California to Chicago.Alternate airlines to your destination round-trip include Spirit Airlines and Alaska Airlines. Users have found that Frontier is 84% cheaper than the other options available to this destination.

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

    $60 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and Alaska Airlines, with prices starting from $65 and $98, respectively.

  • What are the most popular routes from San Jose, California to Chicago?

    While some choose either San Jose - Chicago Midway or San Jose - Chicago Greater Rockford, San Jose - Chicago O'Hare Intl is the most popular route from San Jose, California to Chicago.

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

    Looking for the cheapest flight from San Jose, California to Chicago? While on average our users pay $969, our data indicates the cheapest price to be $148. The most popular route (San Jose - Chicago O'Hare Intl), is priced around $183.

  • Can I find deals for flights from San Jose to Chicago that include hotel bookings?

    Yes. In addition to deals on San Jose to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Jose to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Jose to Chicago.

  • Can I find deals for business class flights from San Jose to Chicago?

    Yes. Cheapflights offers flight deals from San Jose to Chicago 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 San Jose, California to Chicago?

    Currently, December is the cheapest month in which you can book a flight from San Jose, California to Chicago (average of $107). Flying from San Jose, California to Chicago in November is currently the most expensive (average of $210). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for San Jose to Chicago

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Top 7 airlines flying from San Jose to Chicago

Discover the top 7 airlines that operate flights from San Jose to Chicago. 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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$98Average$268FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$125Average$231FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$170Average$315FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$200Average$353FlexibilityNo cancel feeOn-time71%
DeltaCheapest$256Average$399FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$287Average$495FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$331Average$504FlexibilityNo cancel feeOn-time63%

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