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$68+ 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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — CHI
feb. 28 — mar. 71
sáb. 2/28
sáb. 3/7
1 adult, Economy
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Cheapflights Tip: The best prices from San Jose to Chicago are usually found in February or March, booked 43 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 enero 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
lun. 3/98:20 pm
SJC
-
ORD
1 stop7h 48m
Frontier
mié. 3/114:28 pm
ORD
-
SJC
2 stops27h 39m
Frontier
Deal found 1/28$166
This Expedia deal was found by Cheapflights users on 1/27. 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.
jue. 2/2610:34 am
SJC
-
ORD
1 stop28h 52m
Multiple Airlines
mar. 3/33:07 pm
ORD
-
SJC
1 stop9h 49m
Multiple Airlines
Deal found 1/27$208
This Expedia deal was found by Cheapflights users on 1/27. 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.
jue. 2/2610:34 am
SJC
-
ORD
1 stop28h 52m
Multiple Airlines
mié. 3/48:20 am
ORD
-
SJC
1 stop12h 17m
Multiple Airlines
Deal found 1/27$217
This Expedia deal was found by Cheapflights users on 1/27. 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.
jue. 2/2610:34 am
SJC
-
ORD
1 stop28h 52m
Multiple Airlines
lun. 3/23:07 pm
ORD
-
SJC
1 stop23h 01m
Multiple Airlines
Deal found 1/27$227
This CheapOair deal was found by Cheapflights users on 1/27. 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.
mié. 2/258:05 pm
SJC
-
ORD
1 stop16h 53m
Alaska Airlines
mar. 3/33:07 pm
ORD
-
SJC
1 stop9h 49m
Alaska Airlines
Deal found 1/27$237
This CheapOair deal was found by Cheapflights users on 1/28. 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.
mié. 4/297:43 pm
SJC
-
ORD
1 stop8h 57m
Alaska Airlines
mié. 5/63:52 pm
ORD
-
SJC
1 stop19h 52m
Alaska Airlines
Deal found 1/28$247
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
lun. 3/22:53 pm
SJC
-
ORD
1 stop7h 06m
Hawaiian Airlines
mar. 3/108:20 am
ORD
-
SJC
1 stop7h 53m
Hawaiian Airlines
Deal found 1/28$253
This CheapOair deal was found by Cheapflights users on 1/27. 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.
sáb. 2/2811:38 am
SJC
-
ORD
1 stop23h 33m
Alaska Airlines
sáb. 3/75:29 pm
ORD
-
SJC
1 stop16h 53m
Alaska Airlines
Deal found 1/27$257
This CheapOair deal was found by Cheapflights users on 1/28. 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.
mié. 4/297:43 pm
SJC
-
ORD
1 stop8h 57m
Alaska Airlines
lun. 5/117:59 pm
ORD
-
SJC
1 stop18h 04m
Alaska Airlines
Deal found 1/28$260
This CheapOair deal was found by Cheapflights users on 1/28. 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.
mié. 4/2910:21 am
SJC
-
ORD
2 stops11h 38m
Alaska Airlines
mar. 5/53:52 pm
ORD
-
SJC
1 stop19h 52m
Alaska Airlines
Deal found 1/28$265
This Southwest deal was found by Cheapflights users on 1/27. 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.
mar. 3/107:15 am
SJC
-
MDW
1 stop7h 25m
Southwest
mar. 3/1710:30 am
MDW
-
SJC
Nonstop4h 40m
Southwest
Deal found 1/27$307
This Delta deal was found by Cheapflights users on 1/27. 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.
mar. 3/108:35 pm
SJC
-
MDW
2 stops10h 15m
Delta
mar. 3/176:00 am
MDW
-
SJC
1 stop8h 08m
Delta
Deal found 1/27$322

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 enero 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$166
(Kiwi.com)

One-way from

$68
(Trip.com)

Popular in

December

Cheapest in

February

Average price

$432

Good round-trip deal

$404 or less

Good one-way deal

$205 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
Highest demand for flights based on searches. 5% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 enero 29, 2026.
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 - ORD

SJCORD

San Jose

jue. 2/26

10:34 am-5:26 pm

1 stop28h 52m

Chicago O'Hare Intl

dom. 3/1

3:07 pm-2:16 pm

1 stop25h 09m

$277

San JoseChicago

SJC - ORD

SJCORD

San Jose

sáb. 5/16

7:00 am-6:46 pm

1 stop9h 46m

Chicago O'Hare Intl

lun. 5/18

7:59 pm-12:07 pm

1 stop18h 08m

$290

San JoseChicago

SJC - ORD

SJCORD

San Jose

mié. 2/18

12:45 pm-11:59 pm

1 stop9h 14m

Chicago O'Hare Intl

jue. 2/19

3:07 pm-10:56 pm

1 stop9h 49m

$303

San JoseChicago

SJC - ORD

SJCORD

San Jose

lun. 2/23

7:14 pm-11:59 pm

1 stop26h 45m

Chicago O'Hare Intl

jue. 2/26

8:20 am-6:37 pm

1 stop12h 17m

$313

San JoseChicago

SJC - ORD

SJCORD

San Jose

sáb. 3/21

11:40 am-11:52 pm

1 stop10h 12m

Chicago O'Hare Intl

mié. 3/25

2:20 pm-10:18 pm

1 stop9h 58m

$320

San JoseChicago

SJC - MDW

SJCMDW

San Jose

lun. 3/9

10:55 pm-5:00 am

Nonstop4h 05m

Chicago Midway

mié. 3/11

10:30 am-1:10 pm

Nonstop4h 40m

$323

San JoseChicago

SJC - ORD

SJCORD

San Jose

jue. 5/7

6:43 am-7:03 pm

1 stop10h 20m

Chicago O'Hare Intl

dom. 5/10

7:59 pm-12:03 pm

1 stop18h 04m

$333

San JoseChicago

SJC - ORD

SJCORD

San Jose

mar. 4/7

8:39 pm-2:21 pm

1 stop15h 42m

Chicago O'Hare Intl

lun. 4/13

7:59 pm-6:45 pm

1 stop24h 46m

$333

San JoseChicago

SJC - ORD

SJCORD

San Jose

sáb. 5/16

8:00 am-11:59 pm

2 stops13h 59m

Chicago O'Hare Intl

mar. 5/19

3:43 pm-11:37 pm

1 stop9h 54m

$335

San JoseChicago

SJC - MDW

SJCMDW

San Jose

sáb. 4/4

7:55 pm-5:40 am

1 stop7h 45m

Chicago Midway

mar. 4/7

6:45 am-11:30 am

1 stop6h 45m

$343

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 49 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
GotogatePrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Jose, California-Chicago flight deals on Cheapflights vs. FlightHub >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 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 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 January 23, 2026.

The best time to book flights from San Jose, California to Chicago is 43 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, October is the cheapest month in which you can book a flight from San Jose, California to Chicago (average of $125). Flying from San Jose, California to Chicago in December is currently the most expensive (average of $233). 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 enero 29, 2026.

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 26% on your trip compared to booking a flight in the evening.

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
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

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 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 enero 29, 2026.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta 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
11,807 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,807 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Southwest
8.0
Very good
4,267 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Delta
7.9
Good
8,127 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,215 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Frontier
5.7
Fair
3,056 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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 $323, Alaska Airlines can have you in Chicago from San Jose, California in 4h 05m. The distance from San Jose, California to Chicago is about 1832 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 $62, 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 85% 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 $86 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 $975, our data indicates the cheapest price to be $193. The most popular route (San Jose - Chicago O'Hare Intl), is priced around $227.

  • 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, October is the cheapest month in which you can book a flight from San Jose, California to Chicago (average of $125). Flying from San Jose, California to Chicago in December is currently the most expensive (average of $233). 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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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 enero 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$62Average$244FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$125Average$239FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$170Average$315FlexibilityNo cancel feeOn-time75%
DeltaCheapest$208Average$407FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$253Average$410FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$297Average$519FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$330Average$501FlexibilityNo cancel feeOn-time63%

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