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$90+ Cheap flights from San Jose (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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 15 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

Cheap 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 September 11, 2025.

Round-trip from

$207
(United Airlines)

One-way from

$90
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$381

Good round-trip deal

$301 or less

Good one-way deal

$169 or less
From San Jose to Chicago (CHI)
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One-way flight from San Jose to Chicago (CHI)
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Highest demand for flights based on searches. 9% potential increase in price ($44 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 September 2025
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Price to beat on a round-trip flight from San Jose to Chicago (CHI).
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Price to beat on a one-way flight from San Jose to Chicago (CHI).
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Find 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 September 11, 2025.

This United Airlines deal was found by Cheapflights users on 9/11. 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.
Sat 10/258:45 amSJC - ORD
1 stop9h 10mUnited Airlines
Thu 10/307:35 pmORD - SJC
Nonstop4h 53mUnited Airlines
Deal found 9/11$207
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1012:35 pmSJC - ORD
1 stop10h 24mFrontier
Fri 10/176:50 amORD - SJC
1 stop6h 42mFrontier
Deal found 9/10$210
This Alaska Airlines deal was found by Cheapflights users on 9/10. 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 10/207:54 pmSJC - ORD
1 stop21h 05mAlaska Airlines
Wed 11/59:20 amORD - SJC
1 stop7h 03mAlaska Airlines
Deal found 9/10$211
This Alaska Airlines deal was found by Cheapflights users on 9/10. 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 10/81:30 pmSJC - ORD
1 stop8h 29mAlaska Airlines
Tue 10/147:59 pmORD - SJC
1 stop15h 58mAlaska Airlines
Deal found 9/10$212
This Southwest deal was found by Cheapflights users on 9/11. 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 11/58:00 amSJC - MDW
1 stop7h 00mSouthwest
Sun 11/97:50 amMDW - SJC
Nonstop4h 45mSouthwest
Deal found 9/11$213
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Tue 11/1110:25 amSJC - ORD
1 stop7h 30mMultiple Airlines
Fri 11/146:00 amORD - SJC
1 stop7h 32mMultiple Airlines
Deal found 9/8$213
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 9/256:35 amSJC - ORD
1 stop12h 57mMultiple Airlines
Tue 9/306:44 pmORD - SJC
2 stops18h 01mMultiple Airlines
Deal found 9/11$214
This Southwest deal was found by Cheapflights users on 9/10. 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 10/257:20 amSJC - MDW
1 stop6h 55mSouthwest
Sat 11/14:10 pmMDW - SJC
Nonstop4h 30mSouthwest
Deal found 9/10$215
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Tue 9/3011:40 amSJC - ORD
2 stops21h 00mMultiple Airlines
Thu 10/25:35 amORD - SJC
1 stop9h 39mMultiple Airlines
Deal found 9/11$215
This Alaska Airlines deal was found by Cheapflights users on 9/9. 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 9/3012:52 pmSJC - ORD
1 stop7h 15mAlaska Airlines
Fri 10/31:01 pmORD - SJC
1 stop7h 59mAlaska Airlines
Deal found 9/9$216
This CheapOair deal was found by Cheapflights users on 9/10. 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 9/252:14 pmSJC - ORD
1 stop17h 23mFrontier
Mon 9/296:00 amORD - SJC
2 stops13h 45mFrontier
Deal found 9/10$217
This Frontier deal was found by Cheapflights users on 9/10. 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 11/712:27 pmSJC - ORD
1 stop9h 48mFrontier
Mon 11/106:00 amORD - SJC
1 stop7h 32mFrontier
Deal found 9/10$220

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 September 11, 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

Thu 11/27

6:35 am-12:45 pm

Nonstop4h 10m

Chicago Midway

Tue 12/2

9:35 am-3:00 pm

1 stop7h 25m

$213

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 10/14

3:55 pm-11:59 pm

1 stop6h 04m

Chicago O'Hare Intl

Thu 10/16

5:01 am-9:52 am

1 stop6h 51m

$217

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sun 10/19

6:35 am-12:45 pm

Nonstop4h 10m

Chicago Midway

Sat 10/25

2:15 pm-6:50 pm

1 stop6h 35m

$226

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 10/2

9:30 am-5:00 am

1 stop17h 30m

Chicago O'Hare Intl

Tue 10/7

7:59 pm-9:57 am

1 stop15h 58m

$228

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 10/30

12:38 pm-11:59 pm

1 stop9h 21m

Chicago O'Hare Intl

Tue 11/4

8:59 pm-12:01 pm

1 stop17h 02m

$233

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 11/11

10:25 am-11:59 pm

1 stop11h 34m

Chicago O'Hare Intl

Wed 11/12

9:20 am-2:23 pm

1 stop7h 03m

$242

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sun 10/19

6:35 am-12:45 pm

Nonstop4h 10m

Chicago Midway

Thu 10/23

5:45 am-10:30 am

1 stop6h 45m

$249

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 12/30

6:10 am-3:24 pm

1 stop7h 14m

Chicago O'Hare Intl

Tue 1/6

7:30 am-4:31 pm

2 stops11h 01m

$254

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 2/24

10:30 pm-9:56 am

1 stop9h 26m

Chicago Midway

Wed 2/25

2:00 pm-9:06 pm

1 stop9h 06m

$257

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 10/23

6:20 am-4:50 pm

1 stop8h 30m

Chicago O'Hare Intl

Sat 10/25

5:20 am-11:17 am

1 stop7h 57m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 50 results
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The best insider tips for San Jose to Chicago 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 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

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 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 August 29, 2025.

The best time to book flights from San Jose to Chicago is 15 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 to Chicago?

Currently, August is the cheapest month in which you can book a flight from San Jose to Chicago (average of $245). Flying from San Jose to Chicago in March is currently the most expensive (average of $321). 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 September 11, 2025.

A simple way to save on the total cost of your ticket is to fly from San Jose to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 34% on your trip compared to booking a flight in the evening.

What is the cheapest day to fly from San Jose to Chicago?

Use this chart to determine the cheapest time to fly round-trip from San Jose to Chicago. Price data was last updated on September 7, 2025.

Travelers seeking maximum savings on their San Jose to Chicago flight should consider departing on Monday afternoons when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from San Jose to Chicago

Explore weekly flight availability from San Jose to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 11, 2025.

The most flights from SJC to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

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 September 11, 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
10,000 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,248 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,937 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Spirit Airlines
6.3
Okay
8,023 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Frontier
5.8
Fair
3,177 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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 4 daily outbound flights to Chicago from 7 different airlines.

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

    Airlines like Southwest, United Airlines, and Alaska Airlines fly from San Jose to Chicago in about 4h 10m. The time it takes to get you to your destination can typically vary by up to 13h 20m. Airlines will cover a distance of 1832 mi. This flight may include one or multiple stops.

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

    Cheapflights users have booked flights from San Jose to Chicago round-trip from $98. Other airlines that can offer you cheap pricing are Spirit Airlines, from $140, and Alaska Airlines, from $155. You may be able to fly from San Jose to Chicago for 75% less than the average price by searching for these airlines.

  • What are the most popular routes from San Jose 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 to Chicago.

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

    Looking for the cheapest flight from San Jose to Chicago? While on average our users pay $460, our data indicates the cheapest price to be $175. The most popular route (San Jose - Chicago O'Hare Intl), is priced around $173.

  • 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 to Chicago?

    Currently, August is the cheapest month in which you can book a flight from San Jose to Chicago (average of $245). Flying from San Jose to Chicago in March is currently the most expensive (average of $321). 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?

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$98Average$259FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$140Average$232FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$155Average$217FlexibilityNo cancel feeOn-time75%
DeltaCheapest$236Average$358FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$253Average$353FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$311Average$527FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$331Average$498FlexibilityNo cancel feeOn-time63%

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