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$115+ 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 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from San Jose to Chicago are usually found in January or November, booked 61 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 June 12, 2025.

Round-trip from

$239
(Mytrip)

One-way from

$115
(Mytrip)

Popular in

June

Cheapest in

January

Average price

$456

Good round-trip deal

$389 or less

Good one-way deal

$207 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. 6% potential increase in price ($30 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 June 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 June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2411:01 amSJC - ORD
2 stops17h 50mSpirit Airlines
Tue 7/11:43 pmORD - SJC
2 stops22h 23mSpirit Airlines
Deal found 6/10$239
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/186:00 amSJC - RFD
1 stop10h 52mMultiple Airlines
Sun 9/218:37 pmRFD - SJC
1 stop14h 47mMultiple Airlines
Deal found 6/10$250
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/57:25 amSJC - ORD
1 stop7h 55mDelta
Tue 8/127:15 amORD - SJC
1 stop8h 34mDelta
Deal found 6/11$255
This KAYAK deal was found by Cheapflights users on 6/11. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1112:17 pmSJC - ORD
1 stop9h 36mFrontier
Sun 9/146:00 amORD - SJC
1 stop7h 32mFrontier
Deal found 6/11$295
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1112:17 pmSJC - MDW
1 stop8h 21mFrontier
Sun 9/147:56 pmMDW - SJC
1 stop17h 36mFrontier
Deal found 6/11$299
This Alaska Airlines deal was found by Cheapflights users on 6/11. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/228:00 amSJC - ORD
1 stop13h 59mAlaska Airlines
Sun 10/267:55 pmORD - SJC
1 stop18h 06mAlaska Airlines
Deal found 6/11$299
This Booking.com deal was found by Cheapflights users on 6/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/197:00 pmSJC - ORD
1 stop23h 56mMultiple Airlines
Tue 6/2410:15 pmORD - SJC
1 stop13h 51mMultiple Airlines
Deal found 6/10$316
This Delta deal was found by Cheapflights users on 6/12. 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 8/126:25 amSJC - MDW
1 stop9h 12mDelta
Wed 8/2012:43 pmMDW - SJC
1 stop9h 04mDelta
Deal found 6/12$319
This Trip.com deal was found by Cheapflights users on 6/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/227:00 pmSJC - MDW
1 stop17h 56mMultiple Airlines
Sun 6/297:40 amMDW - SJC
2 stops28h 26mMultiple Airlines
Deal found 6/11$320
This Southwest deal was found by Cheapflights users on 6/12. 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.
Thu 8/1411:30 amSJC - MDW
1 stop6h 10mSouthwest
Tue 8/1912:45 pmMDW - SJC
1 stop6h 35mSouthwest
Deal found 6/12$366
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Tue 9/26:30 amSJC - ORD
Nonstop4h 25mUnited Airlines
Fri 9/57:55 pmORD - SJC
Nonstop4h 45mUnited Airlines
Deal found 6/11$380

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 June 12, 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 - ORD

SJCORD

San Jose

Tue 6/24

11:01 am-6:51 am

2 stops17h 50m

Chicago O'Hare Intl

Tue 7/1

1:43 pm-10:06 am

2 stops22h 23m

$239

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 8/5

7:25 am-5:20 pm

1 stop7h 55m

Chicago O'Hare Intl

Tue 8/12

7:15 am-1:49 pm

1 stop8h 34m

$255

San JoseChicago

SJC - RFD

SJCRFD

San Jose

Wed 7/9

6:30 am-11:54 am

1 stop27h 24m

Chicago Greater Rockford

Sun 7/13

12:44 pm-3:27 pm

2 stops28h 43m

$258

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 6/19

7:00 pm-8:56 pm

1 stop23h 56m

Chicago O'Hare Intl

Thu 6/26

10:15 pm-10:06 am

1 stop13h 51m

$302

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 8/12

6:25 am-5:37 pm

1 stop9h 12m

Chicago Midway

Wed 8/20

12:43 pm-7:47 pm

1 stop9h 04m

$319

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sun 6/22

7:00 pm-2:56 pm

1 stop17h 56m

Chicago Midway

Sun 6/29

7:40 am-10:06 am

2 stops28h 26m

$320

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 7/1

6:00 am-2:14 pm

1 stop6h 14m

Chicago O'Hare Intl

Tue 7/1

3:52 pm-9:13 pm

1 stop7h 21m

$323

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 8/15

9:46 pm-12:07 pm

1 stop12h 21m

Chicago O'Hare Intl

Fri 8/22

7:00 am-9:00 pm

2 stops16h 00m

$324

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 9/4

12:17 pm-11:53 pm

1 stop9h 36m

Chicago O'Hare Intl

Mon 9/8

6:00 am-11:32 am

1 stop7h 32m

$337

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 6/26

7:00 pm-2:56 pm

1 stop17h 56m

Chicago Midway

Mon 6/30

6:25 am-1:23 pm

1 stop8h 58m

$343

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 25 results
1
2
3

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 June 9, 2025.

The best time to book flights from San Jose to Chicago is 61 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 June 12, 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 32% 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 June 8, 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 June 12, 2025.

The most flights from SJC to CHI are scheduled on a Wednesday (10 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta from San Jose to Chicago 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

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

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

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

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
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

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
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,494 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

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
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

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 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 6 daily outbound flights to Chicago from 7 different airlines.

  • 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 $239. Other airlines that can offer you cheap pricing are Delta, from $255, and Frontier, from $295. You may be able to fly from San Jose to Chicago for 40% less than the average price by searching for these airlines.

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

    One-way options have recently been found by users for as low as $115 on Spirit Airlines. Other airlines that offer cheap prices include Delta from $136 and Alaska Airlines from $138 one-way.

  • 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 $669, our data indicates the cheapest price to be $169. The most popular route (San Jose - Chicago O'Hare Intl), is priced around $172.

  • 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 San Jose?

Book flights to San Jose if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Alternative routes for San Jose to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$98Average$248FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$124Average$265FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$170Average$243FlexibilityNo cancel feeOn-time75%
DeltaCheapest$236Average$353FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$279Average$549FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$287Average$494FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$358Average$498FlexibilityNo cancel feeOn-time63%

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