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$108+ 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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 81 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 July 3, 2025.

Round-trip from

$254
(Cheapflightsfares)

One-way from

$108
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$413

Good round-trip deal

$387 or less

Good one-way deal

$185 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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High demand for flights, 9% potential price rise
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Cheapest flight prices on average. 0% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/276:30 amSJC - ORD
1 stop5h 43mSpirit Airlines
Sat 8/97:49 pmORD - SJC
1 stop6h 05mSpirit Airlines
Deal found 7/2$254
This FlightHub deal was found by Cheapflights users on 7/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/246:30 amSJC - ORD
1 stop5h 43mMultiple Airlines
Sun 7/279:56 pmORD - SJC
1 stop17h 21mMultiple Airlines
Deal found 7/2$256
This Delta deal was found by Cheapflights users on 7/2. 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.
Wed 8/276:25 amSJC - MDW
1 stop9h 12mDelta
Tue 9/21:08 pmMDW - SJC
1 stop9h 34mDelta
Deal found 7/2$257
This American Airlines deal was found by Cheapflights users on 7/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/56:00 amSJC - ORD
1 stop7h 05mAmerican Airlines
Tue 8/54:39 pmORD - SJC
1 stop8h 20mAmerican Airlines
Deal found 7/2$258
This Expedia deal was found by Cheapflights users on 7/2. 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.
Thu 7/2412:18 pmSJC - MDW
1 stop6h 36mFrontier
Thu 8/78:38 pmMDW - SJC
2 stops18h 39mFrontier
Deal found 7/2$262
This Priceline deal was found by Cheapflights users on 7/1. 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.
Thu 7/1012:18 pmSJC - ORD
1 stop9h 52mFrontier
Sun 7/135:40 amORD - SJC
1 stop7h 42mFrontier
Deal found 7/1$270
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/226:00 pmSJC - ORD
2 stops12h 24mDelta
Sun 8/245:45 amORD - SJC
2 stops9h 15mDelta
Deal found 7/3$285
This Mytrip deal was found by Cheapflights users on 6/30. 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 9/188:15 amSJC - RFD
1 stop8h 37mMultiple Airlines
Mon 9/2210:37 amRFD - SJC
2 stops13h 12mMultiple Airlines
Deal found 6/30$287
This Southwest deal was found by Cheapflights users on 7/3. 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 9/2511:30 amSJC - MDW
1 stop6h 10mSouthwest
Mon 9/297:55 pmMDW - SJC
Nonstop4h 30mSouthwest
Deal found 7/3$303

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 July 3, 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

Sun 7/27

6:30 am-2:13 pm

1 stop5h 43m

Chicago O'Hare Intl

Sat 8/9

7:49 pm-11:54 pm

1 stop6h 05m

$254

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 7/24

6:30 am-2:13 pm

1 stop5h 43m

Chicago O'Hare Intl

Sun 7/27

9:56 pm-1:17 pm

1 stop17h 21m

$256

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 8/27

6:25 am-5:37 pm

1 stop9h 12m

Chicago Midway

Tue 9/2

1:08 pm-8:42 pm

1 stop9h 34m

$257

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 8/5

6:00 am-3:05 pm

1 stop7h 05m

Chicago O'Hare Intl

Tue 8/5

4:39 pm-10:59 pm

1 stop8h 20m

$258

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 7/24

12:18 pm-8:54 pm

1 stop6h 36m

Chicago Midway

Thu 8/7

8:38 pm-1:17 pm

2 stops18h 39m

$262

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 8/22

6:00 pm-8:24 am

2 stops12h 24m

Chicago O'Hare Intl

Sun 8/24

5:45 am-1:00 pm

2 stops9h 15m

$285

San JoseChicago

SJC - RFD

SJCRFD

San Jose

Thu 9/18

8:15 am-6:52 pm

1 stop8h 37m

Chicago Greater Rockford

Mon 9/22

10:37 am-9:49 pm

2 stops13h 12m

$287

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 8/21

12:22 pm-12:32 am

1 stop10h 10m

Chicago O'Hare Intl

Fri 8/22

6:00 am-5:32 pm

2 stops13h 32m

$289

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 9/25

11:30 am-7:40 pm

1 stop6h 10m

Chicago Midway

Mon 9/29

7:55 pm-10:25 pm

Nonstop4h 30m

$303

San JoseChicago

SJC - ORD

SJCORD

San Jose

Wed 8/20

6:00 am-5:40 am

2 stops21h 40m

$108

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 22 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 June 27, 2025.

The best time to book flights from San Jose to Chicago is 81 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 July 3, 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 29, 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.

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

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 July 3, 2025.
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
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

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

Boarding

8.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

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
4,266 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

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
7,982 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.8
Good
2,545 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

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
8,861 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

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 4 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 $254. Other airlines that can offer you cheap pricing are Delta, from $257, and American Airlines, from $258. You may be able to fly from San Jose to Chicago for 37% 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 $108 on Spirit Airlines. Other airlines that offer cheap prices include Hawaiian Airlines from $112 and Frontier from $113 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 $1,619, our data indicates the cheapest price to be $175. The most popular route (San Jose - Chicago O'Hare Intl), is priced around $167.

  • 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

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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$98Average$259FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$108Average$253FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$170Average$243FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$200Average$494FlexibilityNo cancel feeOn-time71%
DeltaCheapest$236Average$352FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$287Average$495FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$358Average$491FlexibilityNo cancel feeOn-time63%

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