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$137+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — CHI
May 9 — May 161
Sat 5/9
Sat 5/16
1 adult, Economy
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Cheapflights Tip: The best prices from San Jose to Chicago are usually found in September or February, booked 75 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

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 April 9, 2026.

This Southwest deal was found by Cheapflights users on 4/7. 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.
Tue 5/510:55 pm
SJC
-
MDW
Nonstop4h 05m
Southwest
Wed 5/276:05 pm
MDW
-
SJC
1 stop6h 55m
Southwest
Deal found 4/7$267
This Southwest deal was found by Cheapflights users on 4/6. 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 5/612:45 pm
SJC
-
ORD
2 stops9h 10m
Southwest
Wed 5/137:45 am
ORD
-
SJC
2 stops8h 00m
Southwest
Deal found 4/6$267
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 5/712:57 pm
SJC
-
ORD
1 stop15h 42m
Frontier
Sat 5/98:56 pm
ORD
-
SJC
2 stops42h 21m
Frontier
Deal found 4/4$268
This CheapOair deal was found by Cheapflights users on 4/6. 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.
Fri 5/2212:57 pm
SJC
-
ORD
1 stop15h 37m
Frontier
Thu 5/288:46 pm
ORD
-
SJC
1 stop17h 13m
Frontier
Deal found 4/6$270
This Southwest deal was found by Cheapflights users on 4/7. 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 5/2710:55 pm
SJC
-
MDW
Nonstop4h 05m
Southwest
Sat 5/305:20 pm
MDW
-
SJC
Nonstop4h 35m
Southwest
Deal found 4/7$271
This Delta deal was found by Cheapflights users on 4/6. 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 5/272:51 pm
SJC
-
ORD
1 stop7h 06m
Delta
Sat 5/307:45 am
ORD
-
SJC
1 stop7h 03m
Delta
Deal found 4/6$271
This Southwest deal was found by Cheapflights users on 4/7. 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.
Tue 5/510:55 pm
SJC
-
MDW
Nonstop4h 05m
Southwest
Tue 5/127:30 am
MDW
-
SJC
2 stops8h 15m
Southwest
Deal found 4/7$272
This American Airlines deal was found by Cheapflights users on 4/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/44:18 pm
SJC
-
ORD
1 stop6h 14m
American Airlines
Tue 5/127:04 am
ORD
-
SJC
1 stop7h 02m
American Airlines
Deal found 4/8$272
This Expedia deal was found by Cheapflights users on 4/7. 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 4/3012:44 pm
SJC
-
ORD
1 stop8h 59m
Multiple Airlines
Sun 5/37:21 pm
ORD
-
SJC
1 stop26h 06m
Multiple Airlines
Deal found 4/7$273
This Southwest deal was found by Cheapflights users on 4/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/301:30 pm
SJC
-
MDW
1 stop6h 05m
Southwest
Mon 5/48:25 pm
MDW
-
SJC
Nonstop4h 35m
Southwest
Deal found 4/8$275
This United Airlines deal was found by Cheapflights users on 4/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3012:56 pm
SJC
-
ORD
1 stop9h 49m
United Airlines
Mon 5/48:02 pm
ORD
-
SJC
Nonstop4h 56m
United Airlines
Deal found 4/8$275
This Delta deal was found by Cheapflights users on 4/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:50 pm
SJC
-
MDW
2 stops9h 52m
Delta
Wed 6/31:59 pm
MDW
-
SJC
1 stop8h 39m
Delta
Deal found 4/8$276

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 April 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$267
(Southwest)

One-way from

$137
(CheapOair)

Popular in

March

Cheapest in

September

Average price

$470

Good round-trip deal

$386 or less

Good one-way deal

$228 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. 4% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 9, 2026.
Use the filters below to find and compare flights from San Jose to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 8/18

10:20 pm-10:24 am

2 stops10h 04m

Chicago O'Hare Intl

Wed 8/26

9:30 am-6:45 pm

2 stops11h 15m

$267

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 5/7

9:35 pm-5:25 am

1 stop5h 50m

Chicago Midway

Thu 5/14

6:15 am-10:30 am

1 stop6h 15m

$280

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 5/7

9:10 am-5:55 pm

1 stop6h 45m

Chicago Midway

Mon 5/11

6:15 am-10:30 am

1 stop6h 15m

$280

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 5/7

1:00 pm-10:55 pm

1 stop7h 55m

Chicago O'Hare Intl

Mon 5/11

6:15 pm-10:25 pm

1 stop6h 10m

$285

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 5/7

12:44 pm-11:43 pm

1 stop8h 59m

Chicago O'Hare Intl

Mon 5/11

7:59 pm-9:44 am

1 stop15h 45m

$300

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 5/7

8:50 pm-8:42 am

2 stops9h 52m

Chicago Midway

Mon 5/11

1:22 pm-10:14 pm

2 stops10h 52m

$315

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 5/28

10:55 pm-5:00 am

Nonstop4h 05m

Chicago Midway

Tue 6/2

10:20 am-12:55 pm

Nonstop4h 35m

$324

San JoseChicago

SJC - ORD

SJCORD

San Jose

Wed 5/20

1:40 pm-9:50 pm

1 stop6h 10m

Chicago O'Hare Intl

Wed 5/27

2:11 pm-6:20 pm

1 stop6h 09m

$328

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 5/27

10:55 pm-5:00 am

Nonstop4h 05m

Chicago Midway

Fri 5/29

10:05 am-2:15 pm

1 stop6h 10m

$328

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sat 5/23

7:55 pm-5:00 am

1 stop7h 05m

Chicago Midway

Sat 5/30

5:10 am-10:10 am

1 stop7h 00m

$330

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

Showing 1-10 of 51 resultsSorted by cheapest first
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6

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
MytripPrice 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 April 9, 2026.

The best time to book flights from San Jose, California to Chicago is 75 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 April 9, 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 24% on your trip compared to booking a flight in the evening.

Weekly flight availability from San Jose, California 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 April 9, 2026.

The most flights from SJC to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

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
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 April 9, 2026.
Peruse reviews from past customers who have flown with Southwest,Alaska Airlines, andDelta 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.
Southwest
8.0
Very good
4,337 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,337 reviews
Southwest
8.0
Very good
4,337 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Alaska Airlines
7.9
Good
12,197 reviews
Southwest
8.0
Very good
4,337 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Delta
7.9
Good
8,392 reviews
Southwest
8.0
Very good
4,337 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
United Airlines
7.4
Good
9,555 reviews
Southwest
8.0
Very good
4,337 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Spirit Airlines
6.3
Okay
8,606 reviews
Southwest
8.0
Very good
4,337 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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 2 daily outbound flights to Chicago from 7 different airlines.

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

    For as low as $280, Delta can have you in Chicago from San Jose, California in 5h 50m. 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?

    Spirit Airlines, at $121, was found to be the cheapest airline from San Jose, California to Chicago.Alternate airlines to your destination round-trip include Frontier and Alaska Airlines. Users have found that Spirit Airlines is 73% 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 $88 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 most reliable airlines from San Jose, California to Chicago?

    Before booking your flight to Chicago from San Jose, California, check out the most reliable airlines to get you to your destination on time: American Airlines (100%), Qatar Airways (100%), United Airlines( 94%).

  • 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 $837, our data indicates the cheapest price to be $203. The most popular route (San Jose - Chicago O'Hare Intl), is priced around $209.

  • 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 April 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$121Average$239FlexibilityNo cancel feeOn-time65%
FrontierCheapest$131Average$294FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$170Average$315FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$200Average$424FlexibilityNo cancel feeOn-time71%
DeltaCheapest$208Average$417FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$280Average$525FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$330Average$515FlexibilityNo cancel feeOn-time63%

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