Chicago

$144+ 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — CHI
Jun 21 — Jun 281
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Find cheap flights from San Jose to Chicago with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from San Jose to Chicago are usually found in February or September, booked 80 days in advance, depart on a Wednesday or Saturday and return on a Tuesday

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 May 22, 2026.

This Delta deal was found by Cheapflights users on 5/16. 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 8/266:00 am
SJC
-
MDW
2 stops10h 33m
Delta
Tue 9/16:00 am
MDW
-
SJC
1 stop7h 33m
Delta
Deal found 5/16$282
This Delta deal was found by Cheapflights users on 5/17. 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 6/97:00 am
SJC
-
ORD
2 stops12h 57m
Delta
Wed 7/16:30 am
ORD
-
SJC
1 stop7h 35m
Delta
Deal found 5/17$282
This Delta deal was found by Cheapflights users on 5/16. 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 9/27:00 am
SJC
-
MDW
2 stops12h 46m
Delta
Tue 9/86:00 am
MDW
-
SJC
2 stops12h 15m
Delta
Deal found 5/16$288
This Alaska Airlines deal was found by Cheapflights users on 5/18. 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 6/98:00 am
SJC
-
ORD
1 stop19h 00m
Alaska Airlines
Wed 6/106:20 am
ORD
-
SJC
1 stop7h 04m
Alaska Airlines
Deal found 5/18$292
This Expedia deal was found by Cheapflights users on 5/16. 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.
Sat 8/158:25 pm
SJC
-
ORD
1 stop7h 52m
Multiple Airlines
Tue 8/187:59 pm
ORD
-
SJC
1 stop15h 23m
Multiple Airlines
Deal found 5/16$293
This Gotogate deal was found by Cheapflights users on 5/17. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:25 pm
SJC
-
ORD
1 stop7h 52m
Frontier
Wed 8/199:07 pm
ORD
-
SJC
1 stop16h 55m
Frontier
Deal found 5/17$294
This Frontier deal was found by Cheapflights users on 5/18. 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.
Sat 8/12:12 pm
SJC
-
ORD
1 stop13h 16m
Frontier
Thu 8/137:15 am
ORD
-
SJC
1 stop8h 02m
Frontier
Deal found 5/18$298
This Expedia deal was found by Cheapflights users on 5/16. 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.
Sat 7/112:12 pm
SJC
-
ORD
1 stop13h 16m
Multiple Airlines
Tue 7/147:59 pm
ORD
-
SJC
1 stop15h 27m
Multiple Airlines
Deal found 5/16$299
This Southwest deal was found by Cheapflights users on 5/21. 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 7/2810:55 pm
SJC
-
MDW
Nonstop4h 05m
Southwest
Wed 8/58:30 pm
MDW
-
SJC
Nonstop4h 30m
Southwest
Deal found 5/21$302
This Frontier deal was found by Cheapflights users on 5/18. 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.
Mon 8/38:25 pm
SJC
-
ORD
1 stop7h 52m
Frontier
Sat 8/87:15 am
ORD
-
SJC
1 stop8h 02m
Frontier
Deal found 5/18$303
This SmartFares deal was found by Cheapflights users on 5/18. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/812:59 pm
SJC
-
ORD
1 stop8h 56m
Alaska Airlines
Tue 6/166:20 am
ORD
-
SJC
1 stop7h 04m
Alaska Airlines
Deal found 5/18$306
This Alaska Airlines deal was found by Cheapflights users on 5/17. 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 7/112:03 pm
SJC
-
ORD
1 stop14h 57m
Alaska Airlines
Wed 7/87:59 pm
ORD
-
SJC
1 stop15h 27m
Alaska Airlines
Deal found 5/17$307

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 May 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$282
(Delta)

One-way from

$144
(Delta)

Popular in

March

Cheapest in

February

Average price

$486

Good round-trip deal

$471 or less

Good one-way deal

$203 or less
Provider with most accurate pricing for San Jose-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for San Jose-Chicago (CHI) flights.
From San Jose to Chicago (CHI)
One-way flight from San Jose to Chicago (CHI)
Highest demand for flights based on searches. 1% potential increase in price ($8 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Average for round-trip flights in May 2026
Price to beat on a round-trip flight from San Jose to Chicago (CHI).
Price to beat on a one-way flight from San Jose to Chicago (CHI).

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 May 22, 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 6/23

9:54 am-9:57 pm

2 stops10h 03m

Chicago O'Hare Intl

Wed 6/24

8:36 am-5:17 pm

2 stops10h 41m

$288
Quickest round-trip

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Mon 6/22

10:55 pm-5:00 am

Nonstop4h 05m

Chicago Midway

Wed 7/1

8:55 pm-11:25 pm

Nonstop4h 30m

$332

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 6/10

7:35 pm-4:40 am

1 stop7h 05m

Chicago Midway

Tue 6/16

5:25 am-11:25 am

2 stops8h 00m

$355

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 6/16

8:55 pm-5:25 am

1 stop6h 30m

Chicago Midway

Tue 6/23

5:50 pm-11:00 pm

2 stops7h 10m

$355

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 6/16

9:54 am-9:57 pm

2 stops10h 03m

Chicago O'Hare Intl

Sat 6/20

7:45 am-12:38 pm

1 stop6h 53m

$357

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 6/11

7:13 am-11:36 pm

1 stop14h 23m

Chicago O'Hare Intl

Wed 7/1

6:20 am-11:24 am

1 stop7h 04m

$415

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 7/17

2:59 pm-11:18 pm

1 stop6h 19m

Chicago O'Hare Intl

Sun 7/19

6:30 am-3:46 pm

2 stops11h 16m

$432

San JoseChicago

SJC - RFD

SJCRFD

San Jose

Thu 9/24

9:10 am-8:39 pm

1 stop9h 29m

Chicago Greater Rockford

Sun 9/27

9:29 pm-1:29 pm

1 stop18h 00m

$436

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Fri 7/17

8:19 pm-8:37 am

2 stops10h 18m

Chicago Midway

Mon 7/20

9:19 am-5:12 pm

2 stops9h 53m

$437

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sat 6/6

11:41 am-12:08 am

2 stops10h 27m

Chicago O'Hare Intl

Tue 6/9

6:30 am-3:53 pm

2 stops11h 23m

$437

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/20

Showing 1-10 of 52 resultsSorted by cheapest first
1
2
3
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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 May.
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

What is the cheapest month to book a flight from San Jose, California to Chicago?

Currently, March is the cheapest month in which you can book a flight from San Jose, California to Chicago (average of $95). Flying from San Jose, California to Chicago in April is currently the most expensive (average of $265). 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 May 22, 2026.

A simple way to save on the total cost of your ticket is to fly from San Jose, California to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 18% 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 May 22, 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?

How far ahead should I book a flight from San Jose, California to Chicago?

The best time to book flights from San Jose, California to Chicago is 88 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.

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.

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.

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 May 22, 2026.
Peruse reviews from past customers who have flown with Alaska Airlines,Southwest, 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.

Crew

8.5

Food

7.0

Entertainment

7.0

Overall

7.9

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.

Crew

8.5

Food

7.0

Entertainment

7.0

Overall

7.9

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.

Crew

8.5

Food

7.0

Entertainment

7.0

Overall

7.9

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.

Crew

8.5

Food

7.0

Entertainment

7.0

Overall

7.9

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.

Crew

8.5

Food

7.0

Entertainment

7.0

Overall

7.9

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.

Crew

8.5

Food

7.0

Entertainment

7.0

Overall

7.9

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.

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 $332, Delta 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?

    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 American 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 $111, respectively.

  • What are the most popular routes 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 $645, our data indicates the cheapest price to be $226. The most popular route (San Jose - Chicago O'Hare Intl), is priced around $277.

  • 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, March is the cheapest month in which you can book a flight from San Jose, California to Chicago (average of $95). Flying from San Jose, California to Chicago in April is currently the most expensive (average of $265). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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.

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 May 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$121Average$239FlexibilityNo cancel feeOn-time65%
FrontierCheapest$131Average$294FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$200Average$424FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$235Average$339FlexibilityNo cancel feeOn-time75%
DeltaCheapest$236Average$378FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$270Average$517FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$278Average$554FlexibilityNo cancel feeOn-time69%

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