HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$82+ 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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — CHI
Dec 25 — Jan 11
Wed 12/25
Wed 1/1
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from San Jose to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

The best prices from San Jose to Chicago are usually found in September or November, booked 61 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

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 December 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$178
(FlightHub)

One-way from

$82
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$496
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
High demand for flights, 4% potential price rise
Search Deals
Best time to find cheap flights, 2% potential price drop
Search Deals
Average for round-trip flights in December 2024
Search Deals

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 December 20, 2024.

This Justfly.com deal was found by Cheapflights users on 12/19. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/278:10 pmSJC - ORD
1 stop7h 20mSpirit Airlines
Sun 1/59:54 pmORD - SJC
1 stop11h 52mSpirit Airlines
Deal found 12/19$310
This FlightHub deal was found by Cheapflights users on 12/19. 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.
Mon 12/2312:30 pmSJC - ORD
1 stop9h 16mMultiple Airlines
Mon 1/69:54 pmORD - SJC
1 stop13h 41mMultiple Airlines
Deal found 12/19$323
This Frontier deal was found by Cheapflights users on 12/19. 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.
Wed 12/2512:30 pmSJC - ORD
1 stop9h 16mFrontier
Fri 1/36:00 amORD - SJC
1 stop7h 45mFrontier
Deal found 12/19$404
This FlightHub deal was found by Cheapflights users on 12/20. 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 12/2612:40 pmSJC - MDW
1 stop28h 52mFrontier
Mon 12/3010:04 pmMDW - SJC
1 stop14h 16mFrontier
Deal found 12/20$543
This Alaska Airlines deal was found by Cheapflights users on 12/19. 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 12/316:15 amSJC - ORD
2 stops15h 44mAlaska Airlines
Sat 1/47:00 amORD - SJC
1 stop7h 54mAlaska Airlines
Deal found 12/19$658
This Southwest deal was found by Cheapflights users on 12/19. 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.
Fri 12/279:45 amSJC - MDW
Nonstop4h 05mSouthwest
Sun 1/56:10 amMDW - SJC
1 stop7h 20mSouthwest
Deal found 12/19$722
This United deal was found by Cheapflights users on 12/19. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2710:40 pmSJC - ORD
Nonstop4h 17mUnited Airlines
Thu 1/28:00 pmORD - SJC
Nonstop4h 49mUnited Airlines
Deal found 12/19$738
This Delta deal was found by Cheapflights users on 12/19. 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 12/276:15 amSJC - MDW
1 stop9h 29mDelta
Sun 1/55:04 pmMDW - SJC
2 stops8h 55mDelta
Deal found 12/19$762
This eDestinos deal was found by Cheapflights users on 12/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/205:30 pmSJC - MDW
1 stop28h 57mMultiple Airlines
Sun 12/298:41 pmMDW - SJC
1 stop28h 40mMultiple Airlines
Deal found 12/19$822
This Delta deal was found by Cheapflights users on 12/19. 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 12/276:25 amSJC - ORD
2 stops12h 34mDelta
Sun 1/53:18 pmORD - SJC
2 stops10h 41mDelta
Deal found 12/19$835
This Southwest deal was found by Cheapflights users on 12/19. 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 12/267:00 amSJC - ORD
2 stops9h 10mSouthwest
Wed 1/14:00 pmORD - SJC
1 stop7h 30mSouthwest
Deal found 12/19$857
This Mytrip deal was found by Cheapflights users on 12/19. 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.
Sat 12/218:10 pmSJC - RFD
1 stop13h 40mMultiple Airlines
Sat 12/2811:47 amRFD - SJC
2 stops21h 59mMultiple Airlines
Deal found 12/19$946

Find flights from San Jose to Chicago within your budget

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 December 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 1/16

5:19 pm-7:28 pm

1 stop24h 09m

Chicago O'Hare Intl

Sun 1/19

7:25 am-12:11 pm

1 stop6h 46m

$178

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 2/21

9:18 pm-6:07 am

1 stop6h 49m

Chicago O'Hare Intl

Sun 2/23

10:39 pm-10:21 am

1 stop13h 42m

$179

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 2/26

4:03 pm-12:17 am

1 stop6h 14m

Chicago Midway

Wed 3/5

7:05 am-5:06 pm

2 stops36h 01m

$212

San JoseChicago

SJC - ORD

SJCORD

San Jose

Wed 4/16

4:03 pm-12:42 am

1 stop6h 39m

Chicago O'Hare Intl

Tue 4/22

1:00 pm-7:04 pm

1 stop8h 04m

$282

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 1/9

11:12 am-1:07 pm

1 stop23h 55m

Chicago O'Hare Intl

Mon 1/13

3:35 pm-11:27 pm

2 stops9h 52m

$302

San JoseChicago

SJC - ORD

SJCORD

San Jose

Wed 2/26

2:25 pm-11:56 pm

1 stop7h 31m

Chicago O'Hare Intl

Wed 3/5

5:45 am-3:01 pm

2 stops11h 16m

$310

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 2/26

6:40 am-4:20 pm

1 stop7h 40m

Chicago Midway

Wed 3/5

6:00 am-12:08 pm

1 stop8h 08m

$318

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 4/16

6:40 am-12:50 pm

Nonstop4h 10m

Chicago Midway

Tue 4/22

8:40 am-11:15 am

Nonstop4h 35m

$433

San JoseChicago

SJC - ORD

SJCORD

San Jose

Wed 2/26

6:20 am-12:35 pm

Nonstop4h 15m

Chicago O'Hare Intl

Tue 3/4

9:08 am-12:03 pm

Nonstop4h 55m

$433

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 4/17

9:10 am-10:20 pm

2 stops11h 10m

Chicago O'Hare Intl

Mon 4/21

7:00 am-2:40 pm

1 stop9h 40m

$457

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/19

Showing 1-10 of 24 results
1
2
3

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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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-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-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Jose-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San Jose-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-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.

Travel insights for flights from San Jose to Chicago

Get recent, data-driven insights about flights from San Jose to Chicago including ideal travel times, pricing trends, and more.

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 December 13, 2024.

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 $317). 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 December 20, 2024.

A simple way to save on the total cost of your ticket is to fly from San Jose to Chicago in the evening. 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 morning.

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 December 16, 2024.

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

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 December 20, 2024.
Get a feel of what it's like to fly with Frontier, Spirit Airlines and Alaska Airlines 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.
Southwest
8.1
Very good
4,821 reviews

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Southwest
8.1
Very good
4,821 reviews
Southwest
8.1
Very good
4,821 reviews

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Alaska Airlines
8.0
Very good
9,547 reviews
Southwest
8.1
Very good
4,821 reviews

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Delta
8.0
Very good
8,601 reviews
Southwest
8.1
Very good
4,821 reviews

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

United Airlines
7.4
Good
9,041 reviews
Southwest
8.1
Very good
4,821 reviews

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,821 reviews

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

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 is 1 daily outbound flight 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 $178. Other airlines that can offer you cheap pricing are Spirit Airlines, from $179, and Alaska Airlines, from $302. You may be able to fly from San Jose to Chicago for 57% 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 $82 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $82 and Delta from $146 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 $543, our data indicates the cheapest price to be $149. The most popular route (San Jose - Chicago O'Hare Intl), is priced around $139.

  • 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 $317). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for San Jose to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Los Angeles to Midway flights
Ontario to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
San Diego to O'Hare Intl flights
Burbank to O'Hare Intl flights
San Francisco to Midway flights
San Jose to O'Hare Intl flights
Las Vegas to O'Hare Intl flights
Oakland to O'Hare Intl flights
Sacramento to O'Hare Intl flights
Ontario to Midway flights
Las Vegas to Midway flights
San Diego to Midway flights
Los Angeles to St. Louis flights
San Francisco to St. Louis flights
Santa Ana to Midway flights
Palm Springs to O'Hare Intl flights
Burbank to Midway flights
Fresno to O'Hare Intl flights
Ontario to St. Louis flights
Reno to O'Hare Intl flights
San Jose to Midway flights
Oakland to Midway flights
Las Vegas to St. Louis flights
Sacramento to Midway flights
Long Beach to O'Hare Intl flights
Santa Barbara to O'Hare Intl flights
San Diego to St. Louis flights
Burbank to St. Louis flights
Sacramento to St. Louis flights
Medford to O'Hare Intl flights
San Jose to St. Louis flights
Medford to Midway flights
Las Vegas to Rockford flights
Santa Ana to St. Louis flights
Palm Springs to Midway flights
Fresno to Midway flights
Santa Ana to Peoria flights
Long Beach to St. Louis flights
Bakersfield to O'Hare Intl flights
Long Beach to Midway flights
San Diego to Moline flights
Fresno to St. Louis flights
Burbank to Moline flights
Reno to Midway flights
Los Angeles to Rockford flights
Los Angeles to Peoria flights
San Luis Obispo to O'Hare Intl flights

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 December 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$100Average$276FlexibilityNo cancel feeOn-time75%
FrontierCheapest$106Average$241FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$134Average$266FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$203Average$516FlexibilityNo cancel feeOn-time69%
DeltaCheapest$236Average$501FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$279Average$535FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$367Average$549FlexibilityNo cancel feeOn-time63%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.