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$116+ 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 6/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheapflights Tip: The best prices from San Jose to Chicago are usually found in January or September, booked 80 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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$226
(Mytrip)

One-way from

$116
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$434

Good round-trip deal

$393 or less

Good one-way deal

$195 or less
Provider with most accurate pricing for San Jose-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for San Jose-Chicago (CHI) flights.
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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, 6% potential price rise
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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 May 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 May 1, 2025.

This Mytrip deal was found by Cheapflights users on 4/29. 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.
Fri 5/306:00 amSJC - ORD
3 stops27h 50mSpirit Airlines
Tue 6/39:02 pmORD - SJC
1 stop28h 27mSpirit Airlines
Deal found 4/29$226
This Booking.com deal was found by Cheapflights users on 4/29. 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.
Mon 5/512:20 pmSJC - ORD
1 stop9h 21mFrontier
Thu 5/88:14 pmORD - SJC
1 stop24h 27mFrontier
Deal found 4/29$228
This CheapOair deal was found by Cheapflights users on 4/29. 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.
Mon 5/127:41 pmSJC - ORD
1 stop7h 29mMultiple Airlines
Thu 5/159:02 pmORD - SJC
1 stop15h 03mMultiple Airlines
Deal found 4/29$234
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/112:13 pmSJC - MDW
1 stop6h 40mFrontier
Mon 6/96:25 amMDW - SJC
1 stop9h 15mFrontier
Deal found 4/30$238
This Delta deal was found by Cheapflights users on 4/29. 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 5/2010:25 pmSJC - MDW
1 stop9h 15mDelta
Wed 5/211:55 pmMDW - SJC
1 stop8h 36mDelta
Deal found 4/29$299
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/46:30 amSJC - ORD
1 stop5h 58mDelta
Wed 6/47:15 pmORD - SJC
1 stop6h 26mDelta
Deal found 4/30$299
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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 6/177:03 amSJC - ORD
1 stop13h 27mAlaska Airlines
Tue 6/2410:00 amORD - SJC
1 stop11h 15mAlaska Airlines
Deal found 4/29$304
This Trip.com deal was found by Cheapflights users on 4/29. 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.
Fri 5/306:00 amSJC - MDW
2 stops36h 53mMultiple Airlines
Mon 6/26:25 amMDW - SJC
1 stop9h 15mMultiple Airlines
Deal found 4/29$313
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/211:11 pmSJC - ORD
1 stop9h 04mUnited Airlines
Sat 5/247:59 pmORD - SJC
Nonstop4h 40mUnited Airlines
Deal found 4/30$321
This Southwest deal was found by Cheapflights users on 4/29. 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 6/64:25 pmSJC - MDW
1 stop5h 45mSouthwest
Wed 6/117:30 pmMDW - SJC
Nonstop4h 35mSouthwest
Deal found 4/29$371
This Mytrip deal was found by Cheapflights users on 4/28. 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 7/36:00 amSJC - RFD
2 stops28h 10mMultiple Airlines
Sat 7/511:03 amRFD - SJC
3 stops27h 23mMultiple Airlines
Deal found 4/28$673

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 1, 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

Fri 5/30

6:00 am-11:50 am

3 stops27h 50m

Chicago O'Hare Intl

Tue 6/3

9:02 pm-11:29 pm

1 stop28h 27m

$226

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 5/12

7:41 pm-5:10 am

1 stop7h 29m

Chicago O'Hare Intl

Thu 5/15

9:02 pm-10:05 am

1 stop15h 03m

$234

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sun 6/1

12:13 pm-8:53 pm

1 stop6h 40m

Chicago Midway

Mon 6/9

6:25 am-1:40 pm

1 stop9h 15m

$238

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 5/29

2:33 pm-8:53 pm

1 stop28h 20m

Chicago O'Hare Intl

Thu 6/5

6:00 am-11:18 am

1 stop7h 18m

$241

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 5/20

10:25 pm-9:40 am

1 stop9h 15m

Chicago Midway

Wed 5/21

1:55 pm-8:31 pm

1 stop8h 36m

$299

San JoseChicago

SJC - ORD

SJCORD

San Jose

Wed 6/4

6:30 am-2:28 pm

1 stop5h 58m

Chicago O'Hare Intl

Wed 6/4

7:15 pm-11:41 pm

1 stop6h 26m

$299

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 5/27

6:45 am-11:56 pm

2 stops15h 11m

Chicago O'Hare Intl

Tue 6/3

8:00 am-8:14 pm

1 stop14h 14m

$300

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sat 5/24

6:35 am-12:57 pm

Nonstop4h 22m

Chicago O'Hare Intl

Wed 6/4

7:59 pm-10:39 pm

Nonstop4h 40m

$311

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Fri 5/30

6:00 am-8:53 pm

2 stops36h 53m

Chicago Midway

Mon 6/2

6:25 am-1:40 pm

1 stop9h 15m

$313

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Fri 6/6

4:25 pm-12:10 am

1 stop5h 45m

Chicago Midway

Wed 6/11

7:30 pm-10:05 pm

Nonstop4h 35m

$371

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
GotogatePrice Accuracy3 starsTrust Score*2 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 eDreams the most. eDreams 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.

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 April 25, 2025.

The best time to book flights from San Jose to Chicago is 80 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 May 1, 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 24% 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 March 30, 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.

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 May 1, 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
9,972 reviews

Entertainment

7.1

Overall

8.0

Boarding

8.1

Crew

8.5

Comfort

7.9

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
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Entertainment

7.1

Overall

8.0

Boarding

8.1

Crew

8.5

Comfort

7.9

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
4,294 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Entertainment

7.1

Overall

8.0

Boarding

8.1

Crew

8.5

Comfort

7.9

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
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Entertainment

7.1

Overall

8.0

Boarding

8.1

Crew

8.5

Comfort

7.9

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
7.9
Good
2,406 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Entertainment

7.1

Overall

8.0

Boarding

8.1

Crew

8.5

Comfort

7.9

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
8,696 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Entertainment

7.1

Overall

8.0

Boarding

8.1

Crew

8.5

Comfort

7.9

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 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 $226. Other airlines that can offer you cheap pricing are Frontier, from $228, and Delta, from $299. You may be able to fly from San Jose to Chicago for 43% 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 $116 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $116 and Alaska Airlines from $147 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 $963, our data indicates the cheapest price to be $171. The most popular route (San Jose - Chicago O'Hare Intl), is priced around $114.

  • 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$98Average$245FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$134Average$265FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$197Average$297FlexibilityNo cancel feeOn-time75%
DeltaCheapest$236Average$501FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$279Average$549FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$287Average$491FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$367Average$503FlexibilityNo cancel feeOn-time63%

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