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$73+ 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — CHI
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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The best prices from San Jose to Chicago are usually found in September or January, booked 59 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 November 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

March

Cheapest in

September

Round-trip from

$168
(Frontier)

One-way from

$73
(Trip.com)
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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High demand for flights, 21% potential price rise
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Best time to find cheap flights, 14% potential price drop
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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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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 November 20, 2024.

This Frontier deal was found by Cheapflights users on 11/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/132:28 pmSJC - MDW
1 stop7h 45mFrontier
Mon 12/167:15 amMDW - SJC
1 stop6h 53mFrontier
Deal found 11/20$168
This Frontier deal was found by Cheapflights users on 11/19. 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.
Fri 12/62:28 pmSJC - ORD
1 stop8h 07mFrontier
Sun 12/87:25 amORD - SJC
1 stop6h 43mFrontier
Deal found 11/19$168
This Mytrip deal was found by Cheapflights users on 11/19. 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.
Thu 12/59:20 pmSJC - ORD
2 stops15h 06mSpirit Airlines
Tue 12/109:10 pmORD - SJC
2 stops17h 37mSpirit Airlines
Deal found 11/19$169
This Mytrip deal was found by Cheapflights users on 11/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2811:30 amSJC - ORD
1 stop9h 14mMultiple Airlines
Tue 1/79:54 pmORD - SJC
1 stop13h 41mMultiple Airlines
Deal found 11/18$176
This eDestinos deal was found by Cheapflights users on 11/18. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/296:06 pmSJC - MDW
2 stops33h 27mMultiple Airlines
Tue 1/78:15 amMDW - SJC
2 stops17h 31mMultiple Airlines
Deal found 11/18$212
This Alaska Airlines deal was found by Cheapflights users on 11/19. 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 12/1012:47 pmSJC - ORD
1 stop9h 00mAlaska Airlines
Wed 12/111:07 pmORD - SJC
1 stop8h 23mAlaska Airlines
Deal found 11/19$326
This Delta deal was found by Cheapflights users on 11/19. 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.
Tue 12/1010:10 amSJC - ORD
2 stops8h 18mDelta
Thu 12/126:05 amORD - SJC
1 stop10h 00mDelta
Deal found 11/19$345
This Delta deal was found by Cheapflights users on 11/19. 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.
Tue 12/1012:35 pmSJC - MDW
1 stop7h 31mDelta
Fri 12/132:15 pmMDW - SJC
1 stop8h 52mDelta
Deal found 11/19$346
This United Airlines deal was found by Cheapflights users on 11/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/146:30 amSJC - ORD
Nonstop4h 20mUnited Airlines
Wed 12/189:05 amORD - SJC
Nonstop4h 49mUnited Airlines
Deal found 11/20$383
This Southwest deal was found by Cheapflights users on 11/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/304:45 pmSJC - MDW
1 stop6h 30mSouthwest
Tue 1/78:35 amMDW - SJC
Nonstop4h 50mSouthwest
Deal found 11/18$418
This Mytrip deal was found by Cheapflights users on 11/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/195:50 amSJC - RFD
3 stops24h 35mMultiple Airlines
Sun 12/2212:40 pmRFD - SJC
1 stop12h 41mMultiple Airlines
Deal found 11/18$522
This Mytrip deal was found by Cheapflights users on 11/19. 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.
Wed 11/205:26 pmSJC - MDW
1 stop14h 02mVolaris
Thu 11/2110:41 pmMDW - SJC
1 stop17h 28mVolaris
Deal found 11/19$776

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Fri 12/13

2:28 pm-12:13 am

1 stop7h 45m

Chicago Midway

Sun 12/15

7:15 am-12:08 pm

1 stop6h 53m

$168

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 12/6

2:28 pm-12:35 am

1 stop8h 07m

Chicago O'Hare Intl

Sun 12/8

7:25 am-12:08 pm

1 stop6h 43m

$168

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 12/5

9:20 pm-2:26 pm

2 stops15h 06m

Chicago O'Hare Intl

Tue 12/10

9:10 pm-12:47 pm

2 stops17h 37m

$169

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sat 12/28

11:30 am-10:44 pm

1 stop9h 14m

Chicago O'Hare Intl

Tue 1/7

9:54 pm-9:35 am

1 stop13h 41m

$176

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sun 12/29

6:06 pm-5:33 am

2 stops33h 27m

Chicago Midway

Tue 1/7

8:15 am-11:46 pm

2 stops17h 31m

$212

San JoseChicago

SJC - RFD

SJCRFD

San Jose

Thu 2/20

10:51 am-8:52 pm

1 stop8h 01m

Chicago Greater Rockford

Sun 2/23

9:42 pm-9:51 am

1 stop14h 09m

$310

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 12/10

12:47 pm-11:47 pm

1 stop9h 00m

Chicago O'Hare Intl

Wed 12/11

1:07 pm-7:30 pm

1 stop8h 23m

$326

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 12/10

10:10 am-8:28 pm

2 stops8h 18m

Chicago O'Hare Intl

Thu 12/12

6:05 am-2:05 pm

1 stop10h 00m

$345

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 12/10

12:35 pm-10:06 pm

1 stop7h 31m

Chicago Midway

Fri 12/13

2:15 pm-9:07 pm

1 stop8h 52m

$346

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 1/16

7:40 am-4:35 pm

1 stop6h 55m

Chicago Midway

Mon 1/20

9:45 am-12:35 pm

Nonstop4h 50m

$408

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 23 results
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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 November.
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 November 15, 2024.

The best time to book flights from San Jose to Chicago is 59 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, September is the cheapest month in which you can book a flight from San Jose to Chicago (average of $232). Flying from San Jose to Chicago in June is currently the most expensive (average of $308). 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 November 20, 2024.

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 30% 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 November 18, 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. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from San Jose 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 November 20, 2024.

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).

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 November 20, 2024.
Get a feel of what it's like to fly with Spirit Airlines, Alaska Airlines and Frontier 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
5,014 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Overall

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
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Overall

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
9,461 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Overall

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
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Overall

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
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Overall

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

Volaris
6.7
Okay
1,287 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Overall

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 are 2 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 $168. Other airlines that can offer you cheap pricing are Spirit Airlines, from $169, and Alaska Airlines, from $326. You may be able to fly from San Jose to Chicago for 58% 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 $73 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $74 and Delta from $158 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 $863, our data indicates the cheapest price to be $149. The most popular route (San Jose - Chicago O'Hare Intl), is priced around $111.

  • 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, September is the cheapest month in which you can book a flight from San Jose to Chicago (average of $232). Flying from San Jose to Chicago in June is currently the most expensive (average of $308). 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.

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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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$100Average$297FlexibilityNo cancel feeOn-time75%
Spirit AirlinesCheapest$111Average$264FlexibilityNo cancel feeOn-time65%
FrontierCheapest$128Average$220FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$203Average$515FlexibilityNo cancel feeOn-time69%
DeltaCheapest$236Average$496FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$279Average$515FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$358Average$512FlexibilityNo cancel feeOn-time63%
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