What’s the fastest layover option from Chicago to San Jose, California?

Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 10h 23m.

What’s the top layover airport for flights from Chicago to San Jose, California?

Denver (DEN) – chosen by Cheapflights users on 67% of 1-stop itineraries from Chicago to San Jose, California on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to San Jose, California?

Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of $170.

Which airport typically offers the quickest layover for flights from Chicago to San Jose, California?

Flights via Denver (DEN) offer the fastest connection on this route, with an average layover time of 2h 58m.

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

A quick flight from Chicago to San Jose, California can take about 7h 20m. Alaska Airlines provides one of the quickest options available for as low as $346. Chicago and San Jose, California are separated by a distance of 1832 mi. Both multi-stop and nonstop flights can be found to your destination and back.

What are the cheapest airlines flying from Chicago to San Jose, California round-trip?

Frontier, at $80, was found to be the cheapest airline from Chicago to San Jose, California.Alternate airlines to your destination round-trip include Spirit Airlines and Delta. Frontier is 80% cheaper than the average price of flights available within the next 90 days to this destination.

What are the cheapest airlines to fly from Chicago to San Jose, California one-way?

One-way options have recently been found by users for as low as $73 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $80 and Alaska Airlines from $89 one-way.

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

Booking 2 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to San Jose, California. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, October is the cheapest month in which you can book a flight from Chicago to San Jose, California (average of $80). Flying from Chicago to San Jose, California in November is currently the most expensive (average of $207). 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.

In terms of precipitation, rainfall in San Jose, California ranges from 0.0 - 3.1 inches per month. January is typically the wettest month, when rainfall can reach 3.1 in. July is typically the driest time to visit San Jose, California when rainfall is around 0.0 in.

If weather is an important factor for your trip to San Jose, California, 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 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 50.0 F).

What are the cheapest flights from Chicago to San Jose, California?

Looking for the cheapest flight from Chicago to San Jose, California? While on average our users pay $445, our data indicates the cheapest price to be $282. The most popular route (Chicago O'Hare Intl - San Jose), is priced around $231.

What are the most popular airlines that fly from Chicago to San Jose, California?

The most popular airlines flying from Chicago to San Jose, California are United Airlines, Southwest and Delta. Something to consider prior to booking your flight.

What is the cheapest time of day to fly from CHI to SJC?

One of the essential ways to save on airfare from Chicago to San Jose, California is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 34% on airfare.

Most accurate provider : When it comes to deals on Chicago-San Jose, California flights, users find the pricing of Gotogate to be most consistent on Cheapflights vs. Gotogate Users can find the same prices on Chicago-San Jose, California flight deals on Cheapflights vs. Gotogate >95% of the time. Price accuracy is based on data collected from Chicago-San Jose, California flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Chicago-San Jose, California flights, Cheapflights users trust Gotogate the most. Gotogate 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 Chicago-San Jose, California flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

What airport do you fly into for flights to San Jose from Chicago?

Located just 2.9 mi from the city center, San Jose is the airport most travelers will use when flying to San Jose from Chicago. Booking flights from Chicago to San Jose (SJC) should be relatively easy as there are 0 daily inbound flights from Chicago from 7 different airlines.

Can I find deals for flights from Chicago to San Jose that include hotel bookings?

Yes. In addition to deals on Chicago to San Jose flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Chicago to San Jose?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to San Jose.

Can I find deals for business class flights from Chicago to San Jose?

Yes. Cheapflights offers flight deals from Chicago to San Jose by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$71+ Flights from Chicago to San Jose, CA

Most accurate provider	Gotogate 3 stars
Most trusted provider	Gotogate 3 stars
Round-trip from	$184 (Alaska Airlines)
One-way from	$71 (Trip.com)
Popular in	December
Cheapest in	February
Average price	$399
Good round-trip deal	$430 or less
Good one-way deal	$323 or less

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*1 star
eDreams	Price Accuracy3 stars	Trust Score*3 stars
Gotogate	Price Accuracy3 stars	Trust Score*3 stars
JustAirTicket	Price Accuracy-	Trust Score*1 star

ORD

At ORD, Garrett Popcorn near gate B8 is a must-try snack before your flight.

MDW

For a quick check-in at MDW, use the indoor bridge to reach gates after security, reducing congestion and queues.

SJC

For a quick exit from SJC, use rideshare services with designated pick-up spots at all terminals.

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$80	Average$222	FlexibilityNo cancel fee	On-time62%
Spirit Airlines	Cheapest$133	Average$201	FlexibilityNo cancel fee	On-time65%
Delta	Cheapest$189	Average$384	FlexibilityNo cancel fee	On-timeN/A
Alaska Airlines	Cheapest$262	Average$361	FlexibilityNo cancel fee	On-time75%
Southwest	Cheapest$333	Average$484	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$336	Average$491	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$352	Average$620	FlexibilityNo cancel fee	On-time71%

$71+ Cheap flights from Chicago (CHI) to San Jose, CA (SJC)

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 2/1. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to San Jose with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Chicago to San Jose

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Chicago to San Jose

Cheapest flights from Chicago to San JoseExplore the most affordable flight options available from Chicago to San Jose. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 6, 2026.

Explore the most affordable flight options available from Chicago to San Jose. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 6, 2026.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to San Jose that are best for you.

Compare providers for flights from Chicago to San Jose

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 Chicago to San Jose in January.

Best time to book a flight from Chicago to San Jose

Have a flexible travel schedule? Discover the best time to fly to San Jose from Chicago with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Chicago to San Jose

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to San Jose. Price data was last updated on January 2, 2026.

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

What is the cheapest time of day to fly from CHI to SJC?

Find hourly flight availability from Chicago to San Jose. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 6, 2026.

What’s the top layover airport for flights from Chicago to San Jose, California?

Share of 1-stop round-trip flights from Chicago to San Jose, California chosen by Cheapflights users in the past 12 months, using the same layover each way.

What’s the cheapest layover airport for flights from Chicago to San Jose, California?

Average round-trip fare for 1-stop flights from Chicago to San Jose, California, chosen by Cheapflights users in the past 12 months, with the same layover each way.

What’s the fastest layover option from Chicago to San Jose, California?

Shortest average travel time for 1-stop one-way flights from Chicago to San Jose, California, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Which airport typically offers the quickest layover for flights from Chicago to San Jose, California?

Average layover duration for 1-stop one-way flights from Chicago to San Jose, California, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

The best insider tips for Chicago to San Jose 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 Chicago to San Jose trip

Airports

ORD

MDW

SJC

Our travel experts

Reviews of airlines servicing San Jose

Get a feel of what it's like to fly with Alaska Airlines, Southwest, and United Airlines from Chicago to San Jose by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Chicago to San Jose. 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 into for flights to San Jose from Chicago?

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

What are the cheapest airlines flying from Chicago to San Jose, California round-trip?

What are the cheapest airlines to fly from Chicago to San Jose, California one-way?

What are the cheapest flights from Chicago to San Jose, California?

Can I find deals for flights from Chicago to San Jose that include hotel bookings?

How can I find direct flights from Chicago to San Jose?

Can I find deals for business class flights from Chicago to San Jose?

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

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 Chicago to San Jose

See prices for flight routes from nearby airports that may be better suited for you.

Top 7 airlines flying from Chicago to San Jose

100% Free

Book with Flexibility

Travel Smart

Cheapest flights from Chicago to San Jose
Explore the most affordable flight options available from Chicago to San Jose. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 6, 2026.