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

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?

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

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

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?

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

How much does it cost to fly round-trip from Chicago to San Jose?

Airfare is below average for this route at the moment. Chicago to San Jose flights typically cost between $324 and $648 in October. The cheapest round-trip price found within the last 3 days was $188 on Frontier (Oct 31-Nov 3).

How long is the flight from Chicago to San Jose?

Departing from Chicago to San Jose will take you 4h 30m. The distance between Chicago and San Jose 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 Chicago to San Jose round-trip?

According to our current data, Frontier ($90), Spirit Airlines ($133), and Alaska Airlines ($188) offers the cheapest pricing from Chicago to San Jose. Frontier is priced at 78% lower than the current average price of a flight leaving 3 months from now.

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

The cheapest airlines for a one-way flight from Chicago to San Jose are Hawaiian Airlines ($109), Alaska Airlines ($115), and Delta ($130).

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

The price you pay for your flight from Chicago to San Jose may vary depending on when you book. For the best chance of a lower fare, look to book 19 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, September is the cheapest month in which you can book a flight from Chicago to San Jose (average of $255). Flying from Chicago to San Jose in June is currently the most expensive (average of $359). 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 day to fly from Chicago to San Jose?

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

Weekly flight availability from Chicago to San Jose

The most flights from CHI to SJC are scheduled on a Monday (5 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

In terms of precipitation, rainfall in San Jose 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 when rainfall is around 0.0 in.

If weather is an important factor for your trip to San Jose, 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?

Looking for the cheapest flight from Chicago to San Jose? While on average our users pay $398, our data indicates the cheapest price to be $131. The most popular route (Chicago O'Hare Intl - San Jose), is priced around $195.

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

The most popular airlines flying from Chicago to San Jose are American Airlines, Alaska Airlines 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 is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 16% on airfare.

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 3 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.

$79+ Cheap Flights from Chicago to San Jose

Round-trip from	$188 (Frontier)
One-way from	$79 (Kiwi.com)
Popular in	September
Cheapest in	October
Average price	$517
Good round-trip deal	$343 or less
Good one-way deal	$155 or less

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$90	Average$244	FlexibilityNo cancel fee	On-time62%
Spirit Airlines	Cheapest$133	Average$257	FlexibilityNo cancel fee	On-time65%
Alaska Airlines	Cheapest$188	Average$371	FlexibilityNo cancel fee	On-time75%
Delta	Cheapest$265	Average$382	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$314	Average$515	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$333	Average$483	FlexibilityNo cancel fee	On-time63%
American Airlines	Cheapest$352	Average$530	FlexibilityNo cancel fee	On-time71%

$79+ Cheap flights from Chicago (CHI) to San Jose (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 10/3. 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

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Cheapflights Tip: The best prices from Chicago to San Jose are usually found in October or February, booked 19 days in advance, depart on a Wednesday or Thursday and return on a Tuesday

Cheap flight deals from Chicago to San Jose

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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 September 17, 2025.

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 September 17, 2025.

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

The best insider tips for Chicago to San Jose flights

Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to San Jose trip

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ORD

MDW

SJC

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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?

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 September 12, 2025.

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

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 September 17, 2025.

What is the cheapest day to fly from Chicago to San Jose?

Use this chart to determine the cheapest time to fly round-trip from Chicago to San Jose. Price data was last updated on September 14, 2025.

Weekly flight availability from Chicago to San Jose

Explore weekly flight availability from Chicago to San Jose. 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 September 17, 2025.

How much does it cost to fly round-trip from Chicago to San Jose?

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

Share of 1-stop round-trip flights from Chicago to San Jose 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?

Average round-trip fare for 1-stop flights from Chicago to San Jose, 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?

Shortest average travel time for 1-stop one-way flights from Chicago to San Jose, 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?

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

Reviews of airlines servicing San Jose

Get a feel of what it's like to fly with Southwest, Delta, 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?

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

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

What are the cheapest flights from Chicago to San Jose?

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?

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Alternative routes for Chicago to San Jose

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Top 7 airlines flying from Chicago to San Jose

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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 September 17, 2025.