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

According to our current data, Alaska Airlines ($289), Spirit Airlines ($290), and Delta ($292) offers the cheapest pricing from Chicago to San Jose. Alaska Airlines is priced at 29% 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 Spirit Airlines ($113), Frontier ($132), and Hawaiian Airlines ($135).

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 58 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 $344). 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. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 $403, our data indicates the cheapest price to be $117. The most popular route (Chicago O'Hare Intl - San Jose), is priced around $172.

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, Delta and Frontier. Something to consider prior to booking your flight.

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

Users have found that flying from Chicago to San Jose on a Sunday typically leans towards higher prices. However, this doesn’t mean you still can’t find a deal. Flexibility with other aspects of your flight can still land a great price for your trip.

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

To save on the cost of your flight from Chicago to San Jose, book at least 59 days before your planned departure. Booking around this time can save you about 110% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $297 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $424.

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

October can be a great time to fly to San Jose from Chicago with a flight ticket averaging about $411. Cheapflights users have found deals in the month of October for as cheap as $143. The most expensive prices can be found in the month of June.

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 morning tend to be the most expensive. A flight at noon could potentially save you up to 14% 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 4 daily inbound flights from Chicago from 6 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.

$113+ Flights from Chicago to San Jose

Round-trip from	$289 (Alaska Airlines)
One-way from	$113 (Mytrip)
Popular in	June
Cheapest in	October
Average price	$476
Good round-trip deal	$407 or less
Good one-way deal	$252 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$248	FlexibilityNo cancel fee	On-time62%
Spirit Airlines	Cheapest$127	Average$243	FlexibilityNo cancel fee	On-time65%
Delta	Cheapest$277	Average$387	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$307	Average$496	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$370	Average$472	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$376	Average$478	FlexibilityNo cancel fee	On-time63%

$113+ 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 11/5. 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 August, booked 58 days in advance, depart on a Wednesday or Thursday and return on a Tuesday

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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 June 12, 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 June 12, 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

Airports

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 June 9, 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 June 12, 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 June 8, 2025.

Rainfall in San Jose by month

Plan your trip to San Jose by taking into account the average rainfall totals by month.

Temperature in San Jose by month

Plan your trip to San Jose by taking into account the average temperature totals by month.

Reviews of airlines servicing San Jose

See what other customers who have flown with Alaska Airlines, Southwest and Delta from Chicago to San Jose have to say. In addition to providing an overall rating, 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?

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 6 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 June 12, 2025.