Cheap flights from Chicago to San Jose from $68
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to San Jose departing on 10/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Spirit Airlines flights from Chicago to San Jose
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Frontier flights from Chicago to San Jose
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How to get the cheapest flight ticket from Chicago to San Jose
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to San Jose?
In general, October is the cheapest month to fly from Chicago to San Jose. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $302. If you aren’t able to travel to San Jose during the month of October, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $371.
What is the cheapest day to depart on your flight to San Jose?
The cheapest day to depart on your flight to San Jose is on a Wednesday when prices can be found for as low as $446. This is often the case because there is less demand to fly during this day of the week. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to San Jose on Monday is $602.
What is the cheapest time of day to depart on your flight to San Jose?
Our most recent data shows that the best time of day to fly to San Jose is in the afternoon. Flights from Chicago to San Jose during this time can be as low as $443. In contrast, the most expensive time of day to depart to San Jose is in the evening when prices are around $521.
What is the cheapest Chicago to San Jose flight route?
Fly from Chicago O'Hare Intl to San Jose for the best Chicago - San Jose flight prices
How far in advance should I book a flight to San Jose?
You are more likely to see cheaper flights to San Jose from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San Jose for around $403 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San Jose from Chicago for as low as $276 on momondo.
What cabin class options are available on Chicago to San Jose flights?
There are 4 cabin classes available to choose from on Chicago to San Jose flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Chicago to San Jose flights?
You could potentially save up to 22% on your flight if you consider stops on a Chicago to San Jose flight.
How have Chicago to San Jose flight prices changed over time?
As of July 2025, prices for Chicago to San Jose flights are approximately 25% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Chicago to San Jose?
Frontier, Spirit Airlines, and Hawaiian Airlines are the most popular carriers operating from Chicago to San Jose
What airlines fly to San Jose?
United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to San Jose from Chicago according to our data. United Airlines is the first choice among our users, with 49% of people opting to fly with this airline when traveling to San Jose. Keep in mind that there are 8 different airlines that fly to San Jose on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to San Jose on average per day?
The number of flights available between Chicago and San Jose is 3 per day as of July 2025. The most frequent departure time is 10:00AM, with 50% of daily flights leaving in the afternoon.
How many flights depart from Chicago to San Jose on average per week?
27 flights are operational weekly from Chicago to San Jose as of July 2025. The most popular departure day for this route is Thu, with 30% of flights per week taking off on this day.
When to book flights from Chicago to San Jose
Cheap Chicago to San Jose (CHI to SJC) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to San Jose
How far is Chicago to San Jose by plane?
San Jose is 1836.7 mi away from Chicago. Flights usually cover this in 4h 30m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago to San Jose Airport?
Prices for flights from Chicago to San Jose Airport refresh daily.
How many operators does momondo search for flights from Chicago to San Jose Airport?
As of July 2025, there are 6 operators available to choose from for flights from Chicago to San Jose Airport.
How old do you have to be to fly from Chicago to San Jose Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to San Jose Airport.
What documentation or ID do you need to fly to San Jose Airport?
The travel and health documents required for your trip to San Jose Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at San Jose Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to San Jose?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to San Jose is Boeing 737 MAX 8 (29.03% of total bookings). The next most popular plane models are Airbus A320-100/200 (15.67%), Airbus A319 (10.60%), and Boeing 757-300 (6.68%).
What is the most popular airline from Chicago to San Jose?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago to San Jose is Southwest (34% of total bookings). The next most popular airlines are United Airlines (33%), Spirit Airlines (17%), and Frontier (11%).
Best airlines flying from Chicago to San Jose
Compare and see reviews for airlines that fly from Chicago to San Jose with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $90 | Free Cancellation | Rating 5.9 3,284 reviews | |||
| PriceFrom $127 | Free Cancellation | Rating 6.3 8,094 reviews | |||
| PriceFrom $277 | Free Cancellation | Rating 8.0 7,983 reviews | |||
| PriceFrom $317 | Free Cancellation | Rating 7.4 8,861 reviews | |||
| PriceFrom $370 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $376 | Free Cancellation | Rating 8.0 4,270 reviews |
Southwest Flights From Chicago to San Jose
Southwest flight deals from Chicago to San Jose start from $376 round-trip. Over the 18 Southwest flights for this route in a normal week, average airfare is usually $482 round-trip - but some users have found much cheaper deals with momondo.
United Airlines Flights From Chicago to San Jose
Across 8,861 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Chicago to San Jose about 9 times each week, with ticket deals ranging from $317 to $504. Price data is based on momondo searches in the last 72 hours.
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to San Jose?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to San Jose. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Chicago to San Jose with flexible booking policies on momondo?
momondo does allow users to show only those flights to San Jose from Chicago which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Chicago to San Jose?
momondo provides multiple filters to help you find the best flight to San Jose from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Chicago to San Jose right now. Can momondo alert me if prices change?
Price alerts on flights to San Jose from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.