Cheap flights from Chicago to San Jose from $60
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 7/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Chicago to San Jose
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Alaska Airlines flights from Chicago to San Jose
Our best Alaska Airlines deals on Chicago to San Jose flight tickets
Spirit Airlines flights from Chicago to San Jose
Our best Spirit Airlines deals on Chicago to San Jose flight tickets
See travel insights to San Jose from
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 typical price of a round-trip flight between Chicago and San Jose?
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 $293. 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 $458. 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 $600.
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 morning when prices are around $512.
What is the cheapest Chicago to San Jose flight route?
Fly from Chicago Midway 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 20 weeks ahead of your departure date. In general, you can expect to find flights to San Jose for around $402 when searching 20 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 27% 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 June 2025, prices for Chicago to San Jose flights are approximately 9% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Chicago to San Jose?
Spirit Airlines, Frontier, 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 50% 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 4 per day as of June 2025. The most frequent departure time is 2:00PM, with 59% of daily flights leaving in the afternoon.
How many flights depart from Chicago to San Jose on average per week?
31 flights are operational weekly from Chicago to San Jose as of June 2025. The most popular departure day for this route is Mon, with 26% 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 June 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 (24.82% of total bookings). The next most popular plane models are Airbus A320-100/200 (13.69%), Airbus A319 (12.77%), and Boeing 737-900 Passenger/BBJ3 (winglets) (7.85%).
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 United Airlines (34% of total bookings). The next most popular airlines are Southwest (31%), Spirit Airlines (18%), and Frontier (12%).
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 3,295 reviews | |||
| PriceFrom $127 | Free Cancellation | Rating 6.3 8,052 reviews | |||
| PriceFrom $277 | Free Cancellation | Rating 8.0 7,946 reviews | |||
| PriceFrom $307 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom $370 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $376 | Free Cancellation | Rating 8.0 4,287 reviews |
Southwest Flights From Chicago to San Jose
Southwest flight deals from Chicago to San Jose start from $376 round-trip. Over the 27 Southwest flights for this route in a normal week, average airfare is usually $478 round-trip - but some users have found much cheaper deals with momondo.
United Airlines Flights From Chicago to San Jose
Across 8,790 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Chicago to San Jose about 4 times each week, with ticket deals ranging from $307 to $496. 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.