Cheap flights from San Jose to Chicago from $53
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San Jose to Chicago departing on 4/2. 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 San Jose to Chicago
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Alaska Airlines flights from San Jose to Chicago
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How to get the cheapest flight ticket from San Jose to Chicago
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 San Jose and Chicago?
What is the cheapest month to fly to Chicago?
The month of January is, on average, the cheapest month to fly to Chicago from San Jose, with most prices found around $305. If you’re not able to fly to Chicago in January, then September is your next best option. Flight prices from San Jose to Chicago during September average around $355.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $481. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from San Jose to Chicago for around $595.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from San Jose to Chicago during this time can be as low as $526. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $568.
What is the cheapest San Jose to Chicago flight route?
Fly from San Jose to Chicago Midway for the best San Jose - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from San Jose when booking 25 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $459 when searching 25 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from San Jose for as low as $256 on momondo.
What cabin class options are available on San Jose to Chicago flights?
There are 4 cabin classes available to choose from on San Jose to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from San Jose to Chicago?
Spirit Airlines, Frontier, and Delta are the most popular carriers operating from San Jose to Chicago
What airlines fly to Chicago?
United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Chicago from San Jose according to our data. United Airlines is the first choice among our users, with 53% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from San Jose to Chicago on average per day?
As of March 2025, 1 flights take off from San Jose and land in Chicago each day. The most common flight departure time for this route is 6:00AM, with 100% of daily flights taking off at noon.
How many flights depart from San Jose to Chicago on average per week?
8 flights are operational weekly from San Jose to Chicago as of March 2025. The most popular departure day for this route is Sun, with 38% of flights per week taking off on this day.
When to book flights from San Jose to Chicago
Cheap San Jose to Chicago (SJC to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from San Jose to Chicago
How far is San Jose to Chicago by plane?
The straight-line distance from San Jose to Chicago is 1836.7 mi. By plane, this route typically takes 4h 05m.
When did momondo last update prices for flights from San Jose Airport to Chicago?
Prices for flights from San Jose Airport to Chicago are updated daily.
How many operators does momondo search for flights from San Jose Airport to Chicago?
As of March 2025, there are 7 operators available to choose from for flights from San Jose Airport to Chicago.
How old do you have to be to fly from San Jose Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San Jose Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago 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 Chicago. 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 San Jose to Chicago?
Based on momondo bookings for flights between San Jose and Chicago, the leading plane model is Boeing 737 MAX 8, making up 11.02% of the total bookings. Other popular models include Boeing 737-800 with 8.47%, Airbus A319 with 8.19%, and Boeing 777 with 7.49%.
What is the most popular airline from San Jose to Chicago?
momondo data reveals that the most frequently booked airline on the route from San Jose to Chicago is United Airlines, representing 47% of all bookings. The subsequent popular airlines are Spirit Airlines at 19%, Southwest at 12%, and Frontier at 12%.
Best airlines flying from San Jose to Chicago
Compare and see reviews for airlines that fly from San Jose to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $98 | Free Cancellation | Rating 6.0 3,318 reviews | |||
| PriceFrom $100 | Free Cancellation | Rating 8.0 9,713 reviews | |||
| PriceFrom $134 | Free Cancellation | Rating 6.3 7,940 reviews | |||
| PriceFrom $203 | Free Cancellation | Rating 7.4 8,679 reviews | |||
| PriceFrom $236 | Free Cancellation | Rating 8.0 8,070 reviews | |||
| PriceFrom $286 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $376 | Free Cancellation | Rating 8.1 4,333 reviews |
Southwest Flights From San Jose to Chicago
Southwest operates around 2 flights from San Jose to Chicago every week. The average price of these flights found in the last 72 hours has been $514, but momondo users have found Southwest deals from San Jose to Chicago from as low as $376 round-trip. Southwest has been scored 8.1/10 in 4,333 reviews.
United Airlines Flights From San Jose to Chicago
The best United Airlines deal for San Jose to Chicago flight tickets found on momondo in the last 72 hours was $203, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $512 round-trip. United Airlines operates 4 flights out of San Jose into Chicago in an average week, so prices vary by time and availability. 8,679 United Airlines reviews by users on momondo have scored the airline at 7.4/10.
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Why should I use momondo to find a flight deal from San Jose to Chicago?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from San Jose to Chicago. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from San Jose to Chicago with flexible booking policies on momondo?
Flights from San Jose to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from San Jose to Chicago?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from San Jose to Chicago.
I’m not ready to book a flight from San Jose to Chicago right now. Can momondo alert me if prices change?
If you are not ready to book a flight from San Jose to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.