Cheap flights from San Jose to Chicago from $75
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 7/22. 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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Frontier flights from San Jose to Chicago O'Hare Intl Airport
Our best Frontier deals on San Jose to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines flights from San Jose to Chicago O'Hare Intl Airport
Our best Spirit Airlines deals on San Jose to Chicago O'Hare Intl Airport flight tickets
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How to get the cheapest flight ticket from San Jose to Chicago O'Hare Intl Airport
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 Chicago O'Hare Intl Airport?
The month of April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from San Jose averaging around $417.
What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?
The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Tuesday when prices can be found for as low as $471. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from San Jose because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $586.
What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?
Flying to Chicago O'Hare Intl Airport from San Jose in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $298 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $636. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest San Jose to Chicago O'Hare Intl flight route?
Fly from San Jose to Chicago O'Hare Intl for the best San Jose - Chicago O'Hare Intl flight prices
How far in advance should I book a flight to Chicago O'Hare Intl Airport?
You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from San Jose when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $460 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from San Jose for as low as $262 on momondo.
What cabin class options are available on San Jose to Chicago O'Hare Intl flights?
There are 4 cabin classes available to choose from on San Jose to Chicago O'Hare Intl 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 San Jose to Chicago O'Hare Intl Airport flights?
You could potentially save up to 19% on your flight if you consider stops on a San Jose to Chicago O'Hare Intl Airport flight.
How have San Jose to Chicago O'Hare Intl Airport flight prices changed over time?
As of July 2025, prices for San Jose to Chicago O'Hare Intl Airport flights are approximately 47% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from San Jose to Chicago O'Hare Intl?
Spirit Airlines, Frontier, and Hawaiian Airlines are the most popular carriers operating from San Jose to Chicago O'Hare Intl
What airlines fly to Chicago O'Hare Intl Airport?
United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport. Keep in mind that there are 8 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from San Jose to Chicago O'Hare Intl Airport on average per week?
5 flights are operational weekly from San Jose to Chicago O'Hare Intl Airport as of July 2025. The most popular departure day for this route is Mon, with 20% of flights per week taking off on this day.
When to book flights from San Jose to Chicago O'Hare Intl Airport
Cheap San Jose to Chicago O'Hare Intl Airport (SJC to ORD) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from San Jose to Chicago O'Hare Intl Airport
How far is San Jose to Chicago O'Hare Intl by plane?
The straight-line distance from San Jose to Chicago O'Hare Intl is 1822.3 mi. Flights usually cover this in 5h 43m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from San Jose Airport to Chicago O'Hare Intl Airport?
Prices for flights from San Jose Airport to Chicago O'Hare Intl Airport were last updated today.
How many operators does momondo search for flights from San Jose Airport to Chicago O'Hare Intl Airport?
As of July 2025, there are 7 operators available to choose from for flights from San Jose Airport to Chicago O'Hare Intl Airport.
How old do you have to be to fly from San Jose Airport to Chicago O'Hare Intl 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 San Jose Airport to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from San Jose to Chicago O'Hare Intl Airport?
Based on momondo bookings for flights between San Jose and Chicago O'Hare Intl Airport, the leading plane model is Airbus A320-100/200, making up 14.49% of the total bookings. Other popular models include Boeing 737 MAX 8 with 10.61%, Boeing 737 MAX 9 with 9.59%, and Boeing 777 with 7.76%.
What is the most popular airline from San Jose to Chicago O'Hare Intl Airport?
momondo data reveals that the most frequently booked airline on the route from San Jose to Chicago O'Hare Intl Airport is United Airlines, representing 62% of all bookings. The subsequent popular airlines are Spirit Airlines at 14%, Delta at 9%, and Southwest at 6%.
Best airlines flying from San Jose to Chicago O'Hare Intl Airport
Compare and see reviews for airlines that fly from San Jose to Chicago O'Hare Intl Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $98 | Free Cancellation | Rating 5.9 3,284 reviews | |||
| PriceFrom $108 | Free Cancellation | Rating 6.3 8,094 reviews | |||
| PriceFrom $170 | Free Cancellation | Rating 8.0 10,000 reviews | |||
| PriceFrom $200 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $236 | Free Cancellation | Rating 8.0 7,983 reviews | |||
| PriceFrom $333 | Free Cancellation | Rating 7.4 8,861 reviews | |||
| PriceFrom $370 | Free Cancellation | Rating 8.0 4,270 reviews |
United Airlines Flights From San Jose to Chicago O'Hare Intl Airport
United Airlines flies from San Jose to Chicago O'Hare Intl Airport around 5 times per week, with 8,861 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from San Jose to Chicago O'Hare Intl Airport in the last 72 hours was $333 (round-trip), much lower than the average airfare cost of $528 for United Airlines flights on this route.
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Why should I use momondo to find a flight deal from San Jose to Chicago?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from San Jose to Chicago for you.
Can I find flights from San Jose to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from San Jose with this policy.
How can momondo help me find flights from San Jose to Chicago?
momondo helps you find the best flight between San Jose and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
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 simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from San Jose and alert you when they change.