£116 Cheap Flights from San Jose (SJC) to Chicago (ORD)

View £116 flight on Wed, 3 Jun 2026Opens in a new window

Popular airlines from Norman Y. Mineta San Jose Intl. Airport (SJC) to Chicago O'Hare International Airport (ORD)

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Cheap Flights from San Jose (SJC) to Chicago (ORD)

Prices were available within the past 7 days and start at £116 for one-way flights and £275 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Sat, 11 Jul - Sat, 18 Jul
SJC
San Jose
ORD
Chicago
£275 Return, found 2 days ago
£275
Return
found 2 days ago
Select Alaska Airlines flight, departing Sat, 11 Jul from San Jose to Chicago, returning Sat, 18 Jul, priced at £275 found 2 days ago
Alaska Airlines
Wed, 17 Jun - Wed, 24 Jun
SJC
San Jose
ORD
Chicago
£293 Return, found 17 hours ago
£293
Return
found 17 hours ago
Select Alaska Airlines flight, departing Wed, 17 Jun from San Jose to Chicago, returning Wed, 24 Jun, priced at £293 found 17 hours ago
Alaska Airlines
Wed, 17 Jun - Wed, 24 Jun
SJC
San Jose
ORD
Chicago
£308 Return, found 17 hours ago
£308
Return
found 17 hours ago
Select Alaska Airlines flight, departing Wed, 17 Jun from San Jose to Chicago, returning Wed, 24 Jun, priced at £308 found 17 hours ago
Alaska Airlines
Fri, 12 Jun - Fri, 19 Jun
SJC
San Jose
ORD
Chicago
£313 Return, found 17 hours ago
£313
Return
found 17 hours ago
Select Alaska Airlines flight, departing Fri, 12 Jun from San Jose to Chicago, returning Fri, 19 Jun, priced at £313 found 17 hours ago
Alaska Airlines
Sat, 16 May - Tue, 19 May
SJC
San Jose
ORD
Chicago
£318 Return, found 5 days ago
£318
Return
found 5 days ago
Select Alaska Airlines flight, departing Sat, 16 May from San Jose to Chicago, returning Tue, 19 May, priced at £318 found 5 days ago
Alaska Airlines
Wed, 17 Jun - Wed, 24 Jun
SJC
San Jose
ORD
Chicago
£330 Return, found 17 hours ago
£330
Return
found 17 hours ago
Select Alaska Airlines flight, departing Wed, 17 Jun from San Jose to Chicago, returning Wed, 24 Jun, priced at £330 found 17 hours ago
Alaska Airlines
Sat, 16 May - Tue, 19 May
SJC
San Jose
ORD
Chicago
£331 Return, found 5 days ago
£331
Return
found 5 days ago
Select Alaska Airlines flight, departing Sat, 16 May from San Jose to Chicago, returning Tue, 19 May, priced at £331 found 5 days ago
Alaska Airlines
Wed, 17 Jun - Wed, 24 Jun
SJC
San Jose
ORD
Chicago
£332 Return, found 17 hours ago
£332
Return
found 17 hours ago
Select Alaska Airlines flight, departing Wed, 17 Jun from San Jose to Chicago, returning Wed, 24 Jun, priced at £332 found 17 hours ago
Alaska Airlines
Sat, 11 Jul - Sat, 18 Jul
SJC
San Jose
ORD
Chicago
£334 Return, found 2 days ago
£334
Return
found 2 days ago
Select Alaska Airlines flight, departing Sat, 11 Jul from San Jose to Chicago, returning Sat, 18 Jul, priced at £334 found 2 days ago
Alaska Airlines
Sat, 16 May - Tue, 19 May
SJC
San Jose
ORD
Chicago
£337 Return, found 5 days ago
£337
Return
found 5 days ago
Select Alaska Airlines flight, departing Sat, 16 May from San Jose to Chicago, returning Tue, 19 May, priced at £337 found 5 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from £318
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from £318

Frequently asked questions

How much does a flight from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
One-way flights typically cost between £328 and £1,321 and return flights often range between £328 and £1,321. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Anaa (AAA) to Toronto, ON (YYZ-Pearson Intl.) ticket fares go up or down.
What is the cheapest month to fly from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
September is typically the cheapest month to fly from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.), with average return fares of approximately £526. This is about 18% lower than the average price throughout the year. September often sees lower prices as the summer travel rush ends and before the holiday season begins, leading to reduced demand. Other cheap months to fly from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) include May and August.
Which airlines fly direct from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Enter SJC to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) will differ from traveller to traveller. If you like to fly early, UA offers early morning flights. If price is the most important factor, AA typically offers the lowest fares. AS offers the most daily flights from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.), which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Based on booking data from the past year, the best time to fly from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) depends on what you're looking for. If you're seeking the lowest fares, September and August are typically the cheapest months, with average return flights around £526. However, if you prefer to travel when there are plenty of flight options and higher demand, July and January are the most popular months. Since there isn't an overlap between the cheapest and most popular months, you can choose to prioritize either cost savings in late summer or a wider selection of flights during peak travel times.
How many flights per day from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are approximately 2 nonstop flights per day from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.). For even more choice, look at flights that include layovers, as there are around 52 connecting flights per day. Some common connection points include Seattle - Tacoma Intl. (SEA), San Diego Intl. (SAN), and Sky Harbor Intl. (PHX).
What is the earliest flight from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically departs at approximately 5:05 AM local time. This service is operated by American Airlines and is seasonal, active only in May. An early departure like this can help you maximise your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You'll typically find the most flights from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) on a Friday, with around 45 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include Alaska Airlines, Southwest Airlines, and Delta Air Lines. Flight schedules are consistent throughout the week, with Friday having only slightly more flights than other weekdays.
What are the most popular departure times for flights from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) are in the early morning, from 6am to 9am. Approximately 37% of passengers prefer this time window. Many major carriers, including Southwest Airlines, United Airlines and American Airlines, offer flights during this window. Many travelers prefer these early flights to arrive at their destination with plenty of time for their day.
How long does it take to fly from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A nonstop flight from SJC to ORD typically takes around 4 hours 30 minutes, covering approximately 1,825 miles. Connecting flights on this route usually add 3 hours 50 minutes to your travel time. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Select the "Business class" and "First class" filters when looking for SJC to ORD flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Norman Y. Mineta San Jose Intl. (SJC)?
When traveling from Norman Y. Mineta San Jose Intl. (SJC) to Chicago, you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD). Some flights may connect through major hubs like McCarran Intl. (LAS), San Diego Intl. (SAN), Los Angeles Intl. (LAX) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Norman Y. Mineta San Jose Intl.
Destination airport
O'Hare Intl.
Return price
£275
Distance
2919 km
Average flight time
7 hours 11 mins

Book with confidence

Compare flights from San Jose to Chicago easily and book with confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from San Jose to Chicago. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to O'Hare Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Norman Y. Mineta San Jose Intl. to O'Hare Intl..  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from Norman Y. Mineta San Jose Intl. (SJC) to O'Hare Intl. (ORD)

The easiest way to view the best deals on flights from San Jose to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from Norman Y. Mineta San Jose Intl. to O'Hare Intl. start at just £275 and range up to £337.  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near San Jose and Chicago
  • booking your flight during July, the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your San Jose to Chicago flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Norman Y. Mineta San Jose Intl. to O'Hare Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

Compare flights from San Jose to Chicago easily and book with confidence

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*Available to Expedia members.