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£97 Cheap Flights from San Jose (SJC) to Chicago (ORD)

View £97 flight on Mon, 2 Nov 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 £97 for one-way flights and £193 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Tue, 15 Sept - Sat, 19 Sept
SJC
San Jose
ORD
Chicago
£193 Return, found 3 days ago
£193
Return
found 3 days ago
Select American Airlines flight, departing Tue, 15 Sept from San Jose to Chicago, returning Sat, 19 Sept, priced at £193 found 3 days ago
Alaska Airlines
Tue, 22 Sept - Thu, 24 Sept
SJC
San Jose
ORD
Chicago
£193 Return, found 3 days ago
£193
Return
found 3 days ago
Select Alaska Airlines flight, departing Tue, 22 Sept from San Jose to Chicago, returning Thu, 24 Sept, priced at £193 found 3 days ago
Alaska Airlines
Tue, 15 Sept - Sat, 19 Sept
SJC
San Jose
ORD
Chicago
£201 Return, found 3 days ago
£201
Return
found 3 days ago
Select Alaska Airlines flight, departing Tue, 15 Sept from San Jose to Chicago, returning Sat, 19 Sept, priced at £201 found 3 days ago
Alaska Airlines
Wed, 23 Sept - Sat, 26 Sept
SJC
San Jose
ORD
Chicago
£208 Return, found 3 days ago
£208
Return
found 3 days ago
Select Alaska Airlines flight, departing Wed, 23 Sept from San Jose to Chicago, returning Sat, 26 Sept, priced at £208 found 3 days ago
Delta
Wed, 9 Sept - Wed, 16 Sept
SJC
San Jose
ORD
Chicago
£217 Return, found 3 days ago
£217
Return
found 3 days ago
Select Delta flight, departing Wed, 9 Sept from San Jose to Chicago, returning Wed, 16 Sept, priced at £217 found 3 days ago
Alaska Airlines
Wed, 23 Sept - Sat, 26 Sept
SJC
San Jose
ORD
Chicago
£223 Return, found 3 days ago
£223
Return
found 3 days ago
Select Alaska Airlines flight, departing Wed, 23 Sept from San Jose to Chicago, returning Sat, 26 Sept, priced at £223 found 3 days ago
Alaska Airlines
Wed, 9 Sept - Wed, 16 Sept
SJC
San Jose
ORD
Chicago
£228 Return, found 3 days ago
£228
Return
found 3 days ago
Select Alaska Airlines flight, departing Wed, 9 Sept from San Jose to Chicago, returning Wed, 16 Sept, priced at £228 found 3 days ago
Alaska Airlines
Fri, 11 Sept - Fri, 18 Sept
SJC
San Jose
ORD
Chicago
£231 Return, found 1 day ago
£231
Return
found 1 day ago
Select Alaska Airlines flight, departing Fri, 11 Sept from San Jose to Chicago, returning Fri, 18 Sept, priced at £231 found 1 day ago
Delta
Wed, 19 Aug - Wed, 26 Aug
SJC
San Jose
ORD
Chicago
£232 Return, found 4 days ago
£232
Return
found 4 days ago
Select Delta flight, departing Wed, 19 Aug from San Jose to Chicago, returning Wed, 26 Aug, priced at £232 found 4 days ago
United
Tue, 15 Sept - Sat, 19 Sept
SJC
San Jose
ORD
Chicago
£254 Return, found 3 days ago
£254
Return
found 3 days ago
Select United flight, departing Tue, 15 Sept from San Jose to Chicago, returning Sat, 19 Sept, priced at £254 found 3 days ago

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city centre is 16 minutes. Flights from £477
MDW
Midway Intl.
CheapestClosest
Average driving time to city centre16 min
Flights from £477

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?
You can find one-way and return flights from SJC to ORD with Expedia. 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 our cheapest fares first, and use the Price Tracking tool to receive alerts when SJC to ORD 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.)?
If you're looking for the cheapest time to fly from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.), September is typically your best bet. You can expect average return fares around £283 during this month. September often sees lower prices as the summer travel rush winds down and before the holiday season picks up, making it a great time to find deals. Other budget-friendly months for this route include May and August.
Which airlines fly direct from San Jose, CA (SJC) to Chicago, IL (ORD)?
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) to Chicago, IL (ORD)?
To find a cheap flight from San Jose, CA (SJC) to Chicago, IL (ORD), 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 time to fly from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The cheapest months to fly from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) are typically September and August, with average return flights around £283. These months can offer a good balance of more affordable fares before the peak holiday travel season, giving you a chance to find excellent flight schedules that suit your plans.
What is the earliest flight from San Jose, CA (SJC) to Chicago, IL (ORD)?
Sort flights by "Departure (earliest)" on Expedia to find the earliest flight from San Jose, CA (SJC) to Chicago, IL (ORD). To compare more early flights, use the "Early Morning" and "Morning" filters in your search.
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.)?
Flying nonstop from SJC to ORD takes around 4 hours 20 minutes, with the route covering approximately 2,937 kilometers. Flights with a layover typically take 4 hours longer than direct options. 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) to Chicago, IL (ORD)?
Select the "Business class" and "First class" filters when looking for San Jose, CA (SJC) to Chicago, IL (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) to Chicago, IL (ORD) flight with Expedia?
It's easy to earn miles on a San Jose, CA (SJC) to Chicago, IL (ORD) 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.
Is it cheaper to buy a plane ticket from San Jose, CA (SJC) to Chicago, IL (ORD) at the last minute?
Typically, booking a last minute flight from San Jose, CA (SJC) to Chicago, IL (ORD) 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) to Chicago, IL (ORD) flight and hotel package?
Securing a San Jose, CA (SJC) to Chicago, IL (ORD) 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) to Chicago, IL (ORD)?
If you booked your San Jose, CA (SJC) to Chicago, IL (ORD) 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.
Airlines serving
Alaska Airlines
Return price
£193
Distance
2919 km
Average flight time
4 hours 24 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 £193 and range up to £254.  

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 September, 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.