£132 Cheap Flights from San Jose (SJC) to Chicago (ORD)

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.

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.

Enter SJC to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.

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.

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.

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.

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.

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.

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.

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.

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.

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.