Find Spirit Airlines(NK) flights from San Jose to Chicago

At the moment, you can catch a nonstop flight from San Jose to Chicago with the following airlines, including: American Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.

It takes about 5 hours 35 minutes to fly from San Jose to Chicago.

By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from San Jose to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

Based on Trip.com data in the past 4 weeks, there is 1 flight per week flying from San Jose to Chicago. You can check the weekly schedule for popular airlines on this route below: American Airlines: -/-/-/-/-/-/- -- AA2824 (06:21)

The cheapest months to fly from San Jose to Chicago is September, when demand for travel is lower.

After crunching the numbers on our July flight calendar, it's currently cheapest to fly from San Jose to Chicago on July 23, 2026 with United Airlines, with prices starting at US$391.

You can land at any one of the following hubs in Chicago, with Juan Santamaría International Airport to O'Hare International Airport (SJO-ORD) is by far the most common option on this route: Chicago Midway International Airport (MDW) O'Hare International Airport (ORD) Chicago Rockford International Airport (RFD).

The time difference between Chicago and San Jose is 0h.

Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.