Cheap Flights from San Jose to Chicago from $115

Frequently Asked Questions

• What are the cheapest flights from San Jose to Chicago (SJO-CHI)?

  Based on Trip.com data, Spirit Airlines offers one-way fares as low as $115 on Cheapest nonstop routes (e.g. SJO to ORD on Fri, Feb 13), while Spirit Airlines offers Cheapest nonstop round-trips from $296 departing on Thu, Feb 26 and returning on Sun, Mar 1.

• Which airlines offer direct 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: Volaris Costa Rica American Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.

• How long does it take to fly from San Jose (SJO) to Chicago (CHI) and what is the distance?

  It takes around 5 hours 28 minutes to fly from San Jose (SJO) to Chicago (CHI).

• When is the best time to book flights 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.

• How many flights are there per week from San Jose to Chicago?

  Based on Trip.com data in the past 4 weeks, there is 7 flight per week flying from San Jose to Chicago. You can check the weekly schedule for popular airlines on this route below: American Airlines: S/M/T/-/-/F/S -- AA314 (07:14)

• How can I find the best deals on flights from San Jose to Chicago?

  To find best deals on flights from San Jose to Chicago, you can use various tools on Trip.com:
  · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Fri, Feb 13, with one-way flights priced at just $115.
  · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is United Airlines.
  · Set up price alerts to easily monitor ticket prices without having to check every day.
  · Check Trip.com flight deals and promo codes frequently.
  · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around January.
  · Get exclusive promo codes for Trip.com app users.

• When are flight tickets from San Jose (SJO) to Chicago (CHI) the cheapest?

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

• Which upcoming date is cheapest to fly from San Jose to Chicago on?

  After crunching the numbers on our February flight calendar, it's currently cheapest to fly from San Jose to Chicago on February 13, 2026 with Spirit Airlines, with prices starting at $115.

• Which airports can I fly to for Chicago from San Jose?

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

• Is there any time difference between San Jose and Chicago?

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

• How do I change or cancel my ticket from San Jose to Chicago?

  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.