Cheap flight from San Diego to Chicago from $107

Frequently Asked Questions

• Which airlines offer direct flights from San Diego to Chicago?

  At the moment, you can catch a nonstop flight from San Diego to Chicago with the following airlines, including: Alaska Airlines Hawaiian Airlines United Airlines 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 Diego (SAN) to Chicago (CHI) and what is the distance?

  It takes around 4 hours 7 minutes to fly from San Diego (SAN) to Chicago (CHI).

• When is the best time to book flights from San Diego 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 Diego 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 Diego to Chicago?

  Based on Trip.com data in the past 4 weeks, there is 51 flight per week flying from San Diego to Chicago. You can check the weekly schedule for popular airlines on this route below: Alaska Airlines: S/M/T/W/T/F/S -- AS1446 (08:28) Hawaiian Airlines: S/M/T/W/T/F/S -- HA6535 (08:28)

• When are flight tickets from San Diego (SAN) to Chicago (CHI) the cheapest?

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

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

  After crunching the numbers on our November flight calendar, it's currently cheapest to fly from San Diego to Chicago on November 11, 2025 with Frontier Airlines, with prices starting at $117.

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

  You can land at any one of the following hubs in Chicago, with San Diego International Airport to O'Hare International Airport (SAN-ORD) 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 Diego and Chicago?

  The time difference between Chicago and San Diego is 2h.

• How do I change or cancel my ticket from San Diego 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.