Cheap Flights from Chicago (CHI) to San Diego (SAN)

Frequently Asked Questions

• What are the cheapest flights from Chicago to San Diego (CHI-SAN)?

  Based on Trip.com data, Frontier Airlines offers one-way fares as low as US$81 on Cheapest nonstop routes (e.g. ORD to SAN on Wed, May 20), while United Airlines offers Cheapest nonstop round-trips from US$214 departing on Thu, May 21 and returning on Mon, May 25.

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

  At the moment, you can catch a nonstop flight from Chicago to San Diego with the following airlines, including: Alaska 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 is a flight from Chicago to San Diego?

  It takes about 5 hours 2 minutes to fly from Chicago to San Diego.

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

  By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Chicago to San Diego 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 Chicago to San Diego?

  Based on Trip.com data in the past 4 weeks, there is 49 flight per week flying from Chicago to San Diego. You can check the weekly schedule for popular airlines on this route below: Alaska Airlines: S/M/-/W/T/F/S -- AS1470 (09:35)

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

  To find best deals on flights from Chicago to San Diego, 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 Wed, May 20, with one-way flights priced at just US$81.
  · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Alaska 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 San Diego travel is around July.
  · Get exclusive promo codes for Trip.com app users.

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

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

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

  After crunching the numbers on our May flight calendar, it's currently cheapest to fly from Chicago to San Diego on May 12, 2026 with American Airlines, with prices starting at US$144.

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

  You can land at any one of the following hubs in San Diego, with Chicago O'Hare International Airport to San Diego International Airport (ORD-SAN) is by far the most common option on this route: McClellan-Palomar Airport (CLD) Marine Corps Air Station Miramar (NKX) San Diego International Airport (SAN).

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

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

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

  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.