American Airlines
Su and Fr
starting at $305
Alaska Airlines
Su and Fr
starting at $89
Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from Chicago to San Diego. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
A non-stop flight is the most convenient and comfortable way to fly from Chicago to San Diego, despite the fact that sometimes flights with transfers can cost significantly less.
•
•
•
•
•
•
Answers to questions about the route that travelers are most interested in.
We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
American Airlines
Su and Fr
starting at $305
Alaska Airlines
Su and Fr
starting at $89
The airlines on the Chicago — San Diego route each fly on specific days: American Airlines and Alaska Airlines fly on Sunday and Friday.
Chicago — San Diego
09/10/2026
Departure
Direct flight
WN518
starting at $249
Chicago — San Diego
10/03/2026
Departure
Direct flight
AS1470
starting at $227
Chicago — San Diego
10/13/2026
Departure
Direct flight
AA1785
starting at $378
starting at $249
starting at $146
starting at $378
starting at $120
More than 4 airlines operate flights from Chicago to San Diego, including Southwest Airlines, Alaska Airlines, American Airlines, and Frontier Airlines. This is a popular route, so passengers can choose tickets based on budget and preferences. Ticket prices start from $120, and our service lets you instantly compare all options. The variety of offers simplifies planning: you can choose budget fares or more comfortable options with baggage included or extra services. We help you find the best deals so your trip is cost-efficient.
The cheapest one-way flight from Chicago to San Diego departs on 10/03/2026, is operated by Frontier Airlines and costs $120
The cheapest roundtrip flight from Chicago to San Diego departs on 09/22/2026, is operated by Alaska Airlines and costs $242
Fastest flight from Chicago to San Diego takes 4h 43m
There are direct flights on this route 3 days a week: Tu, Th, and Sa
The distance between Chicago and San Diego is 2786km (1727 miles). There are 137 direct flights from Chicago to San Diego. The time difference between Chicago and San Diego is 2h. Flights from Chicago begin at 5:45 AM. The latest flight from Chicago departs at 9:10 PM
We couldn't find any special offers for flights from Chicago to San Diego
The cheapest flight ticket from Chicago to San Diego according to data for the last 48 hours costs $120
Often the best time to buy tickets from Chicago to San Diego is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Chicago to San Diego can be found flying in these months: October, September.
The fastest flights from Chicago to San Diego start from 4 hours 43 minutes in the air.
The following airlines operate direct flights on the route Chicago — San Diego: Southwest Airlines, Alaska Airlines, American Airlines
The cost of a one-way flight from Chicago to San Diego ranges from $120 (October 2026) to $146 (September 2026). On average, the ticket price is about $133–$146.