There are most likely no direct flights on the Chicago — San Diego route
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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.
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There are most likely no direct flights on the Chicago — San Diego route
Chicago — San Diego
07/02/2026
Departure
Direct flight
AA2484
starting at $365
Chicago — San Diego
08/01/2026
Departure
Direct flight
WN4648
starting at $450
Chicago — San Diego
08/02/2026
Departure
Direct flight
WN3103
starting at $226
Chicago — San Diego
07/10/2026
Departure
Direct flight
UA2428
starting at $209
starting at $365
starting at $226
starting at $209
starting at $125
starting at $157
More than 5 airlines operate flights from Chicago to San Diego, including American Airlines, Southwest Airlines, United Airlines, Frontier Airlines, and Alaska Airlines. This is a popular route, so passengers can choose tickets based on budget and preferences. Ticket prices start from $125, 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 08/01/2026, is operated by Frontier Airlines and costs $125
The cheapest roundtrip flight from Chicago to San Diego departs on 08/23/2026, is operated by Frontier Airlines and costs $229
Fastest flight from Chicago to San Diego takes 4h 34m
There are direct flights on this route 4 days a week: Su, Th, Fr, and Sa
The distance between Chicago and San Diego is 2786km (1727 miles). There are 18 direct flights from Chicago to San Diego. The time difference between Chicago and San Diego is 2h. Flights from Chicago begin at 6:40 AM. The latest flight from Chicago departs at 9:00 PM
The cheapest flight ticket from Chicago to San Diego according to data for the last 48 hours costs $125
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: July, August.
The fastest flights from Chicago to San Diego start from 4 hours 34 minutes in the air.
The following airlines operate direct flights on the route Chicago — San Diego: American Airlines, Southwest Airlines, United Airlines
The cost of a one-way flight from Chicago to San Diego ranges from $131 (July 2026) to $151 (August 2026). On average, the ticket price is about $141–$151.
We couldn't find any special offers for flights from Chicago to San Diego
