$106 Cheap Flights from Chicago (ORD) to San Diego (SAN)

You can find cheap one-way flights from $106 and cheap return flights from $180 Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.) with Expedia. One-way flights usually range from $128 to $931, and return flights typically cost between $255 and $2070. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.

September is typically the cheapest month to fly from Chicago (ORD) to San Diego (SAN), with average return fares around $245. This price is about 25% lower than the average throughout the year, as September follows the busy summer travel season when demand decreases. Other cheap months to fly from Chicago to San Diego include August and October.*Averages based on flights available on Expedia in the last year.

There are 3 airlines offering direct flights from ORD to SAN:

• United operates around 48 direct flights from ORD to SAN every week
• American Airlines operates around 30 direct flights from ORD to SAN every week
• Hawaiian Airlines operates around 13 direct flights from ORD to SAN every week

Sun Country Airlines is one of the cheapest airlines offering connecting flights from Chicago (ORD-O'Hare Intl.) to San Diego (SAN-San Diego Intl.), with round-trip tickets starting from around $192. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.

The best time to fly from Chicago (ORD) to San Diego (SAN) is in September or October. Average return flight prices are around $245, and these months provide pleasant weather in San Diego, making it an ideal time for a getaway.*Prices based on flights available on Expedia in the last year.

First class is available on flights from ORD to SAN. First class cabins are available on:

• United Airlines
• American Airlines
• Delta Air Lines
• Spirit Airlines

A direct, return business class ticket from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.) typically costs between $1,300 - $1,826. A non-stop, one-way business class flight is usually around $655 - $917. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.) if you opt for a connecting flight.*Prices based on flights available on Expedia in the last year.

It's easy to earn miles on a Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.