Find United Airlines cheap flights from Chicago to San Diego. Enjoy a Chicago to San Diego modern flight experience in premium cabins with Wi-Fi.

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Our data shows that the cheapest route for a return flight from Chicago to San Diego cost $320 and was between Chicago O'Hare Intl Airport (ORD) and San Diego (SAN). On average, the best prices are found if you fly from Chicago Midway Airport (MDW) to San Diego (SAN).

Find the best deals on flights from Chicago O'Hare International (ORD) to San Diego International (SAN). Compare prices from hundreds of major travel agents and airlines, all in one search.

Looking for a cheap last-minute deal or the best round-trip flight from Chicago O'Hare International to San Diego? Find the lowest prices on one-way and round-trip tickets right here.

Each day, there are between 5 and 6 nonstop flights that take off from Chicago O'Hare Intl Airport and land in San Diego, with an average flight time of 4h 32m. The most common departure time is 4:00 pm and most flights take off in the afternoon. Each week, there are 39 flights.

Fly one-way from Chicago (Midway) to San Diego starting at $171. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

Each day, there are 2 nonstop flights that take off from Chicago Midway Airport and land in San Diego, with an average flight time of 4h 36m. The most common departure time is 8:00 am and most flights take off in the morning.

Cheap Flights from Chicago (CHI) to San Diego (SAN) start at $33 for one-way and $66 for round trip. Earn your airline miles on top of our rewards!