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MDW (Chicago) to SAN (San Diego) Flights $255.53

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Cheap MDW to SAN Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Chicago to San Diego (MDW to SAN)

Question : Is there a preferred airline for getting to San Diego International Airport (SAN) on time?
Answer : Executive Jet Management will have you to SAN on time 100% of the time. Spend as little time in an airport as necessary by flying with Executive Jet Management. Perfection is hard to come by, so hopefully it continues.

Question : Is there another way to get to San Diego International Airport (SAN) besides Chicago Midway International Airport (MDW)?
Answer : Chicago Midway International Airport is a great airport, but in getting you to San Diego, there is a cheaper option – O'Hare International Airport. It's just 16 miles away and flights are being booked 37% cheaper over the upcoming two months.

Question : How long does it take to get from MDW to SAN?
Answer : Southwest Airlines can get you there in four hours and 20 minutes. For example, if you were to leave Chicago at 1:00 PM CDT, you would arrive in San Diego at 3:20 PM PDT (remember, there is a time change of two hours).

Question : Do travelers from Chicago typically stay in San Diego for very long?
Answer : Over the next two months, passengers from MDW to SAN are planning on staying for five days on average.

Question : Looking for the cheapest flight over the next 30 days?
Answer : As of Jul 24th, the best day for deals to San Diego (SAN) is Aug 11th. It costs $201, which is 54% below this route's average price.

Question : Which airline is least likely to get you to SAN on time?
Answer : 100% of Delta Air Lines flights from Chicago Midway International Airport (MDW) to San Diego International Airport (SAN) are delayed. If you’re on Delta Air Lines, be sure to sign up for the delay notifications to stay up to date with your flight’s status.

Question : If having the most departure times is important to you, is there a particular day of the week that offers the most options?
Answer : The day with the most departure times for this route is Saturday with three options. Note that the day with the most flight time options for all flights departing from the United States is Sunday with 5,738.