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Cheap SAN to MDW Flights

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

Chicago

$161.58

Cheap SAN to MDW Flights

Question : What is the cheapest day to fly?
Answer : The cheapest day to fly from San Diego to Chicago is on Friday. So, if you are trying to save a little cash on your next flight look for flights on that day.

Question : How much is a plane ticket to Chicago (MDW) from San Diego (SAN)?
Answer : Prices can range from $244 to $1,171. Booking in advance can usually help you get the cheapest price. However, usually the sooner you book, the better price you get.

Question : How many flights are there per day from San Diego to Chicago?
Answer : Depending on the day of the week, the number of flight times will change, but on average there are seven. The average route departing the United States currently has nine different flight times per day, so expect fewer options than you're used to.

Question : Is there an alternative airport near Chicago?
Answer : Fortunately for you, there is another one near Chicago. O'Hare International Airport (ORD) is 16 miles away, and over the next two months flights are being booked 42% cheaper than flights to Chicago Midway International Airport.

Question : Which airline has the least delays from San Diego to Chicago?
Answer : Booking with Delta Air Lines means you will arrive to Chicago around the time you were supposed to. In fact, this timely airline has a 100% average for landing before the plane turns into a pumpkin. It never hurts to be prepared. If you should choose this airline, be sure to track the flight status to stay on top of the departure time.

Question : Do some days of the week have more flight times than others?
Answer : With 10 total flight time options, Saturday provides the most flexibility from SAN to MDW. Thursday currently offers the least amount of flight times with only five options.

Question : How long is the flight from SAN to MDW?
Answer : This direct flight will whoosh you away to your destination in three hours and 45 minutes via Southwest Airlines. If you catch the 2:25 PM PST departure, you'll arrive at 8:10 PM CST. You'll have plenty of time to freshen up or grab a quick lunch (remember, there is a two-hour time difference).

San Diego to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from San Diego to Chicago will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with SAN to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind San Diego for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to MDW with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.