Cheap Flights From Midway Intl. (MDW) To San Diego Intl. (SAN)

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Cheapest Flights from Chicago (MDW) to San Diego (SAN)

The cheapest flights to San Diego Intl. found within the past 7 days were round trip and CA $186 one way. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Are there direct flights from Midway Intl. Airport (MDW) to San Diego Airport?
If you're not a huge fan of layovers, it's smart to arrange your flight from Chicago Airport to SAN in advance. Southwest Airlines is the only air carrier that operates nonstop flights on this route.
What airlines fly from Midway Airport to SAN?
With Southwest Airlines, you won't have to stress about annoying layovers or hanging around waiting for your connecting flight. This popular airline will fly you straight from Chicago to San Diego County on one of the 104 flights offered on this route every month.
What is the best day to buy a plane ticket?
Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you're looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you're browsing flight deals.
What are the cheapest days to fly?
Frequent travellers may already know this, but earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.
How far in advance can you book a flight?
Here's the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.