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 CA $409 round trip and CA $182 one way. Prices and availability subject to change. Additional terms may apply.

Fri, Sep. 19 - Sun, Sep. 21
MDW
Chicago
SAN
San Diego
CA $409 Roundtrip, found 1 day ago
CA $409
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Sep. 19 from Chicago to San Diego, returning Sun, Sep. 21, priced at CA $409 found 1 day ago
Fri, Sep. 19 - Sun, Sep. 21
MDW
Chicago
SAN
San Diego
CA $457 Roundtrip, found 1 day ago
CA $457
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Sep. 19 from Chicago to San Diego, returning Sun, Sep. 21, priced at CA $457 found 1 day ago
Fri, Sep. 19 - Sun, Sep. 21
MDW
Chicago
SAN
San Diego
CA $471 Roundtrip, found 1 day ago
CA $471
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Sep. 19 from Chicago to San Diego, returning Sun, Sep. 21, priced at CA $471 found 1 day ago
Fri, Sep. 19 - Sun, Sep. 21
MDW
Chicago
SAN
San Diego
CA $522 Roundtrip, found 1 day ago
CA $522
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Sep. 19 from Chicago to San Diego, returning Sun, Sep. 21, priced at CA $522 found 1 day ago
Fri, Sep. 19 - Sun, Sep. 21
MDW
Chicago
SAN
San Diego
CA $534 Roundtrip, found 1 day ago
CA $534
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Sep. 19 from Chicago to San Diego, returning Sun, Sep. 21, priced at CA $534 found 1 day ago
Fri, Sep. 19 - Sun, Sep. 21
MDW
Chicago
SAN
San Diego
CA $583 Roundtrip, found 1 day ago
CA $583
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Sep. 19 from Chicago to San Diego, returning Sun, Sep. 21, priced at CA $583 found 1 day ago
Fri, Sep. 19 - Sun, Sep. 21
MDW
Chicago
SAN
San Diego
CA $586 Roundtrip, found 1 day ago
CA $586
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Sep. 19 from Chicago to San Diego, returning Sun, Sep. 21, priced at CA $586 found 1 day ago
Fri, Sep. 19 - Sun, Sep. 21
MDW
Chicago
SAN
San Diego
CA $598 Roundtrip, found 1 day ago
CA $598
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Sep. 19 from Chicago to San Diego, returning Sun, Sep. 21, priced at CA $598 found 1 day ago

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.

Popular Flight Routes from Chicago (MDW)

Travelers at MDW love to visit these top cities. Roam to the top destinations from Chicago (MDW) today with the cheap prices from Travelocity!

Popular Flight Routes from San Diego (SAN)

Travelers at SAN love to visit these top cities. Roam to the top destinations from San Diego(SAN) today with the cheap prices from Travelocity!

*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.