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

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Find The Best Dates To Fly

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

The cheapest flights to San Diego Intl. found within the past 7 days were CA $444 round trip and CA $223 one way. Prices and availability subject to change. Additional terms may apply.

Wed, Jan 14 - Thu, Jan 15
MDW
Chicago
SAN
San Diego
CA $444 Roundtrip, found 6 days ago
CA $444
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 14 from Chicago to San Diego, returning Thu, Jan 15, priced at CA $444 found 6 days ago
Wed, Jan 14 - Thu, Jan 15
MDW
Chicago
SAN
San Diego
CA $474 Roundtrip, found 6 days ago
CA $474
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 14 from Chicago to San Diego, returning Thu, Jan 15, priced at CA $474 found 6 days ago
Wed, Jan 14 - Thu, Jan 15
MDW
Chicago
SAN
San Diego
CA $516 Roundtrip, found 6 days ago
CA $516
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 14 from Chicago to San Diego, returning Thu, Jan 15, priced at CA $516 found 6 days ago
Wed, Jan 14 - Thu, Jan 15
MDW
Chicago
SAN
San Diego
CA $571 Roundtrip, found 6 days ago
CA $571
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 14 from Chicago to San Diego, returning Thu, Jan 15, priced at CA $571 found 6 days ago
Wed, Jan 14 - Thu, Jan 15
MDW
Chicago
SAN
San Diego
CA $599 Roundtrip, found 6 days ago
CA $599
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 14 from Chicago to San Diego, returning Thu, Jan 15, priced at CA $599 found 6 days ago
Wed, Jan 14 - Thu, Jan 15
MDW
Chicago
SAN
San Diego
CA $629 Roundtrip, found 6 days ago
CA $629
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 14 from Chicago to San Diego, returning Thu, Jan 15, priced at CA $629 found 6 days ago
Wed, Jan 14 - Thu, Jan 15
MDW
Chicago
SAN
San Diego
CA $643 Roundtrip, found 6 days ago
CA $643
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 14 from Chicago to San Diego, returning Thu, Jan 15, priced at CA $643 found 6 days ago
Wed, Jan 14 - Thu, Jan 15
MDW
Chicago
SAN
San Diego
CA $671 Roundtrip, found 6 days ago
CA $671
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 14 from Chicago to San Diego, returning Thu, Jan 15, priced at CA $671 found 6 days ago
Wed, Jan 14 - Thu, Jan 15
MDW
Chicago
SAN
San Diego
CA $727 Roundtrip, found 6 days ago
CA $727
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 14 from Chicago to San Diego, returning Thu, Jan 15, priced at CA $727 found 6 days ago
Wed, Jan 14 - Thu, Jan 15
MDW
Chicago
SAN
San Diego
CA $756 Roundtrip, found 6 days ago
CA $756
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 14 from Chicago to San Diego, returning Thu, Jan 15, priced at CA $756 found 6 days ago
Wed, Jan 14 - Thu, Jan 15
MDW
Chicago
SAN
San Diego
CA $798 Roundtrip, found 6 days ago
CA $798
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 14 from Chicago to San Diego, returning Thu, Jan 15, priced at CA $798 found 6 days ago
Wed, Jan 14 - Thu, Jan 15
MDW
Chicago
SAN
San Diego
CA $824 Roundtrip, found 6 days ago
CA $824
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 14 from Chicago to San Diego, returning Thu, Jan 15, priced at CA $824 found 6 days ago
Wed, Jan 14 - Thu, Jan 15
MDW
Chicago
SAN
San Diego
CA $825 Roundtrip, found 6 days ago
CA $825
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 14 from Chicago to San Diego, returning Thu, Jan 15, priced at CA $825 found 6 days ago
Wed, Jan 14 - Thu, Jan 15
MDW
Chicago
SAN
San Diego
CA $882 Roundtrip, found 6 days ago
CA $882
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 14 from Chicago to San Diego, returning Thu, Jan 15, priced at CA $882 found 6 days 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.