$67 Cheap Flights from Chicago (MDW) to San Diego (SAN)

View $67 flight on Wed, Dec 10, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to San Diego Intl. Airport (SAN)

Cheap Flights from Chicago to San Diego (MDW-SAN)

Prices were available within the past 7 days and start at $67 for one-way flights and $104 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Jan 20 - Wed, Jan 28
MDW
Chicago
SAN
San Diego
$104 Roundtrip, found 3 days ago
$104
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Jan 20 from Chicago to San Diego, returning Wed, Jan 28, priced at $104 found 3 days ago
Southwest Airlines
Tue, Jan 20 - Wed, Jan 28
MDW
Chicago
SAN
San Diego
$129 Roundtrip, found 3 days ago
$129
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Jan 20 from Chicago to San Diego, returning Wed, Jan 28, priced at $129 found 3 days ago
Southwest Airlines
Wed, Nov 12 - Sun, Nov 16
MDW
Chicago
SAN
San Diego
$133 Roundtrip, just found
$133
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Nov 12 from Chicago to San Diego, returning Sun, Nov 16, priced at $133 just found
Southwest Airlines
Sat, Oct 25 - Mon, Oct 27
MDW
Chicago
SAN
San Diego
$143 Roundtrip, just found
$143
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Oct 25 from Chicago to San Diego, returning Mon, Oct 27, priced at $143 just found
Southwest Airlines
Tue, Nov 11 - Tue, Nov 18
MDW
Chicago
SAN
San Diego
$148 Roundtrip, found 1 hour ago
$148
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Tue, Nov 11 from Chicago to San Diego, returning Tue, Nov 18, priced at $148 found 1 hour ago
Frontier Airlines
Thu, Oct 23 - Mon, Oct 27
MDW
Chicago
SAN
San Diego
$151 Roundtrip, found 2 hours ago
$151
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Oct 23 from Chicago to San Diego, returning Mon, Oct 27, priced at $151 found 2 hours ago
Southwest Airlines
Sat, Oct 25 - Mon, Oct 27
MDW
Chicago
SAN
San Diego
$152 Roundtrip, just found
$152
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Oct 25 from Chicago to San Diego, returning Mon, Oct 27, priced at $152 just found
Southwest Airlines
Tue, Dec 9 - Sat, Dec 13
MDW
Chicago
SAN
San Diego
$153 Roundtrip, found 4 hours ago
$153
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Tue, Dec 9 from Chicago to San Diego, returning Sat, Dec 13, priced at $153 found 4 hours ago
Frontier Airlines
Fri, Oct 24 - Sat, Nov 1
MDW
Chicago
SAN
San Diego
$154 Roundtrip, just found
$154
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Oct 24 from Chicago to San Diego, returning Sat, Nov 1, priced at $154 just found
Southwest Airlines
Mon, Nov 17 - Sat, Nov 22
MDW
Chicago
SAN
San Diego
$155 Roundtrip, just found
$155
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, Nov 17 from Chicago to San Diego, returning Sat, Nov 22, priced at $155 just found

Find the cheapest month to fly from Chicago (MDW) to San Diego (SAN)

October is typically the cheapest month to fly

From $118 - $410 per traveler.

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to San Diego Intl. Airport (SAN) cost?
Snag a cheap one-way flight from $67 or cheap return flight from $104 from Midway Intl. Airport (MDW) to San Diego Intl. Airport (SAN) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to San Diego Intl. Airport (SAN)?
January is the cheapest month to fly from MDW to SAN. Avoiding peak travel times is often the key to scoring lower fares.
Which airlines fly direct from Midway Intl. Airport (MDW) to San Diego Intl. Airport (SAN)?
When heading out of Midway Intl. Airport (MDW), you can jump on a nonstop flight to San Diego Intl. Airport (SAN) with Southwest Airlines.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to San Diego Intl. Airport (SAN)?
Expedia's filter tool lets you easily compare different airlines, departure times and fares all in one place. Customize the search to your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest MDW to SAN flight.
How many flights per day from Midway Intl. Airport (MDW) to San Diego Intl. Airport (SAN)?
When jetting out of Midway Intl. Airport (MDW), you'll have a choice from an average of 2 daily direct flights to San Diego Intl. Airport (SAN).
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to San Diego Intl. Airport (SAN)?
The 8 AM departures from MDW to SAN are typically the busiest. These flights can come with a higher price due to their popularity. If you're looking to save, pick a less crowded time to fly.
What day of the week has the most flights from MDW to SAN?
Friday offers the most flights from Midway Intl. Airport (MDW) to San Diego Intl. Airport (SAN). Consider leaving on this day and you'll have the best chance of finding a departure that fits your schedule.
What is the earliest flight from Midway Intl. Airport (MDW) to San Diego Intl. Airport (SAN)?
The first flight of the day taking off from Midway Intl. Airport (MDW) is at around 8:30AM UTC-6. Catch this flight and you'll arrive at San Diego Intl. Airport (SAN) at approximately 11:10AM UTC-8. The total time in the air is 4h 40m.
How long does it take to fly from Midway Intl. Airport (MDW) to San Diego Intl. Airport (SAN)?
It takes around 4 hours and 35 minutes to fly the 1,750 mi from MDW to SAN.
What airline has the least delays from MDW to SAN?
Consider traveling with Southwest Airlines if you'd like to fly straight from Midway Intl. Airport (MDW) to San Diego Intl. Airport (SAN) without any delays. This carrier has the best track record for punctuality, with an on-time score of 80%. Want to be notified if anything changes? You can keep an eye on your flight status using the Expedia App.
What is the best time to fly from Midway Intl. Airport (MDW) to San Diego Intl. Airport (SAN)?
To arrive at San Diego Intl. Airport (SAN) on schedule, opt for a flight that takes off from Midway Intl. Airport (MDW) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for San Diego from Midway Intl. Airport (MDW)?
If you're taking a direct flight from Midway Intl. Airport (MDW) to San Diego, San Diego Intl. Airport (SAN) is the only airport you can land at.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to San Diego Intl. Airport (SAN) last-minute?
Waiting until right before your break to book your flight from MDW to SAN often results in higher prices. While you may find some last-minute deals, they aren't always guaranteed. Be flexible with your travel plans for a better chance of snagging a bargain.
Is it cheaper to book a MDW to SAN flight and hotel package?
You can save money by securing a MDW to SAN flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one convenient place. After choosing your ideal flights and accommodations, you can add extras like tours, activities and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to San Diego Intl. Airport (SAN)?
Generally, it's possible to cancel or reschedule your MDW to SAN flight. However, if it's been more than 24 hours since booking, additional fees may apply. Check your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
San Diego Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$104
Distance
1725 mi
Average flight time
2 hours 56 mins

Book with confidence

Book with confidence

Chicago to San Diego Flights

The cheapest times to fly from Chicago to San Diego

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to San Diego are during the month of January. You can find some of the cheapest flights from Chicago to San Diego with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to San Diego

Sunday is one of the best days to book for cheap flights from Chicago to San Diego: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to San Diego

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to San Diego in 2025. You can also book with separate airlines for your outbound and return journeys, from $67 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to San Diego flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to San Diego airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to San Diego Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.