$94 Cheap Flights from Chicago (MDW) to San Diego (SAN)

View $94 flight on Mon, May 12, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at $94 for one-way flights and $188 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sun, May 4 - Fri, May 9
MDW
Chicago
SAN
San Diego
$188 Roundtrip, found 5 hours ago
$188
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sun, May 4 from Chicago to San Diego, returning Fri, May 9, priced at $188 found 5 hours ago
Frontier Airlines
Sat, May 24 - Thu, Jun 5
MDW
Chicago
SAN
San Diego
$198 Roundtrip, found 5 hours ago
$198
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, May 24 from Chicago to San Diego, returning Thu, Jun 5, priced at $198 found 5 hours ago
Frontier Airlines
Thu, May 15 - Mon, May 19
MDW
Chicago
SAN
San Diego
$208 Roundtrip, just found
$208
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, May 15 from Chicago to San Diego, returning Mon, May 19, priced at $208 just found
Frontier Airlines
Sat, May 24 - Sun, May 25
MDW
Chicago
SAN
San Diego
$218 Roundtrip, found 3 hours ago
$218
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, May 24 from Chicago to San Diego, returning Sun, May 25, priced at $218 found 3 hours ago
Southwest Airlines
Sat, May 31 - Tue, Jun 3
MDW
Chicago
SAN
San Diego
$223 Roundtrip, found 2 days ago
$223
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, May 31 from Chicago to San Diego, returning Tue, Jun 3, priced at $223 found 2 days ago
Frontier Airlines
Mon, May 12 - Sun, May 18
MDW
Chicago
SAN
San Diego
$228 Roundtrip, just found
$228
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, May 12 from Chicago to San Diego, returning Sun, May 18, priced at $228 just found
Southwest Airlines
Tue, Jun 3 - Tue, Jun 3
MDW
Chicago
SAN
San Diego
$232 Roundtrip, found 6 days ago
$232
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Jun 3 from Chicago to San Diego, returning Tue, Jun 3, priced at $232 found 6 days ago
Frontier Airlines
Fri, May 30 - Tue, Jun 3
MDW
Chicago
SAN
San Diego
$233 Roundtrip, found 4 hours ago
$233
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Fri, May 30 from Chicago to San Diego, returning Tue, Jun 3, priced at $233 found 4 hours ago
Southwest Airlines
Sat, Jun 7 - Wed, Jun 11
MDW
Chicago
SAN
San Diego
$237 Roundtrip, found 2 hours ago
$237
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Sat, Jun 7 from Chicago to San Diego, returning Wed, Jun 11, priced at $237 found 2 hours ago
Frontier Airlines
Tue, Jun 3 - Tue, Jun 10
MDW
Chicago
SAN
San Diego
$238 Roundtrip, found 11 hours ago
$238
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Tue, Jun 3 from Chicago to San Diego, returning Tue, Jun 10, priced at $238 found 11 hours ago
Flights from Chicago (MDW) to San Diego (SAN)
Origin airport
Midway Intl.
Destination airport
San Diego Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$188
Distance
1725 mi

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 May. 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 $94 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.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to San Diego Intl. Airport (SAN) cost?
Snag cheap return flights starting at $203 from Midway Intl. Airport (MDW) to San Diego Intl. Airport (SAN). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and Frontier Airlines flight leaving MDW on May 24 2025 and touching down at SAN. The price was last updated on April 28 2025 and has not changed since.
What is the cheapest month to fly from MDW to SAN?
The cheapest flights from MDW to SAN are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 MDW to SAN?
Jet off from MDW to SAN with Southwest Airlines. This airline currently has the cheapest one-way ticket for this route, starting from $119. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on July 19 2025. Prices were last updated on April 28 2025 and have not changed since.
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.

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