Cheap Flight Tickets from Chicago (MDW) to San Diego (SAN), Starting at $392

Good to Know: Cheapest and Fastest MDW - SAN Flights

Useful information for finding best airline tickets from Chicago Midway International to San Diego International on your next trip.

Cheapest Round Trip Flight

$392

DL Delta Airlines • 1 stop • 13h 45m

Aug 10 – Aug 17

The cheapest round trip flight from Chicago to San Diego (MDW-SAN-MDW) is currently $392

🔍 Search Flights

Cheapest Direct Flight

$475

WN Southwest Airlines • nonstop • 6h 50m

Aug 10

The cheapest nonstop flight from Chicago to San Diego (MDW-SAN) is currently $475

🔍 Search Flights

Fastest Flight

6h 45m

The fastest nonstop flight from Chicago to San Diego (MDW-SAN) takes 6h 45m

Top Airlines Flying from Chicago to San Diego

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

Latest Flight Deals from Chicago (MDW) to San Diego (SAN)

Compare and book low fare round-trip air tickets from Chicago to San Diego. Ideal for travelers with confirmed return itineraries.

Aug 10 - Aug 17, Economy
DL
Chicago → San Diego
13h 45m
1:51 PM - 8:16 PM • 1 stop
DL
Chicago → San Diego
15h
10:17 PM - 9:17 AM • 1 stop
$392
Delta Airlines
Aug 10 - Aug 17, Economy
WN
Chicago → San Diego
6h 50m
10:15 AM - 12:25 PM • nonstop
WN
Chicago → San Diego
11h 50m
10:10 AM - 7:20 PM • 2 stops
$485
Southwest Airlines
Aug 10 - Aug 17, Economy
WN
Chicago → San Diego
9h 15m
6:40 AM - 10:35 AM • 1 stop
WN
Chicago → San Diego
5h 50m
10:40 PM - 4:30 AM • nonstop
$485
Southwest Airlines
Aug 10 - Aug 17, Economy
DL
Chicago → San Diego
20h 17m
9:59 AM - 8:16 PM • 1 stop
DL
Chicago → San Diego
15h
10:17 PM - 9:17 AM • 1 stop
$546
Delta Airlines
Aug 10 - Aug 17, Economy
DL
Chicago → San Diego
19h 19m
1:51 PM - 11:50 PM • 2 stops
DL
Chicago → San Diego
15h
10:17 PM - 9:17 AM • 1 stop
$550
Delta Airlines
Aug 10 - Aug 17, Economy
DL
Chicago → San Diego
17h 31m
1:25 PM - 10:16 PM • 1 stop
DL
Chicago → San Diego
15h 34m
10:25 PM - 9:59 AM • 1 stop
$564
Delta Airlines

Fly from Chicago to San Diego with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to San Diego? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Chicago to San Diego Flights

What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from MDW to SAN?
The most popular airline flying from Chicago to San Diego are
Can I fly from MDW to SAN non-stop?
Yes, you can fly MDW to SAN non-stop on
Which airlines fly nonstop between Chicago and San Diego?
The non-stop flights between Chicago and San Diego are .
What’s the earliest departure time from MDW to SAN Airport?
The earliest flight leaves MDW at 6:10 am and lands in SAN - San Diego International
What are the airports in San Diego?
SAN
Can I make changes to my Chicago to San Diego flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from MDW to SAN?
Read the fare rules of the Chicago to San Diego air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Chicago and San Diego?
operate flights between Chicago and San Diego
How long does a flight from Chicago to San Diego take?
It takes approximately 4 hour to fly non-stop from MDW to SAN, which is 1728.01 miles by air.
Which airlines provide the cheapest flights from Chicago (MDW) to San Diego (SAN) ?
In the past couple of days, the cheapest tickets to SAN from MDW were found on WN : USD 485
Do I need a passport to fly between MDW and SAN?
No
What’s the latest departure time from MDW to SAN ?
The last flight leaves MDW at 8:45 pm

Essential Information for Booking Flights from Chicago (MDW) - AI Insights

What's the cheapest airline from mdw to san?
You can find affordable Business class flights from Chicago Midway International Airport (mdw) to San Diego International Airport (san) on Southwest Airlines. The cheapest fares are usually available 19 days in advance, and booking a one-way trip can help you save money. With Southwest Airlines, you can enjoy priority check-in, lounge access, and flatbed seats for a comfortable Business class experience.
What's the popular airline to fly from mdw to san?
You can fly from Chicago Midway International Airport (mdw) to San Diego International Airport (san) on Southwest Airlines. This business class flight has one stop, is a one-way trip, and can be booked 19 days in advance for budget-friendly airfares. Low fares are available with this airline.
What's the cheapest day of the week to fly from mdw to san?
The cheapest day to fly from Chicago Midway International (mdw) to San Diego International (san) is Sunday. Flying on Sundays can result in lower fares, making it a budget-friendly option for your one-way trip. Consider booking your flight at least 19 days in advance to secure the best airfare savings.
What's the cheapest month to fly from mdw to san?
The cheapest month to fly from Chicago Midway International Airport (mdw) to San Diego International Airport (san) is November. Flying during this time can help you secure a budget-friendly Business class ticket, which often comes with priority check-in, lounge access, and flatbed seats.
Which airline/airlines fly from mdw to san?
Allegiant (G4), WestJet Airlines (WS), Porter Airline (PD), United Airlines (UA), American Airlines (AA), Aeromexico (AM), Hawaiian Airlines (HA), Air New Zealand (NZ), Delta Airlines (DL), and Frontier Airlines (F9) offer flights from Chicago Midway International Airport (mdw) to San Diego International Airport (san). You can find budget-friendly options with advance booking, such as 19 days in advance. For a business class ticket on this route, consider booking with airlines that cater to premium services.
What is the cheapest airline to fly from Chicago Midway International Airport to San Diego International Airport?
Southwest Airlines (WN) offers the best fares for this route.
Can I find the cheapest airfares on your website for July travel?
Yes, our website has the most affordable options for July flights.
Are there any discounts or promotions available for busco travelers?
We have exclusive deals for busco travelers, check our website for more information.
How far in advance can I book my flight for the best fares on Milwaukee flights?
Book your Milwaukee flight at least 19 days in advance to get the cheapest fares.
What is the most affordable way to book my trip with agencia?
Our website offers the best deals for agencia travelers, compare and book today.

Chicago (MDW) to San Diego (SAN): Airport Information

Origin Airport Chicago Midway International , Chicago, US
Destination Airport San Diego International , San Diego, US
Distance 1728 miles

More Flight Options for Chicago (MDW) and San Diego (SAN)

Why Fareleaders for MDW to SAN Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Chicago to San Diego flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on MDW to SAN flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Chicago to San Diego flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Chicago (MDW) to San Diego (SAN)
Terms and Conditions*