Cheap Flight Tickets from Chicago (MDW) to San Diego (SAN), Starting at $437

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

$444

DL Delta Airlines • 1 stop • 10h 11m

Sep 18 – Sep 25

The cheapest round trip flight from Chicago to San Diego (MDW-SAN-MDW) is currently $444

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Cheapest Direct Flight

$437

UA United Airlines • nonstop • 6h 59m

Sep 18

The cheapest nonstop flight from Chicago to San Diego (MDW-SAN) is currently $437

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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

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

Aeromexico Airline (AM)

Aeromexico

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.

Sep 18 - Sep 25, Economy
DL
Chicago → San Diego
10h 11m
7:40 PM - 11:51 PM • 1 stop
F9
Chicago → San Diego
10h 35m
9:03 PM - 5:38 AM • 1 stop
$444
Delta Airlines
Sep 18 - Sep 25, Economy
WN
Chicago → San Diego
6h 45m
2:50 PM - 4:55 PM • nonstop
WN
Chicago → San Diego
9h 15m
10:30 AM - 6:25 PM • 1 stop
$445
Southwest Airlines
Sep 18 - Sep 25, Economy
WN
Chicago → San Diego
10h 5m
5:55 PM - 10:00 PM • 1 stop
WN
Chicago → San Diego
5h 55m
11:05 AM - 5:00 PM • nonstop
$445
Southwest Airlines
Sep 18 - Sep 25, Economy
WN
Chicago → San Diego
10h 25m
2:45 PM - 7:10 PM • 1 stop
WN
Chicago → San Diego
15h 40m
6:15 PM - 5:55 AM • 1 stop
$454
Southwest Airlines
Sep 18 - Sep 25, Economy
WN
Chicago → San Diego
10h 40m
5:40 AM - 10:20 AM • 1 stop
WN
Chicago → San Diego
10h 10m
10:40 PM - 6:50 AM • 1 stop
$537
Southwest Airlines
Sep 18 - Sep 25, Economy
WN
Chicago → San Diego
12h 25m
10:15 AM - 4:00 PM • 1 stop
WN
Chicago → San Diego
8h 45m
7:50 AM - 3:15 PM • 1 stop
$918
Southwest 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 5:40 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 445
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 7:45 pm

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

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