Cheap Flight Tickets from Chicago (MDW) to San Diego (SAN), Starting at $309

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

$314

WN Southwest Airlines • nonstop • 6h 55m

Sep 25 – Sep 27

The cheapest round trip flight from Chicago to San Diego (MDW-SAN-MDW) is currently $314

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Cheapest Direct Flight

$309

WN Southwest Airlines • nonstop • 7h 5m

Dec 25

The cheapest nonstop flight from Chicago to San Diego (MDW-SAN) is currently $309

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Fastest Flight

6h 45m

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

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 25 - Sep 27, Economy
WN
Chicago → San Diego
6h 55m
8:45 PM - 11:00 PM • nonstop
WN
Chicago → San Diego
6h 40m
6:20 AM - 12:20 PM • nonstop
$314
Southwest Airlines
Sep 25 - Sep 27, Economy
WN
Chicago → San Diego
6h 50m
10:15 AM - 12:25 PM • nonstop
WN
Chicago → San Diego
5h 50m
10:40 PM - 4:30 AM • nonstop
$314
Southwest Airlines
Sep 25 - Sep 27, Economy
WN
Chicago → San Diego
6h 55m
8:45 PM - 11:00 PM • nonstop
WN
Chicago → San Diego
10h
9:25 AM - 5:25 PM • 1 stop
$324
Southwest Airlines
Sep 25 - Sep 27, Economy
DL
Chicago → San Diego
12h 2m
6:05 AM - 11:27 AM • 1 stop
DL
Chicago → San Diego
10h 19m
1:36 PM - 9:55 PM • 1 stop
$448
Delta Airlines
Sep 25 - Sep 27, Economy
DL
Chicago → San Diego
10h 40m
9:29 AM - 2:09 PM • 1 stop
DL
Chicago → San Diego
10h 19m
1:36 PM - 9:55 PM • 1 stop
$448
Delta Airlines
Sep 25 - Sep 27, Economy
DL
Chicago → San Diego
10h 33m
7:13 PM - 11:46 PM • 1 stop
DL
Chicago → San Diego
10h 31m
3:00 PM - 11:31 PM • 1 stop
$448
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 6:05 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 314
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 8:55 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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