Cheap Flight Tickets from San Diego (SAN) to Chicago (MDW), Starting at $200

Good to Know: Cheapest and Fastest SAN - MDW Flights

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

Cheapest Round Trip Flight

$270

WN Southwest Airlines • 1 stop • 7h 25m

Jul 03 – Jul 19

The cheapest round trip flight from San Diego to Chicago (SAN-MDW-SAN) is currently $270

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Cheapest Direct Flight

$200

WN Southwest Airlines • nonstop • 6h 40m

Jul 03

The cheapest nonstop flight from San Diego to Chicago (SAN-MDW) is currently $200

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Fastest Flight

5h 55m

The fastest nonstop flight from San Diego to Chicago (SAN-MDW) takes 5h 55m

Top Airlines Flying from San Diego to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

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

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

Jul 03 - Jul 19, Economy
WN
San Diego → Chicago
7h 25m
5:10 PM - 12:35 AM • 1 stop
WN
San Diego → Chicago
7h 30m
5:25 AM - 9:00 AM • 1 stop
$270
Southwest Airlines
Jul 03 - Jul 19, Economy
WN
San Diego → Chicago
7h 25m
1:50 PM - 9:15 PM • 1 stop
WN
San Diego → Chicago
7h 30m
5:25 AM - 9:00 AM • 1 stop
$296
Southwest Airlines
Jul 03 - Jul 19, Economy
WN
San Diego → Chicago
8h 40m
7:45 AM - 3:55 PM • 1 stop
WN
San Diego → Chicago
7h 30m
5:25 AM - 9:00 AM • 1 stop
$310
Southwest Airlines
Jul 03 - Jul 19, Economy
WN
San Diego → Chicago
10h 25m
9:45 AM - 6:10 PM • 1 stop
WN
San Diego → Chicago
6h 50m
6:10 AM - 8:20 AM • nonstop
$367
Southwest Airlines
Jul 03 - Jul 19, Economy
WN
San Diego → Chicago
8h 45m
9:45 PM - 5:10 AM • 1 stop
WN
San Diego → Chicago
6h 50m
6:10 AM - 8:20 AM • nonstop
$367
Southwest Airlines
Jul 03 - Jul 19, Economy
WN
San Diego → Chicago
14h 15m
8:40 PM - 7:35 AM • 1 stop
WN
San Diego → Chicago
9h
5:35 PM - 9:15 PM • 1 stop
$372
Southwest Airlines

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

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

FAQs on San Diego to Chicago Flights

What are the airports in San Diego?
SAN
What’s the most popular airline flying from SAN to MDW?
The most popular airline flying from San Diego to Chicago are
Can I fly from SAN to MDW non-stop?
Yes, you can fly SAN to MDW non-stop on
Which airlines fly nonstop between San Diego and Chicago?
The non-stop flights between San Diego and Chicago are .
What’s the earliest departure time from SAN to MDW Airport?
The earliest flight leaves SAN at 6:30 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my San Diego to Chicago 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 SAN to MDW?
Read the fare rules of the San Diego to Chicago 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 San Diego and Chicago?
operate flights between San Diego and Chicago
How long does a flight from San Diego to Chicago take?
It takes approximately 4 hour to fly non-stop from SAN to MDW, which is 1728.01 miles by air.
Which airlines provide the cheapest flights from San Diego (SAN) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from SAN were found on WN : USD 296
Do I need a passport to fly between SAN and MDW?
No
What’s the latest departure time from SAN to MDW ?
The last flight leaves SAN at 10:40 pm

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

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

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