Cheap Flight Tickets from San Diego (SAN) to Chicago (MDW), Starting at $164

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 One way Flight

$164

WN Southwest Airlines • 1 stop • 20h 20m

Sep 02

The cheapest one way flight from San Diego to Chicago (SAN-MDW) is currently $164

🔍 Search Flights

Fastest Flight

10h 45m

The fastest nonstop flight from San Diego to Chicago (SAN-MDW) takes 10h 45m

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)

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?
NO
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 6:15 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 DL : USD 441
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 8:15 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

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

Why Fareleaders for SAN to MDW Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on San Diego to Chicago flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on SAN to MDW flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of San Diego to Chicago 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 San Diego (SAN) to Chicago (MDW)
Terms and Conditions*