S$190 Cheap Flights from Chicago to San Diego

Airlines that fly from Chicago Midway Airport (MDW) to San Diego Intl. Airport (SAN)

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 40% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards

Cheap Flights from Chicago to San Diego (MDW-SAN)

Prices were available within the past 7 days and start at S$190 for one-way flights and S$407 for return, for the period specified. Prices and availability are subject to change. Additional terms apply.
Chicago to San Diego route information
Origin airport
Midway Intl.
Destination airport
San Diego Intl.
Return price
S$406
Distance
2761 km

Flights from Chicago to San Diego

When looking for plane tickets from Chicago to San Diego, the ease and convenience of using Expedia simply can’t be beat. With tons of departure points and flights options from the top airline carriers, Expedia gives you the widest array of cheap flights to San Diego. Look for MDW to SAN airfare with the assurance that you have the largest online travel agency working for you.

Expedia lets you search across the largest number of airlines and San Diego flights, which means that you’ll be able to find a great flight deal at the perfect travel date and time. Our simple-to-use booking engine makes looking for terrific bargains easy and hassle-free; just enter your travel dates and departure city, and let Expedia do the rest! Adjust your travel dates and explore connecting flights to find an even better deal on your Chicago San Diego flight!

Browse through dozens of options and rest assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Chicago to San Diego trip. There’s simply no substitute for great prices suited to your travel needs and backed by excellent customer support.

Combine your San Diego flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from Chicago to San Diego with Expedia. Use us as your stop travel destination and have the confidence that you’re getting a bargain!

Frequently asked questions

How much is a flight from Midway Airport to San Diego Airport?
If you’re travelling between Chicago Airport and San Diego Intl. Airport (SAN), round-trip flights start from S$407. This price is based on fares available within the last 7 days on Expedia for flights departing within the next year, so don’t delay. Book now and save yourself money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from MDW to San Diego Airport?
This differs between air carriers, as each one has its own terms and conditions. Visit the Customer Service Portal, where you’ll find instructions on how to cancel online.
How do I find cheap flights from Midway Intl. Airport (MDW) to San Diego Intl. Airport (SAN) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for MDW to San Diego Airport flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from Midway Airport to San Diego Airport?
The flight distance from Chicago to San Diego is 2,800 kilometres. Pack yourself a snack, a drink and a laptop filled with movies. Keep yourself entertained and the hours will zip by.
Which airlines fly direct from Midway Airport to San Diego Airport?
Southwest Airlines (WN) will take you from Chicago Airport to SAN safely and comfortably. You can choose from 86 flights each month along this route.
Are Midway Intl. Airport (MDW) to SAN flight tickets cheaper when they're purchased at the last minute?
It is possible to score an amazing last-minute deal from MDW to San Diego Airport, but it’s also possible to miss out entirely! As many airlines advertise prices up to 12 months in advance, it’s worth keeping an eye on fares early and being ready to book when you see a good bargain. Expedia compares carrier prices and updates flight deals often, so you can rest assured you’re always seeing the latest offers.
Chicago Airports
*Available to Expedia members.