$75 Cheap Flights from Chicago (MDW) to San Diego (SAN)

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

Prices were available within the past 7 days and start at $75 for one-way flights and $124 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Flights from Chicago (MDW) to San Diego (SAN)
Origin airport
Midway Intl.
Destination airport
San Diego Intl.
Airlines serving
Delta, Frontier Airlines
Roundtrip price
$124
Distance
1725 mi
Average flight time
3 hours 4 mins

Chicago to San Diego Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Chicago to San Diego offer the perfect respite. Not only does exploring San Diego provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Chicago to San Diego may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from MDW to SAN today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of San Diego are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to San Diego more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to San Diego is $75 now!

Frequently asked questions

How much is a flight from Midway Airport to San Diego Airport?
If you’re traveling between Chicago Airport and San Diego Intl. Airport (SAN), round-trip flights start from $124. 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 1740 mi. 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.
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