฿4,190 Cheap Flights from Chicago (MDW) to San Diego (SAN)

View ฿4,190 flight on Sat, 2 Aug 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to San Diego Intl. Airport (SAN)

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

Prices were available within the past 7 days and start at ฿4,190 for one-way flights and ฿8,380 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, 2 Aug - Sat, 9 Aug
MDW
Chicago
SAN
San Diego
฿8,380 Return, just found
฿8,380
Return
just found
Select Delta flight, departing Sat, 2 Aug from Chicago to San Diego, returning Sat, 9 Aug, priced at ฿8,380 just found
Delta
Tue, 29 Jul - Tue, 5 Aug
MDW
Chicago
SAN
San Diego
฿8,440 Return, found 4 days ago
฿8,440
Return
found 4 days ago
Select Delta flight, departing Tue, 29 Jul from Chicago to San Diego, returning Tue, 5 Aug, priced at ฿8,440 found 4 days ago
Delta
Tue, 29 Jul - Tue, 5 Aug
MDW
Chicago
SAN
San Diego
฿10,575 Return, found 4 days ago
฿10,575
Return
found 4 days ago
Select Delta flight, departing Tue, 29 Jul from Chicago to San Diego, returning Tue, 5 Aug, priced at ฿10,575 found 4 days ago
Delta
Sat, 2 Aug - Sat, 9 Aug
MDW
Chicago
SAN
San Diego
฿11,315 Return, just found
฿11,315
Return
just found
Select Delta flight, departing Sat, 2 Aug from Chicago to San Diego, returning Sat, 9 Aug, priced at ฿11,315 just found
Delta
Tue, 29 Jul - Tue, 5 Aug
MDW
Chicago
SAN
San Diego
฿11,390 Return, found 4 days ago
฿11,390
Return
found 4 days ago
Select Delta flight, departing Tue, 29 Jul from Chicago to San Diego, returning Tue, 5 Aug, priced at ฿11,390 found 4 days ago
Delta
Sat, 2 Aug - Sat, 9 Aug
MDW
Chicago
SAN
San Diego
฿12,325 Return, just found
฿12,325
Return
just found
Select Delta flight, departing Sat, 2 Aug from Chicago to San Diego, returning Sat, 9 Aug, priced at ฿12,325 just found
Delta
Tue, 29 Jul - Tue, 5 Aug
MDW
Chicago
SAN
San Diego
฿12,705 Return, found 4 days ago
฿12,705
Return
found 4 days ago
Select Delta flight, departing Tue, 29 Jul from Chicago to San Diego, returning Tue, 5 Aug, priced at ฿12,705 found 4 days ago
Delta
Wed, 2 Jul - Tue, 8 Jul
MDW
Chicago
SAN
San Diego
฿12,740 Return, found 2 days ago
฿12,740
Return
found 2 days ago
Select Delta flight, departing Wed, 2 Jul from Chicago to San Diego, returning Tue, 8 Jul, priced at ฿12,740 found 2 days ago
Delta
Wed, 2 Jul - Tue, 8 Jul
MDW
Chicago
SAN
San Diego
฿14,540 Return, found 2 days ago
฿14,540
Return
found 2 days ago
Select Delta flight, departing Wed, 2 Jul from Chicago to San Diego, returning Tue, 8 Jul, priced at ฿14,540 found 2 days ago
Delta
Wed, 2 Jul - Tue, 8 Jul
MDW
Chicago
SAN
San Diego
฿15,035 Return, found 2 days ago
฿15,035
Return
found 2 days ago
Select Delta flight, departing Wed, 2 Jul from Chicago to San Diego, returning Tue, 8 Jul, priced at ฿15,035 found 2 days ago

Find the cheapest month to fly from Chicago (MDW) to San Diego (SAN)

January is typically the cheapest month to fly

From ฿3,849 - ฿14,890 per traveller.

Graph displaying average flight prices per month

Flight from Chicago to San Diego route information
Origin airport
Midway Intl.
Destination airport
San Diego Intl.
Return price
฿8,380
Distance
2761 km
Average flight time
2 hours 23 mins

Perfect flights from Chicago to San Diego

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Chicago to San Diego. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
 
Picture yourself strolling through the streets of , surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
 
Our flexible Midway Intl. to San Diego Intl. ticket options cater to your travel preferences, with incredible one-way fares from ฿4,190 and roundtrip prices from ฿8,380. Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
 
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at San Diego Intl. and explore and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
 
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your to travel arrangements today and embark on the journey of a lifetime in San Diego.

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 ฿8,380. 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.

Explore a world of travel with Expedia

Chicago Airports

Chicago

O'Hare Intl. to San Diego
฿8,295.00
*Available to Expedia members.