A large bridge spanning a body of water with a city skyline in the background.

RM527 Cheap Flights from Chicago (MDW) to San Diego (SAN)

View RM527 flight on Sat, 12 Sept 2026Opens in a new window

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

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our rewards
    Sign in

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

Prices were available within the past 7 days and start at RM527 for one-way flights and RM1,135 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
SAN
San Diego
RM1,135 Return, found 4 days ago
RM1,135
Return
found 4 days ago
Select Delta flight, departing Wed, 9 Sept from Chicago to San Diego, returning Wed, 16 Sept, priced at RM1,135 found 4 days ago
Delta
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
SAN
San Diego
RM1,136 Return, found 4 days ago
RM1,136
Return
found 4 days ago
Select Delta flight, departing Wed, 9 Sept from Chicago to San Diego, returning Wed, 16 Sept, priced at RM1,136 found 4 days ago
Delta
Sat, 12 Sept - Sat, 19 Sept
MDW
Chicago
SAN
San Diego
RM1,262 Return, found 2 days ago
RM1,262
Return
found 2 days ago
Select Delta flight, departing Sat, 12 Sept from Chicago to San Diego, returning Sat, 19 Sept, priced at RM1,262 found 2 days ago
Delta
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
SAN
San Diego
RM1,341 Return, found 4 days ago
RM1,341
Return
found 4 days ago
Select Delta flight, departing Wed, 9 Sept from Chicago to San Diego, returning Wed, 16 Sept, priced at RM1,341 found 4 days ago
Delta
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
SAN
San Diego
RM1,484 Return, found 4 days ago
RM1,484
Return
found 4 days ago
Select Delta flight, departing Wed, 9 Sept from Chicago to San Diego, returning Wed, 16 Sept, priced at RM1,484 found 4 days ago
Delta
Mon, 7 Sept - Mon, 14 Sept
MDW
Chicago
SAN
San Diego
RM1,733 Return, found 6 days ago
RM1,733
Return
found 6 days ago
Select Delta flight, departing Mon, 7 Sept from Chicago to San Diego, returning Mon, 14 Sept, priced at RM1,733 found 6 days ago
Delta
Mon, 7 Sept - Mon, 14 Sept
MDW
Chicago
SAN
San Diego
RM1,937 Return, found 6 days ago
RM1,937
Return
found 6 days ago
Select Delta flight, departing Mon, 7 Sept from Chicago to San Diego, returning Mon, 14 Sept, priced at RM1,937 found 6 days ago
Delta
Mon, 7 Sept - Mon, 14 Sept
MDW
Chicago
SAN
San Diego
RM1,938 Return, found 6 days ago
RM1,938
Return
found 6 days ago
Select Delta flight, departing Mon, 7 Sept from Chicago to San Diego, returning Mon, 14 Sept, priced at RM1,938 found 6 days ago
Delta
Mon, 7 Sept - Mon, 14 Sept
MDW
Chicago
SAN
San Diego
RM2,081 Return, found 6 days ago
RM2,081
Return
found 6 days ago
Select Delta flight, departing Mon, 7 Sept from Chicago to San Diego, returning Mon, 14 Sept, priced at RM2,081 found 6 days ago
Delta
Mon, 7 Sept - Mon, 14 Sept
MDW
Chicago
SAN
San Diego
RM2,141 Return, found 6 days ago
RM2,141
Return
found 6 days ago
Select Delta flight, departing Mon, 7 Sept from Chicago to San Diego, returning Mon, 14 Sept, priced at RM2,141 found 6 days ago

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

February is typically the cheapest month to fly

From RM 457 - RM 1,023 per traveller.

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 RM1,135. 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.

Travel information

Origin airport
Midway Intl.
Destination airport
San Diego Intl.
Return price
RM1,135
Distance
2761 km
Average flight time
2 hours 8 mins

Book with confidence

Perfect flights from Chicago to San Diego

Your Journey from Chicago to San Diego

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to San Diego caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta. Our selection of flights from Midway Intl. to San Diego Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Chicago to San Diego Flights

Experience the joy of finding cheap flights from Midway Intl. to San Diego Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from RM527 and roundtrip prices from RM1,135*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to San Diego with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant San Diego

Picture yourself stepping off the plane in San Diego and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Chicago to San Diego Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Chicago to San Diego.
 

Beyond the Flight – Exploring San Diego

With Expedia, your adventure extends beyond the flight. Explore San Diego at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Chicago to San Diego with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Chicago to San Diego with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.
Perfect flights from Chicago to San Diego

Explore a world of travel with Expedia

*Available to Expedia members.