S$539 Cheap Flights from San Diego to Chicago

View S$539 flight on Thu, 8 Oct, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at S$539 for one-way flights and S$1,026 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, 8 Oct - Sun, 11 Oct
SAN
San Diego
MDW
Chicago
S$1,026 Return, found 11 hours ago
S$1,026
Return
found 11 hours ago
Select Delta flight, departing Thu, 8 Oct from San Diego to Chicago, returning Sun, 11 Oct, priced at S$1,026 found 11 hours ago
Delta
Thu, 8 Oct - Sun, 11 Oct
SAN
San Diego
MDW
Chicago
S$1,142 Return, found 11 hours ago
S$1,142
Return
found 11 hours ago
Select Delta flight, departing Thu, 8 Oct from San Diego to Chicago, returning Sun, 11 Oct, priced at S$1,142 found 11 hours ago

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

January is typically the cheapest month to fly

From S$153 - S$834 per traveller.
San Diego to Chicago route information
Origin airport
San Diego Intl.
Destination airport
Midway Intl.
Return price
S$1,026
Distance
2761 km
Average flight time
5 hours 55 mins

Perfect flights from San Diego to Chicago

Your Journey from San Diego to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from San Diego to Chicago 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 San Diego Intl. to Midway Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 6 airlines, you're bound to find the perfect flight.
 

Maximizing Value with San Diego to Chicago Flights

Experience the joy of finding cheap flights from San Diego Intl. to Midway Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$539 and roundtrip prices from S$1,026*.
 

Pre-Flight Essentials

Ensure a smooth journey from San Diego to Chicago 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 Chicago

Picture yourself stepping off the plane in Chicago 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 San Diego to Chicago 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 San Diego to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago 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 San Diego to Chicago 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 San Diego to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from San Diego Airport to MDW?
Based on fares quoted within the last 7 days on Expedia for flights departing within the next year, round-trip journeys from SAN to MDW start from S$1,026. Book today to score the best price for your exciting adventure. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from SAN to MDW?
Each air carrier has its own set of terms and conditions. If you do decide to cancel, follow the easy instructions on our Customer Service Portal.
How do I find cheap flights from San Diego Airport to Midway Airport 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 San Diego Airport to Midway Intl. Airport (MDW) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from San Diego Airport to Midway Airport?
You'll be up above the clouds for a while, as the flight distance from San Diego to Chicago is 2,800 kilometres. Create a playlist of your favourite podcasts before leaving home to keep yourself entertained during the journey.
Which airlines fly direct from San Diego Airport to Midway Airport?
Operating 78 monthly flights, Southwest Airlines (WN) is a great choice when flying directly from SAN to Chicago Airport.
Are San Diego Intl. Airport (SAN) to Midway Airport flight tickets cheaper when they're purchased at the last minute?
Booking last minute from SAN to Chicago Airport can be hit-or-miss. You may be able to find a bargain, but then again, you could miss out! If you'd prefer to start planning ahead of time, Expedia compares flight deals up to a year in advance. Just remember that not all airlines list their prices that far in advance. Our top tip? Check back often as prices are updated regularly.

Explore a world of travel with Expedia

*Available to Expedia members.