S$158 Cheap Flights from Chicago to San Diego

View S$158 flight on Tue, 16 Dec, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to San Diego Intl. Airport (SAN)

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

Prices were available within the past 7 days and start at S$158 for one-way flights and S$323 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Tue, 16 Dec - Wed, 7 Jan
ORD
Chicago
SAN
San Diego
S$323 Return, found 23 hours ago
S$323
Return
found 23 hours ago
Select American Airlines flight, departing Tue, 16 Dec from Chicago to San Diego, returning Wed, 7 Jan, priced at S$323 found 23 hours ago
American Airlines
Tue, 16 Dec - Wed, 7 Jan
ORD
Chicago
SAN
San Diego
S$329 Return, found 23 hours ago
S$329
Return
found 23 hours ago
Select American Airlines flight, departing Tue, 16 Dec from Chicago to San Diego, returning Wed, 7 Jan, priced at S$329 found 23 hours ago
American Airlines
Tue, 16 Dec - Wed, 7 Jan
ORD
Chicago
SAN
San Diego
S$330 Return, found 23 hours ago
S$330
Return
found 23 hours ago
Select American Airlines flight, departing Tue, 16 Dec from Chicago to San Diego, returning Wed, 7 Jan, priced at S$330 found 23 hours ago
Delta
Tue, 16 Dec - Wed, 7 Jan
ORD
Chicago
SAN
San Diego
S$332 Return, found 23 hours ago
S$332
Return
found 23 hours ago
Select Delta flight, departing Tue, 16 Dec from Chicago to San Diego, returning Wed, 7 Jan, priced at S$332 found 23 hours ago
United
Tue, 16 Dec - Wed, 7 Jan
ORD
Chicago
SAN
San Diego
S$339 Return, found 23 hours ago
S$339
Return
found 23 hours ago
Select United flight, departing Tue, 16 Dec from Chicago to San Diego, returning Wed, 7 Jan, priced at S$339 found 23 hours ago
United
Mon, 17 Nov - Mon, 24 Nov
ORD
Chicago
SAN
San Diego
S$342 Return, found 4 days ago
S$342
Return
found 4 days ago
Select United flight, departing Mon, 17 Nov from Chicago to San Diego, returning Mon, 24 Nov, priced at S$342 found 4 days ago
American Airlines
Mon, 17 Nov - Mon, 24 Nov
ORD
Chicago
SAN
San Diego
S$343 Return, found 4 days ago
S$343
Return
found 4 days ago
Select American Airlines flight, departing Mon, 17 Nov from Chicago to San Diego, returning Mon, 24 Nov, priced at S$343 found 4 days ago
United
Tue, 16 Dec - Wed, 7 Jan
ORD
Chicago
SAN
San Diego
S$345 Return, found 23 hours ago
S$345
Return
found 23 hours ago
Select United flight, departing Tue, 16 Dec from Chicago to San Diego, returning Wed, 7 Jan, priced at S$345 found 23 hours ago
United
Thu, 18 Dec - Wed, 7 Jan
ORD
Chicago
SAN
San Diego
S$351 Return, found 23 hours ago
S$351
Return
found 23 hours ago
Select United flight, departing Thu, 18 Dec from Chicago to San Diego, returning Wed, 7 Jan, priced at S$351 found 23 hours ago
Delta
Tue, 16 Dec - Wed, 7 Jan
ORD
Chicago
SAN
San Diego
S$353 Return, found 23 hours ago
S$353
Return
found 23 hours ago
Select Delta flight, departing Tue, 16 Dec from Chicago to San Diego, returning Wed, 7 Jan, priced at S$353 found 23 hours ago

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

February is typically the cheapest month to fly

From S$129 - S$416 per traveller.
Chicago to San Diego route information
Origin airport
O'Hare Intl.
Destination airport
San Diego Intl.
Airlines serving
American Airlines, Delta, United
Return price
S$323
Distance
2752 km
Average flight time
2 hours 27 mins

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 American Airlines, Delta, United. Our selection of flights from O'Hare 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 O'Hare 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 S$158 and roundtrip prices from S$323*.
 

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.

Frequently asked questions

How much is a flight from O'Hare Airport to San Diego Intl. Airport (SAN)?
The lowest price advertised for a round-trip journey between O'Hare Intl. Airport (ORD) and San Diego Airport is S$323. But you better act fast. This price is based on fares listed within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from ORD to SAN?
This can differ between airlines, as each has its own set of terms and conditions. Visit the Customer Service Portal, where there are simple instructions on how to cancel your flight online.
How do I find cheap flights from ORD 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 ORD to San Diego Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from O'Hare Airport to San Diego Intl. Airport (SAN)?
The flying distance between O'Hare Airport and SAN is 2,800 kilometres. Close your eyes or get stuck into a book and the journey will whiz by.
Which airlines fly direct from ORD to SAN?
With 121 monthly flights operating from ORD to San Diego Intl. Airport (SAN), United Airlines (UA) is a top choice. If you'd like more options, check out the ticket prices from American Airlines (AA). This airlines operates 91 monthly flights between these airports.
Are ORD to SAN flight tickets cheaper when they're purchased at the last minute?
Late planners can sometimes nab a bargain, with some of the cheapest airfares from O'Hare Airport to San Diego Intl. Airport (SAN) appearing a few weeks before the date of departure. If you'd rather book ahead of time, Expedia compares and updates all the best flight deals frequently — as early as a year in advance in some cases. It depends on the carrier though, as not all airlines publish prices that far in advance.

Explore a world of travel with Expedia

San Diego Airports

Carlsbad

Chicago to McClellan-Palomar
S$325.90
Chicago Airports

Chicago

Midway Intl. to San Diego
S$428.00
*Available to Expedia members.