S$148 Cheap Flights from San Diego to Chicago

View S$148 flight on Sat, 18 Oct, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at S$148 for one-way flights and S$313 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Sat, 20 Sep - Mon, 22 Sep
SAN
San Diego
ORD
Chicago
S$313 Return, found 6 days ago
S$313
Return
found 6 days ago
Select United flight, departing Sat, 20 Sep from San Diego to Chicago, returning Mon, 22 Sep, priced at S$313 found 6 days ago
Delta
Sat, 20 Sep - Mon, 22 Sep
SAN
San Diego
ORD
Chicago
S$330 Return, found 6 days ago
S$330
Return
found 6 days ago
Select Delta flight, departing Sat, 20 Sep from San Diego to Chicago, returning Mon, 22 Sep, priced at S$330 found 6 days ago
American Airlines
Sat, 20 Sep - Mon, 22 Sep
SAN
San Diego
ORD
Chicago
S$332 Return, found 6 days ago
S$332
Return
found 6 days ago
Select American Airlines flight, departing Sat, 20 Sep from San Diego to Chicago, returning Mon, 22 Sep, priced at S$332 found 6 days ago
United
Sat, 20 Sep - Mon, 22 Sep
SAN
San Diego
ORD
Chicago
S$332 Return, found 6 days ago
S$332
Return
found 6 days ago
Select United flight, departing Sat, 20 Sep from San Diego to Chicago, returning Mon, 22 Sep, priced at S$332 found 6 days ago
United
Sat, 20 Sep - Mon, 22 Sep
SAN
San Diego
ORD
Chicago
S$345 Return, found 6 days ago
S$345
Return
found 6 days ago
Select United flight, departing Sat, 20 Sep from San Diego to Chicago, returning Mon, 22 Sep, priced at S$345 found 6 days ago
Delta
Sat, 20 Sep - Mon, 22 Sep
SAN
San Diego
ORD
Chicago
S$349 Return, found 6 days ago
S$349
Return
found 6 days ago
Select Delta flight, departing Sat, 20 Sep from San Diego to Chicago, returning Mon, 22 Sep, priced at S$349 found 6 days ago
United
Sat, 20 Sep - Mon, 22 Sep
SAN
San Diego
ORD
Chicago
S$358 Return, found 6 days ago
S$358
Return
found 6 days ago
Select United flight, departing Sat, 20 Sep from San Diego to Chicago, returning Mon, 22 Sep, priced at S$358 found 6 days ago
United
Sat, 20 Sep - Mon, 22 Sep
SAN
San Diego
ORD
Chicago
S$362 Return, found 6 days ago
S$362
Return
found 6 days ago
Select United flight, departing Sat, 20 Sep from San Diego to Chicago, returning Mon, 22 Sep, priced at S$362 found 6 days ago
Delta
Wed, 10 Sep - Sun, 14 Sep
SAN
San Diego
ORD
Chicago
S$364 Return, found 3 days ago
S$364
Return
found 3 days ago
Select Delta flight, departing Wed, 10 Sep from San Diego to Chicago, returning Sun, 14 Sep, priced at S$364 found 3 days ago
Delta
Sat, 20 Sep - Mon, 22 Sep
SAN
San Diego
ORD
Chicago
S$368 Return, found 6 days ago
S$368
Return
found 6 days ago
Select Delta flight, departing Sat, 20 Sep from San Diego to Chicago, returning Mon, 22 Sep, priced at S$368 found 6 days ago

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

September is typically the cheapest month to fly

From S$118 - S$229 per traveller.

Graph displaying average flight prices per month

San Diego to Chicago route information
Origin airport
San Diego Intl.
Destination airport
O'Hare Intl.
Return price
S$312
Distance
2752 km
Average flight time
6 hours 15 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 American Airlines, United, Delta. Our selection of flights from San Diego Intl. to O'Hare 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 San Diego to Chicago Flights

Experience the joy of finding cheap flights from San Diego Intl. to O'Hare Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$148 and roundtrip prices from S$313*.
 

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 Intl. Airport (SAN) to O'Hare Intl. Airport (ORD)?
If you're planning on travelling between SAN and ORD, round-trip journeys start from S$313. This figure is based on fares quoted within the last 7 days on Expedia for flights departing within the next year, so don't let a good deal slip through your fingers. Book today 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 SAN to ORD?
The majority of flights can be cancelled online, but whether you are charged a fee differs between airlines. If you do have to cancel your trip, follow the easy instructions in the Customer Service Portal.
How do I find cheap flights from San Diego Airport to O'Hare Intl. Airport (ORD) 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 Intl. Airport (SAN) to O'Hare Intl. Airport (ORD) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from San Diego Intl. Airport (SAN) to ORD?
The flying distance between SAN and O'Hare Airport is 2,800 kilometres. Squeeze in a nap or make a start on the latest bestseller and the journey will zip by.
Which airlines fly direct from San Diego Airport to O'Hare Intl. Airport (ORD)?
A leading airline that flies from San Diego Intl. Airport (SAN) to O'Hare Intl. Airport (ORD) is United Airlines (UA). It offers 121 flights monthly. If you'd like more options, check out the ticket prices from American Airlines (AA). This airlines operates 91 flights a month between these airports.
Are San Diego Intl. Airport (SAN) to O'Hare Airport flight tickets cheaper when they're purchased at the last minute?
It is possible to pick up amazing last-minute deals from San Diego Intl. Airport (SAN) to O'Hare Airport, but it can also be hit-or-miss. As many airlines publish prices up to a year in advance, it's worthwhile keeping an eye on fares early and being ready to book when you spot a bargain. Expedia compares air carrier prices and updates flight deals often, so you can rest assured you're always getting the latest offers.

Explore a world of travel with Expedia

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