S$175 Cheap Flights from San Diego to Chicago

View S$175 flight on Sun, 21 Dec, 2025Opens in a new window

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

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save up to 40% on select hotels after you book a flight*
  • trophy illustration

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

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

Prices were available within the past 7 days and start at S$175 for one-way flights and S$420 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Sun, 21 Dec - Sat, 3 Jan
SAN
San Diego
ORD
Chicago
S$420 Return, found 6 days ago
S$420
Return
found 6 days ago
Select United flight, departing Sun, 21 Dec from San Diego to Chicago, returning Sat, 3 Jan, priced at S$420 found 6 days ago
United
Sun, 21 Dec - Sat, 3 Jan
SAN
San Diego
ORD
Chicago
S$447 Return, found 6 days ago
S$447
Return
found 6 days ago
Select United flight, departing Sun, 21 Dec from San Diego to Chicago, returning Sat, 3 Jan, priced at S$447 found 6 days ago
United
Sun, 21 Dec - Sat, 3 Jan
SAN
San Diego
ORD
Chicago
S$460 Return, found 6 days ago
S$460
Return
found 6 days ago
Select United flight, departing Sun, 21 Dec from San Diego to Chicago, returning Sat, 3 Jan, priced at S$460 found 6 days ago
United
Sun, 21 Dec - Sat, 3 Jan
SAN
San Diego
ORD
Chicago
S$463 Return, found 6 days ago
S$463
Return
found 6 days ago
Select United flight, departing Sun, 21 Dec from San Diego to Chicago, returning Sat, 3 Jan, priced at S$463 found 6 days ago
United
Sun, 21 Dec - Sat, 3 Jan
SAN
San Diego
ORD
Chicago
S$466 Return, found 6 days ago
S$466
Return
found 6 days ago
Select United flight, departing Sun, 21 Dec from San Diego to Chicago, returning Sat, 3 Jan, priced at S$466 found 6 days ago
American Airlines
Sun, 21 Dec - Sat, 3 Jan
SAN
San Diego
ORD
Chicago
S$479 Return, found 6 days ago
S$479
Return
found 6 days ago
Select American Airlines flight, departing Sun, 21 Dec from San Diego to Chicago, returning Sat, 3 Jan, priced at S$479 found 6 days ago
United
Sun, 21 Dec - Sat, 3 Jan
SAN
San Diego
ORD
Chicago
S$486 Return, found 6 days ago
S$486
Return
found 6 days ago
Select United flight, departing Sun, 21 Dec from San Diego to Chicago, returning Sat, 3 Jan, priced at S$486 found 6 days ago
United
Sun, 21 Dec - Sat, 3 Jan
SAN
San Diego
ORD
Chicago
S$492 Return, found 6 days ago
S$492
Return
found 6 days ago
Select United flight, departing Sun, 21 Dec from San Diego to Chicago, returning Sat, 3 Jan, priced at S$492 found 6 days ago
United
Sun, 21 Dec - Sat, 3 Jan
SAN
San Diego
ORD
Chicago
S$499 Return, found 6 days ago
S$499
Return
found 6 days ago
Select United flight, departing Sun, 21 Dec from San Diego to Chicago, returning Sat, 3 Jan, priced at S$499 found 6 days ago
Delta
Thu, 4 Dec - Tue, 9 Dec
SAN
San Diego
ORD
Chicago
S$533 Return, found 3 hours ago
S$533
Return
found 3 hours ago
Select Delta flight, departing Thu, 4 Dec from San Diego to Chicago, returning Tue, 9 Dec, priced at S$533 found 3 hours ago

Black Friday Sale

Save up to 50% on select hotels
Book now

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

September is typically the cheapest month to fly

From S$127 - S$492 per traveller.
San Diego to Chicago route information
Origin airport
San Diego Intl.
Destination airport
O'Hare Intl.
Return price
S$420
Distance
2752 km
Average flight time
6 hours 9 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 United, American Airlines, 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$175 and roundtrip prices from S$420*.
 

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$420. 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

Chicago Airports

Chicago

San Diego to Midway Intl.
S$532.20
San Diego Airports

Carlsbad

*Available to Expedia members.