$64 Cheap Flights from Chicago (ORD) to San Diego (SAN)

View $64 flight on Tue, Aug 5, 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 $64 for one-way flights and $111 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Aug 5 - Tue, Aug 12
ORD
Chicago
SAN
San Diego
$111 Roundtrip, found 12 hours ago
$111
Roundtrip
found 12 hours ago
Select Spirit Airlines flight, departing Tue, Aug 5 from Chicago to San Diego, returning Tue, Aug 12, priced at $111 found 12 hours ago
Spirit Airlines
Tue, Aug 5 - Wed, Aug 6
ORD
Chicago
SAN
San Diego
$114 Roundtrip, found 6 hours ago
$114
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Tue, Aug 5 from Chicago to San Diego, returning Wed, Aug 6, priced at $114 found 6 hours ago
Spirit Airlines
Tue, Aug 5 - Thu, Aug 14
ORD
Chicago
SAN
San Diego
$117 Roundtrip, found 12 hours ago
$117
Roundtrip
found 12 hours ago
Select Spirit Airlines flight, departing Tue, Aug 5 from Chicago to San Diego, returning Thu, Aug 14, priced at $117 found 12 hours ago
Southwest Airlines
Sat, Sep 6 - Wed, Sep 10
ORD
Chicago
SAN
San Diego
$124 Roundtrip, found 8 hours ago
$124
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Sat, Sep 6 from Chicago to San Diego, returning Wed, Sep 10, priced at $124 found 8 hours ago
Spirit Airlines
Tue, Aug 5 - Fri, Aug 15
ORD
Chicago
SAN
San Diego
$128 Roundtrip, found 11 hours ago
$128
Roundtrip
found 11 hours ago
Select Spirit Airlines flight, departing Tue, Aug 5 from Chicago to San Diego, returning Fri, Aug 15, priced at $128 found 11 hours ago
Spirit Airlines
Thu, Aug 7 - Tue, Aug 12
ORD
Chicago
SAN
San Diego
$129 Roundtrip, just found
$129
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Aug 7 from Chicago to San Diego, returning Tue, Aug 12, priced at $129 just found
Southwest Airlines
Tue, Aug 26 - Wed, Sep 3
ORD
Chicago
SAN
San Diego
$134 Roundtrip, found 15 hours ago
$134
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Tue, Aug 26 from Chicago to San Diego, returning Wed, Sep 3, priced at $134 found 15 hours ago
Hawaiian Airlines
Sat, Oct 4 - Tue, Oct 14
ORD
Chicago
SAN
San Diego
$143 Roundtrip, found 11 hours ago
$143
Roundtrip
found 11 hours ago
Select Hawaiian Airlines flight, departing Sat, Oct 4 from Chicago to San Diego, returning Tue, Oct 14, priced at $143 found 11 hours ago
American Airlines
Wed, Aug 20 - Sat, Aug 23
ORD
Chicago
CLD
Carlsbad
$163 Roundtrip, found 11 hours ago
$163
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, Aug 20 from Chicago to Carlsbad, returning Sat, Aug 23, priced at $163 found 11 hours ago
United
Wed, Aug 13 - Sat, Aug 16
ORD
Chicago
SAN
San Diego
$171 Roundtrip, just found
$171
Roundtrip
just found
Select United flight, departing Wed, Aug 13 from Chicago to San Diego, returning Sat, Aug 16, priced at $171 just found

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

September is typically the cheapest month to fly

From $83 - $157 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (ORD) to San Diego (SAN)
Origin airport
O'Hare Intl.
Destination airport
San Diego Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Frontier Airlines, Hawaiian Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United
Roundtrip price
$111
Distance
1720 mi
Average flight time
2 hours 20 mins

Chicago to San Diego Flights

The cheapest times to fly from Chicago to San Diego

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to San Diego are during the month of August. You can find some of the cheapest flights from Chicago to San Diego with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to San Diego

Sunday is one of the best days to book for cheap flights from Chicago to San Diego: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to San Diego

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to San Diego in 2025. You can also book with separate airlines for your outbound and return journeys, from $64 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to San Diego flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to San Diego airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to San Diego Intl. Airport (SAN) cost?
Book cheap return tickets starting at $139 from O'Hare Intl. Airport (ORD) to San Diego Intl. Airport (SAN). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a American Airlines and Southwest Airlines flight leaving ORD on August 5 2025 and touching down at SAN. The price was last updated on July 9 2025 and has not changed since.
What is the cheapest month to fly from ORD to SAN?
The cheapest flights from ORD to SAN are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to San Diego Intl. Airport (SAN)?
Take a direct flight with United Airlines and travel straight from O'Hare Intl. Airport (ORD) to San Diego Intl. Airport (SAN).
What is the cheapest airline that flies from ORD to SAN?
Travel from ORD to SAN with Alaska Airlines. This carrier currently has the cheapest one-way fare on this route, starting from $86. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on October 4 2025. Prices were last updated on July 9 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to San Diego Intl. Airport (SAN)?
When jetting out of O'Hare Intl. Airport (ORD), you can take your pick from an average of 5 daily nonstop flights to San Diego Intl. Airport (SAN).
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to San Diego Intl. Airport (SAN)?
Flights between ORD and SAN are their busiest at 1 PM. If you're after a more relaxed trip and possibly cheaper tickets, look for a time outside the usual busy windows.
What day of the week has the most flights from ORD to SAN?
If you travel on a Sunday, you'll get the biggest range of options for flights from O'Hare Intl. Airport (ORD) to San Diego Intl. Airport (SAN).
What is the earliest flight from O'Hare Intl. Airport (ORD) to San Diego Intl. Airport (SAN)?
O'Hare Intl. Airport (ORD)'s earliest flight to San Diego Intl. Airport (SAN) leaves at approximately 8:50AM UTC-6. With a total flight time of 4h 38m, you'll arrive at around 11:28AM UTC-8.
How long does it take to fly from O'Hare Intl. Airport (ORD) to San Diego Intl. Airport (SAN)?
Flights from ORD to SAN have an average travel time of 4 hours and 33 minutes. The distance between the two airports is 1,700 mi.
What airline has the least delays from ORD to SAN?
United Airlines has the best performance for on-time direct flights from O'Hare Intl. Airport (ORD) to San Diego Intl. Airport (SAN), with an on-time rating of 80%. Use the Expedia App to view your flight schedule before you leave and get real-time updates about any changes.
What is the best time to fly from O'Hare Intl. Airport (ORD) to San Diego Intl. Airport (SAN)?
To arrive at San Diego Intl. Airport (SAN) on time, pick a flight that leaves O'Hare Intl. Airport (ORD) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for San Diego from O'Hare Intl. Airport (ORD)?
San Diego Intl. Airport (SAN) is the only airport in San Diego with direct flights from O'Hare Intl. Airport (ORD). Compare your options and find cheap fares on Expedia.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to San Diego Intl. Airport (SAN) last-minute?
Holding off until right before your break to book your flight from ORD to SAN generally means paying more. Although you may find some last-minute deals, they're not always guaranteed. Allow some flexibility in your schedule for the best chance of getting a bargain.
Is it cheaper to book an ORD to SAN flight and hotel package?
Securing an ORD to SAN flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Choose from our extensive range of stays and then add activities, car rentals and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to San Diego Intl. Airport (SAN)?
Usually, it's possible to reschedule or cancel your ORD to SAN flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find more information on our Customer Service portal.

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