£82 Cheap Flights from Chicago (ORD) to San Diego (SAN)

View £82 flight on Wed, 2 Sept 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at £82 for one-way flights and £168 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Tue, 19 May - Thu, 28 May
ORD
Chicago
SAN
San Diego
£168 Return, found 5 days ago
£168
Return
found 5 days ago
Select Alaska Airlines flight, departing Tue, 19 May from Chicago to San Diego, returning Thu, 28 May, priced at £168 found 5 days ago
Alaska Airlines
Sat, 23 May - Thu, 28 May
ORD
Chicago
SAN
San Diego
£174 Return, found 5 days ago
£174
Return
found 5 days ago
Select Alaska Airlines flight, departing Sat, 23 May from Chicago to San Diego, returning Thu, 28 May, priced at £174 found 5 days ago
Alaska Airlines
Sat, 23 May - Tue, 9 Jun
ORD
Chicago
SAN
San Diego
£176 Return, found 2 days ago
£176
Return
found 2 days ago
Select Alaska Airlines flight, departing Sat, 23 May from Chicago to San Diego, returning Tue, 9 Jun, priced at £176 found 2 days ago
Delta
Tue, 19 May - Tue, 2 Jun
ORD
Chicago
SAN
San Diego
£176 Return, found 5 days ago
£176
Return
found 5 days ago
Select Delta flight, departing Tue, 19 May from Chicago to San Diego, returning Tue, 2 Jun, priced at £176 found 5 days ago
Alaska Airlines
Wed, 20 May - Thu, 28 May
ORD
Chicago
SAN
San Diego
£182 Return, found 5 days ago
£182
Return
found 5 days ago
Select Alaska Airlines flight, departing Wed, 20 May from Chicago to San Diego, returning Thu, 28 May, priced at £182 found 5 days ago
Alaska Airlines
Tue, 2 Jun - Sat, 6 Jun
ORD
Chicago
SAN
San Diego
£183 Return, found 4 days ago
£183
Return
found 4 days ago
Select Alaska Airlines flight, departing Tue, 2 Jun from Chicago to San Diego, returning Sat, 6 Jun, priced at £183 found 4 days ago
Delta
Wed, 27 May - Sat, 6 Jun
ORD
Chicago
SAN
San Diego
£190 Return, found 2 days ago
£190
Return
found 2 days ago
Select Delta flight, departing Wed, 27 May from Chicago to San Diego, returning Sat, 6 Jun, priced at £190 found 2 days ago
American Airlines
Fri, 22 May - Sun, 31 May
ORD
Chicago
SAN
San Diego
£235 Return, found 5 days ago
£235
Return
found 5 days ago
Select American Airlines flight, departing Fri, 22 May from Chicago to San Diego, returning Sun, 31 May, priced at £235 found 5 days ago
United
Fri, 22 May - Sun, 31 May
ORD
Chicago
SAN
San Diego
£319 Return, found 5 days ago
£319
Return
found 5 days ago
Select United flight, departing Fri, 22 May from Chicago to San Diego, returning Sun, 31 May, priced at £319 found 5 days ago
JetBlue Airways
Tue, 21 Jul - Mon, 27 Jul
ORD
Chicago
SAN
San Diego
£342 Return, found 9 hours ago
£342
Return
found 9 hours ago
Select JetBlue Airways flight, departing Tue, 21 Jul from Chicago to San Diego, returning Mon, 27 Jul, priced at £342 found 9 hours ago

Alternative airports near San Diego

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to San Diego Intl. SAN. Cheapest and Closest option available. Average driving time to city centre is 5 minutes. Flights from £283
SAN
San Diego Intl.
CheapestClosest
Average driving time to city centre5 min
Flights from £283

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

May is typically the cheapest month to fly

From £121 - £182 per traveller.

Frequently asked questions

What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.)?
September is typically the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.), with average return fares of approximately £183. This is about 25% lower than the average price throughout the year. September sees lower prices as the summer travel season winds down, and demand for flights often decreases. Other cheap months to fly from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.) include August and October.
Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.)?
Enter ORD to SAN and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.)?
To find a cheap flight from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.)?
The best airline to fly with from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.) will differ from traveller to traveller. If you like to fly early, AA offers early morning flights. If price is the most important factor, WN typically offers the lowest fares. WN offers the most daily flights from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.), which is brilliant if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.)?
Based on booking data from the past year, the cheapest months to fly from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.) are typically September and October, with average return flights around £183. While these months offer great value, the most popular times to travel, which means more flight options, are usually December and November. If you're looking for the best balance, consider that September and October offer the lowest prices, giving you more flexibility with your budget.
How many flights per day from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.)?
There are approximately 13 nonstop flights per day from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.). For even more choice, look at flights that include layovers, as you'll find around 162 connecting flights per day. Some common connection points include McCarran Intl. (LAS), Denver Intl. (DEN), and Dallas-Fort Worth Intl. (DFW).
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.)?
The earliest flight from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.) typically departs at approximately 12:00 AM local time, operated by American Airlines. This is a seasonal service active in December. An early departure like this can help you maximise your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.)?
You'll typically find the most flights from Chicago O'Hare International Airport (ORD) to San Diego International Airport (SAN) on a Thursday, with around 94 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include United Airlines, American Airlines, and Delta Air Lines. Thursday offers notably more flight options compared to other days of the week.
What are the most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.)?
The most popular departure times for flights from Chicago O'Hare International Airport (ORD) to San Diego International Airport (SAN) are in the early morning, from 6am to 9am. About 31% of passengers prefer this time window. Many major carriers, including United Airlines, Delta Air Lines and Alaska Airlines, offer flights during this window. This timing works well because it allows you to get an early start on your travel day and arrive in San Diego with plenty of time to enjoy your destination.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.)?
Direct flights from ORD to SAN usually take about 4 hours 30 minutes, traveling roughly 1,721 miles. If you opt for a connecting flight, expect to add around 3 hours 30 minutes to your journey. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.)?
Select the "Business class" and "First class" filters when looking for ORD to SAN flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for San Diego from O'Hare Intl. (ORD)?
If you're planning to travel to San Diego from O'Hare Intl. (ORD), you can fly directly into San Diego Intl. (SAN) Some flights may connect through major hubs like Love Field (DAL), Denver Intl. (DEN), McCarran Intl. (LAS) before reaching San Diego. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.) flight and hotel package?
Securing a Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.)?
If you booked your Chicago, IL (ORD-O'Hare Intl.) to San Diego, CA (SAN-San Diego Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
San Diego Intl.
Airlines serving
Alaska Airlines, JetBlue Airways
Return price
£168
Distance
2752 km
Average flight time
2 hours 36 mins

Book with confidence

Compare flights from Chicago to San Diego easily and book with confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Chicago to San Diego. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to San Diego Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from O'Hare Intl. to San Diego Intl..  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from O'Hare Intl. (ORD) to San Diego Intl. (SAN)

The easiest way to view the best deals on flights from Chicago to San Diego today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from O'Hare Intl. to San Diego Intl. start at just £168 and range up to £342.  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near Chicago and San Diego
  • booking your flight during May, the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your Chicago to San Diego flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from O'Hare Intl. to San Diego Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

Compare flights from Chicago to San Diego easily and book with confidence

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*Available to Expedia members.