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

Popular airlines from Chicago, IL (PWK-Chicago Executive) to San Diego Intl. Airport (SAN)

Frequently asked questions

How much does a flight from Chicago Executive Airport (PWK) to San Diego Intl. Airport (SAN) cost?
Snag a cheap one-way flight or cheap return flight from Chicago Executive Airport (PWK) to San Diego Intl. Airport (SAN) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Chicago Executive Airport (PWK) to San Diego Intl. Airport (SAN)?
is the cheapest month to fly from PWK to SAN. Traveling during quieter months is often the key to scoring lower fares.
Which airlines fly direct from Chicago Executive Airport (PWK) to San Diego Intl. Airport (SAN)?
There's no direct route from Chicago, IL (PWK-Chicago Executive) to San Diego Intl. Airport (SAN). However, you'll find other airports offering nonstop flights. Begin your journey at O'Hare Intl. Airport (ORD) and fly straight to San Diego without a layover.
What is the cheapest airline that flies from Chicago Executive Airport (PWK) to San Diego Intl. Airport (SAN)?
Use the filters on Expedia to compare different airlines and find the cheapest carrier that'll fly you from PWK to SAN. Then, sort your results by "Price (lowest to highest)" to score a good deal.
How many flights per day from Chicago Executive Airport (PWK) to San Diego Intl. Airport (SAN)?
There aren't any daily direct flights available from Chicago Executive Airport (PWK) to San Diego Intl. Airport (SAN). But you can book flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be on your way before you know it.
What day of the week has the most flights from PWK to SAN?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can change depending on a range of factors, including the season and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Chicago Executive Airport (PWK) to San Diego Intl. Airport (SAN)?
Choose a flight from Chicago Executive Airport (PWK) to San Diego Intl. Airport (SAN) that takes off before 3 PM to reduce the likelihood of delays and cancellations. Later departures have a 22% higher chance of being canceled, on average.**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.
Is it cheaper to buy a plane ticket from Chicago Executive Airport (PWK) to San Diego Intl. Airport (SAN) last-minute?
Booking your plane ticket from PWK to SAN shortly before your journey is typically more expensive. However, if there's some wiggle room with your departure dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a PWK to SAN flight and hotel package?
Booking a PWK to SAN flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Choose from our wide range of hotels and then add flights, car rentals and activities 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 Executive Airport (PWK) to San Diego Intl. Airport (SAN)?
You can usually reschedule or cancel your PWK to SAN flight. However, for bookings made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Origin airport
Chicago Executive
Destination airport
San Diego Intl.
Distance
1722 mi

Book with confidence

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 . 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 2026. You can also book with separate airlines for your outbound and return journeys, from 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.

 

Chicago to San Diego Flights

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*Available to One Key members.