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

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

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Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $310
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $310
Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $367
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $367

Frequently asked questions

How much does a flight from San Diego Intl. Airport (SAN) to Dupage Airport (DPA) cost?
Grab a cheap one-way flight or cheap return flight from San Diego Intl. Airport (SAN) to Dupage Airport (DPA) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from San Diego Intl. Airport (SAN) to Dupage Airport (DPA)?
Planning your trip for may help you find better deals, as it's the cheapest month for flights between SAN and DPA. You'll often find the lowest fares during off-peak months.
What is the cheapest airline that flies from San Diego Intl. Airport (SAN) to Dupage Airport (DPA)?
Expedia's filter tool lets you easily compare travel time, airlines and fares all in one place. Customize the search to your preferences, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest SAN to DPA flight.
How many flights per day from San Diego Intl. Airport (SAN) to Dupage Airport (DPA)?
You'll need to catch a flight with a layover if you're traveling from San Diego Intl. Airport (SAN) to Dupage Airport (DPA). Direct flights don't operate daily on this route. However, simply filter your search to include one or two stops to discover the best option for your trip.
What day of the week has the most flights from SAN to DPA?
Friday is typically the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can change based on a range of factors, including the time of year 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 San Diego Intl. Airport (SAN) to Dupage Airport (DPA)?
Opt for a flight from San Diego Intl. Airport (SAN) to Dupage Airport (DPA) that leaves before 3 PM to reduce the risk of cancellations. Departures after this time are on average 22% more likely to be canceled.**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 Chicago from San Diego Intl. Airport (SAN)?
You can land at O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW) when you travel to Chicago on a direct flight from San Diego Intl. Airport (SAN).
Is it cheaper to buy a plane ticket from San Diego Intl. Airport (SAN) to Dupage Airport (DPA) last-minute?
Booking your ticket from SAN to DPA just before your trip is generally more expensive. But if there's some wiggle room with your travel times and dates, you could land a cheap last-minute fare.
Is it cheaper to book a SAN to DPA flight and hotel package?
You'll generally save money by securing a SAN to DPA flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. Once you've chosen your preferred flights and accommodations, you can add extras like tours, activities and car rentals.
Can I cancel or change the date of my flight from San Diego Intl. Airport (SAN) to Dupage Airport (DPA)?
If you booked your SAN to DPA flight within the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for further details.

Travel information

Origin airport
San Diego Intl.
Destination airport
Dupage
Distance
1701 mi

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San Diego to Chicago Flights

The cheapest times to fly from San Diego to Chicago

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 San Diego to Chicago are during the month of . You can find some of the cheapest flights from San Diego to Chicago with Expedia's search tool and vast selection of airlines.

 

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

Sunday is one of the best days to book for cheap flights from San Diego to Chicago: 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 San Diego to Chicago

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 San Diego to Chicago 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 San Diego to Chicago 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 San Diego to Chicago 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.

 

San Diego to Chicago Flights

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