$81 Cheap American Airlines flights San Diego (SAN) to Chicago (ORD)

Make use of the “Price (lowest to highest)” filter on Expedia to look for cheap American Airlines round-trip flights from $161 from SAN to ORD. Affordable one-way fares from $81 are available too.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

January is one of the most affordable months to jet off to Chicago with American Airlines. You could also find excellent prices on return and one-way fares in February.

Start searching one to three months before your departure to get cheap fares on American Airlines flights from San Diego Intl. Airport (SAN) to O’Hare Intl. Airport (ORD). You can save 25% by booking your domestic flight 34 to 86 days in advance compared to last-minute reservations made 6 to 12 days out. You could also reduce costs by buying your fare on a Sunday, as it’s 6% cheaper on average than a Monday, the most expensive day to book.* Get your timing right, and you can enjoy significant savings on domestic journeys.*Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC’s global airline sales database.

American Airlines operates direct flights from San Diego Intl. Airport (SAN) to O’Hare Intl. Airport (ORD), with 14 weekly departures. Simply apply the “Nonstop” and “Airline” filters while searching on Expedia to find all direct American Airlines flights to ORD.

It takes approximately 4h 9m to fly nonstop from San Diego Intl. Airport (SAN) to O’Hare Intl. Airport (ORD) with American Airlines.

If it’s flexibility you’re after, Tuesday offers the most choice for American Airlines flights from San Diego Intl. Airport (SAN) to O’Hare Intl. Airport (ORD). You can pick from 2 different departures.

The earliest flight from SAN to ORD with American Airlines departs at 6:40AM UTC-8. You’ll land at 12:48PM UTC-6. The last American Airlines flight of the day takes off at 1:28PM UTC-8 and arrives at 7:38PM UTC-6. With 20% fewer cancellations for departures before noon, jetting out early is often the smartest choice.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.

American Airlines flights from San Diego Intl. Airport (SAN) to Chicago arrive at O’Hare Intl. Airport (ORD) and Midway Intl. Airport (MDW). The main Chicago hub serviced by this carrier is ORD. It’s worth considering flights landing at nearby airports on Expedia as they may have lower fares.

You’ll likely be on a Boeing 737-800 or an Airbus A321 when flying American Airlines from San Diego Intl. Airport (SAN) to O’Hare Intl. Airport (ORD). However, keep in mind that a different plane may be used due to operational demands.

In most cases, you can reschedule or cancel your flight, although additional charges may apply if your booking was made more than 24 hours ago. Want to keep your options open? Use our “Changes included” or “No cancel fee” filter to find flights that won’t charge you extra if you have to alter your plans. To modify your booking, go to “Trips,” select your flight and click on “Manage Booking” for more information.