Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

Cheap flights from Chicago (CHI) to San Diego (SAN)

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Lowest round trip fares by airline from Chicago and San Diego

Cheapest prices ($70 One Way, $87 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in San Diego

Pleasant Inn

Pleasant Inn

2.5 out of 5
5550 Clairemont Mesa Blvd, San Diego, CA
The price is $135 per night from Aug 8 to Aug 8
Located in Clairemont, this motel is within 6 mi (10 km) of Westfield UTC, Mission Bay Park, and Fashion Valley Mall. Hotel Circle and Balboa Park are also within ...
4.1/5Very Good! (7 reviews)
"It was nice and clean the staff were very nice I would come back."

Reviewed on Aug 31, 2020

Pleasant Inn
E-Z 8 Motel Old Town

E-Z 8 Motel Old Town

2.5 out of 5
4747 Pacific Highway, San Diego, CA
The price is $89 per night from Sep 2 to Sep 2
Located in Old Town San Diego, this motel is within 1 mi (2 km) of Old Town Trolley Tours, Old Town San Diego State Park, and Hotel Circle. Mission Bay and University ...
2.4/5 (7 reviews)
"Calm &relaxed"

Reviewed on Apr 23, 2021

E-Z 8 Motel Old Town
Kings Inn San Diego - Seaworld - Zoo

Kings Inn San Diego - Seaworld - Zoo

2.5 out of 5
1333 Hotel Cir S, San Diego, CA
The price is $108 per night from Aug 19 to Aug 19
Located in Mission Valley, this hotel is within 2 mi (3 km) of Riverwalk Golf Club, Fashion Valley Mall, and Old Town San Diego State Park. University of San ...
4.2/5Very Good! (11 reviews)
"We had a nice stay, the staff was very friendly. The only thing was it was a little noisy in the mornings when people would walk outside to check out and the walls are a little thin. Everything else was great!"

Reviewed on Oct 13, 2020

Kings Inn San Diego - Seaworld - Zoo
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Flights Review

Fly From Chicago to San Diego

Origin Chicago
Destination San Diego
Number of Daily Flights 36
Earliest Flight Departure Date Aug 10
Latest Flight Departure Date Aug 11
Popular Airlines Alaska Airlines

Cheap flights from Chicago to San Diego

When you're headed to San Diego from Chicago, get ready to enjoy warmth and sunshine as soon as you land. You may even want to choose a rental car that has a convertible top, so that you can make the most of your ground travel during your stay. In addition to beautiful weather year-round, San Diego offers both business and leisure guests many fun excursion opportunities such as Lego Land and the San Diego Zoo.

You can drive from the airport to the San Diego Bay and watch the cargo ships dock, or explore the many urban canyons, scattered between neighborhoods like Mission Beach and Ocean Beach. A rental car is a definite must for getting around this sprawling urban environment.

Key Facts

While in San Diego, you can take the short drive to the Mexican border. You may also want to visit the Cleveland National Forest, located just half an hour from downtown. Since San Diego is spread over such a large area, traffic during rush hour is manageable.

Hints and Tips

Your trip from O'Hare International Airport (ORD) to San Diego International Airport (SAN) should last about five hours. If you need an afternoon to acclimatize to the weather and time changes once you land, head over to the Tecolote Canyon Natural Park. The area is known for hosting many native and migratory birds.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.