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 ($81 One Way, $163 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, 92117
The price is $120 per night from Sep 5 to Sep 6
Stay at this business-friendly hotel in San Diego. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
4.1/5 Very Good! (1,002 reviews)
"We stayed there only 1 night, Very clean, quiet and nicely updated, Air condition was working very good, nice and hot shower and pressure. The only small problem we had which I am sure they will fix this problem is that the Coffee cups wouldn’t hold the coffee and they start leaking immediately. ..."

Reviewed on Aug 10, 2022

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, 92110
The price is $69 per night from Aug 14 to Aug 15
Stay at this business-friendly hotel in San Diego. Enjoy free parking, WiFi, and a spa tub. Our guests praise the overall value in our reviews. Popular attractions ...
2.7/5 (1,554 reviews)
"Courteous Staff. Drive and sidewalks are a bit stained with soda and garbage dumpster is always overflowing. Yet worth the price and the small qaint place is comfortable."

Reviewed on Aug 5, 2022

E-Z 8 Motel Old Town
Kings Inn San Diego

Kings Inn San Diego

2.5 out of 5
1333 Hotel Cir S, San Diego, CA, 92108
The price is $96 per night from Sep 6 to Sep 7
Stay at this hotel in San Diego. Enjoy free WiFi, 2 restaurants, and breakfast. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions ...
4.2/5 Excellent! (2,248 reviews)
Family fun!
"Great family hotel. Love the saltwater pool and not stinking like chlorine all day. The staff is super friendly and helpful also. We ate at the Waffle Spot it was great and reasonably priced."

Reviewed on Aug 11, 2022

Kings Inn San Diego
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.

Fly From Chicago to San Diego

Origin Chicago
Destination San Diego
Number of Daily Flights 33
Earliest Flight Departure Date Aug 20
Latest Flight Departure Date Aug 21
Popular Airlines American 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.