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 ($59 One Way, $118 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 $116 per night from Nov 26 to Nov 27
$116
includes taxes & fees
$103 per night
Nov 26 - Nov 27
Stay at this hotel in San Diego. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the convenient parking in our ...
8.2/10 Very Good! (1,004 reviews)
"Good location and convenient access to freeway."

Reviewed on Nov 20, 2024

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 $83 per night from Nov 25 to Nov 26
$83
includes taxes & fees
$74 per night
Nov 25 - Nov 26
Book a stay at this business-friendly hotel in San Diego. Enjoy free parking, WiFi (surcharge), and a 24-hour front desk. Our guests praise the helpful staff ...
6/10 (2,033 reviews)
"Cool little hotel with very spacious rooms. We really liked this place alot"

Reviewed on Nov 20, 2024

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
The price is $96 per night from Nov 27 to Nov 28
$96
includes taxes & fees
$86 per night
Nov 27 - Nov 28
Stay at this hotel in San Diego. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (3,028 reviews)
"Pool and jaccuzi are excellent. 15$ parking fee seems a bit crazy. Should be included."

Reviewed on Nov 22, 2024

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
Earliest Flight Departure Date
Latest Flight Departure Date
Popular 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.