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.

Tue, Jan 14 - Thu, Jan 23
MDW
Chicago
SAN
San Diego
$118 Roundtrip, found 1 hour ago
$118
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Jan 14 from Chicago to San Diego, returning Thu, Jan 23, priced at $118 found 1 hour ago
Sat, Jan 4 - Wed, Jan 8
ORD
Chicago
SAN
San Diego
$118 Roundtrip, found 6 days ago
$118
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Jan 4 from Chicago to San Diego, returning Wed, Jan 8, priced at $118 found 6 days ago
Thu, Dec 12 - Mon, Dec 16
ORD
Chicago
SAN
San Diego
$165 Roundtrip, found 19 hours ago
$165
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Thu, Dec 12 from Chicago to San Diego, returning Mon, Dec 16, priced at $165 found 19 hours ago
Wed, Feb 26 - Wed, Mar 5
ORD
Chicago
SAN
San Diego
$302 Roundtrip, found 4 days ago
$302
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Wed, Feb 26 from Chicago to San Diego, returning Wed, Mar 5, priced at $302 found 4 days ago
Tue, Dec 24 - Tue, Dec 31
ORD
Chicago
SAN
San Diego
$403 Roundtrip, found 23 hours ago
$403
Roundtrip
found 23 hours ago
Select United flight, departing Tue, Dec 24 from Chicago to San Diego, returning Tue, Dec 31, priced at $403 found 23 hours ago

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 Dec 23 to Dec 24
$116
includes taxes & fees
$103 per night
Dec 23 - Dec 24
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! (1,006 reviews)
"Central location to everything we needed. Rooms were clean and staff were professional and friendly. We would come back again."

Reviewed on Nov 25, 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 $90 per night from Nov 28 to Nov 29
$90
includes taxes & fees
$80 per night
Nov 28 - Nov 29
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 (2,037 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 $107 per night from Dec 1 to Dec 2
$107
includes taxes & fees
$95 per night
Dec 1 - Dec 2
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! (3,039 reviews)
Nice for the price
"We forgot to ask if there was an elevator and sure enough our room was on the upper level. They did have a freight elevator and a maintenance worker delivered our bags to our room for us. There was no microwave BUT there was a really nice refrigerator with separate door freezer. This hotel has far ..."

Reviewed on Nov 24, 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.

Flights from Cities near Chicago

Flights to Cities near San Diego

Other Flights to San Diego

Other Flights from Chicago

*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.