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, $148 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 $108 per night from Mar 21 to Mar 22
$108
per night
Mar 21 - Mar 22
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 clean rooms in our reviews. ...
8.2/10 Very Good! (1,004 reviews)
Good stay
"Nice hotel for the price with friendly staff!"

Reviewed on Mar 16, 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 $87 per night from Mar 20 to Mar 21
$87
per night
Mar 20 - Mar 21
Stay at this business-friendly hotel in San Diego. Enjoy free parking, WiFi, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms ...
5.8/10 (2,018 reviews)
Keep Up the Good Work
"check in was easy as always. All of the staff all the way down to housekeeping are great! I love the way they are upgrading everything in the rooms and the laundry room. New vending machines and microwaves are all good. I love the progress to make the customer more comfortable"

Reviewed on Mar 16, 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 $101 per night from Apr 1 to Apr 2
$101
per night
Apr 1 - Apr 2
Stay at this hotel in San Diego. Enjoy free WiFi, 2 restaurants, and breakfast. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
8.6/10 Excellent! (2,599 reviews)
"This is an older hotel. My room was clean and the bed was good, too. I didn’t use the pool, but it looked nice. They charge $15 a day parking which is BS. Two restaurants. One breakfast one dinner. I ate at both and they were quite adequate. The property was dated but well kept. Kitschy."

Reviewed on Mar 17, 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
23
Earliest Flight Departure Date
Mar 26
Latest Flight Departure Date
Mar 27
Popular Airlines
United 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.