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Lowest round trip fares by airline from Chicago and San Diego

Cheapest prices ($28 One Way, $49 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
2.5 out of 5.0
4.1 out of 5 (7 reviews)

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 ...

It was nice and clean the staff were very nice I would come back.
  
E-Z 8 Motel Old Town
2.5 out of 5.0
2.5 out of 5 (6 reviews)

Located in Mission Valley, 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 ...

Hdmi outlet didnt work Internet is 5.99 should be free
  
Kings Inn San Diego - Seaworld - Zoo
2.5 out of 5.0
4.2 out of 5 (12 reviews)

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 ...

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!
  

Flights Review

Dec 24, 2019

No WiFi, seat stiff, upright and unmovable. Makes for a long 4 hour flight.

Dec 19, 2019

Awesome flight

Dec 1, 2018

Love this airline

Sep 19, 2018

The power outlet under my seat didn’t work and there’s was a short delay. But other than that the flight was great

Aug 29, 2018

Everything went well and Im happy to be home. I will defend fly United again.

Jul 30, 2018

The flight attendants on both flights that were covering the back of the plane (where I was sitting) were wonderful. Very helpful and friendly. I had two kids so little things help. Lifting arm rest, making sure we had drinks when we woke up, so friendly.

May 6, 2018

Landed in one piece, all good.

May 2, 2018

Good flight

Mar 29, 2018

had bought new luggage for this trio when I received it from United upon arrival at San Diego I international airport it was all disgusting and dirty

Fly From Chicago to San Diego

OriginChicago
DestinationSan Diego
Number of Daily Flights6
Earliest Flight Departure DateDec 8
Latest Flight Departure DateDec 9
Popular AirlinesUnited Airlines

Cheap flights from Chicago to San Diego

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.