21 days in San Diego Itinerary
21 days in San Diego Itinerary
Created using Inspirock San Diego vacation planner
Start: Chicago
Fly
1
San Diego
— 20 nights
Fly
End: Chicago
Sun, Dec 27 - Sat, Jan 16
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See full calendar
20
nights
20
nights

America's Finest City
Divided into neighborhoods with distinct characters and cultural heritages, San Diego sits just north of the Mexican border and offers visitors a blend of tourist attractions, including a lively nightlife, diverse cuisine, and a thriving musical scene.You'll visit kid-friendly attractions like San Diego Zoo and SeaWorld San Diego. You'll find plenty of places to visit near San Diego: Anaheim (Disney California Adventure Park, Tarzan's Treehouse, &more), Oceanside Pier (in Oceanside) and LEGOLAND California (in Carlsbad). And it doesn't end there: see the interesting displays at USS Midway Museum, appreciate the history behind Cabrillo National Monument, immerse yourself in nature at Torrey Pines State Natural Reserve, and stroll around Sunset Cliffs Natural Park.
To find traveler tips, where to stay, ratings, and other tourist information, use the San Diego road trip app.
Chicago to San Diego is an approximately 6.5-hour flight. You can also drive; or take a bus. You'll gain 2 hours traveling from Chicago to San Diego due to the time zone difference. Expect warmer temperatures when traveling from Chicago in December; daily highs in San Diego reach 68°F and lows reach 51°F. You will have some time to spend on the 16th (Sat) before leaving for home.
Things to do in San Diego
Side Trips
Find places to stay Dec 27 — Jan 16:
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