Southwest® flights from Chicago (O'Hare) to San Francisco from $114

When you land in the San Francisco Bay Area, you may have a tough time deciding where to start your Frisco adventure. Whether you’re drawn to the area because of its rich counterculture history or its importance to the modern tech world, there’s plenty to explore. Consider starting with something you can’t get anywhere else: a cable car ride up iconic Nob Hill then down to the waterfront. Hills abound in San Francisco—there are 44 across the city that make up its distinctive terrain. If you rent a car, don’t forget to set your parking brake.

You can’t visit Frisco without exploring Golden Gate Park. The largest park in the city stretching from city center to the ocean, it’s larger than famed Central Park. The grounds include the Conservatory of Flowers, the Japanese Tea Garden, and the San Francisco Botanical Garden. North of the park is the Golden Gate and the famed Golden Gate Bridge—stop by the visitors center and consider taking a walk across the bridge into Marin County.