Chancellor Hotel on Union Square

This family-run, 137-room hotel is another historic gem that’s withstood the test of time. When it was built for the Panama Pacific International Exposition of 1915, it was deemed the tallest hotel in San Francisco. Today, the hotel is rooted firmly in the present, offering free HBO and mini-fridges. The rooms are compact, but cozy, with ivy-green walls and warm mahogany headboards. (One space that exceeds expectations is the oversized tub.) Proper attention is paid to a good night’s rest here: Peruse the hotel’s complimentary pillow menu, which offers a dozen poufs of varying firmness. Breakfast is served all day at the hotel’s Lucques Restaurant—opt for the benedict.