9. Chicago, Illinois
The Midwest’s greatest metropolis is famously unpretentious, but also underrated for romance. Outstanding music festivals, a sensational Lake Michigan waterfront, and world-class museums, theaters, and gardens—not to mention such soul-nourishing fare as deep-dish pizza and decked-out dogs—make Chi-Town an awesome choice for a sweethearts’ idyll.
AAA Diamond Recommendation: The luxury riverside hotel of The Langham (which enjoys a AAA Four Diamond designation) has everything you need for a romantic escape in the Windy City, from its exquisite Chuan Spa to the private haven of your guest room, featuring granite, travertine, and marble elements, a rainfall shower, and a soaking tub.