The Waldorf Astoria Chicago Rating: 5.0 Pearls
The Waldorf-Astoria offers top-of-the-line luxury in Chicago. With an intimate, boutique feel -- but all the amenities of a large hotel -- the 188-room Waldorf is a premier pick for romance. Sleek rooms feature neutral tones and contemporary furnishings; some have gas fireplaces. Gorgeous marble bathrooms that offer separate showers and soaking tubs, as well as TVs inset in the mirrors. Highlights include the upscale restaurant Balsan, a top-notch spa, and health club with extensive services and an indoor lap pool. Plus, the hotel's location in the swanky Gold Coast neighborhood puts it within walking distance of upscale shops, restaurants, and attractions.
Trump International Hotel & Tower Chicago Rating: 5.0 Pearls
This 339-room Trump is one of the top luxury hotels in Chicago, located in a modern glass tower right on the Chicago river and within easy walking distance of the Magnificent Mile. The sleek, glossy decor is subdued and tasteful, and every amenity -- from the Michelin-starred restaurant, to the big indoor pool, to the spa -- is first-rate. The huge, tasteful rooms have limestone bathrooms with soaking tubs and floor-to-ceiling windows (often with phenomenal views).
Dana Hotel and Spa Rating: 4.0 Pearls
This 216-room hotel is an urban retreat with zen decor, a spa, a stylish restaurant, and popular lounge, located three blocks from the Magnificent Mile. The hotel's serene vibe continues into the luxurious rooms, which feature hardwood floors, large, spa-inspired showers, plush beds, and floor-to-ceiling windows or balconies. It's one of Chicago's most luxurious boutiques.
Villa D' Citta Rating: 4.0 Pearls
The six-room Villa D’ Citta is a cozy, romantic bed-and-breakfast located in residential Lincoln Park. Its few features are all charming: an outdoor whirlpool and sun deck, a brick courtyard with a barbecue, and a large communal kitchen. The bright, luxurious rooms have big flat-screen TVs and hardwood floors, but two of them share a bathroom.
JW Marriott Chicago Rating: 4.5 Pearls
Opened in late 2010, this upscale hotel is housed in a historic neoclassical-style building with crystal chandeliers and a grand staircase in the lobby. But sophisticated rooms are thoroughly modern, and big, elegant bathrooms have separate showers and soaking tubs. The Loop location is ultraconvenient, and the spa is top-notch.