Chicago Hotels › Romantic Hotels
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The Waldorf Astoria Chicago

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 caters to leisure and business travelers. Sleek rooms feature neutral tones, contemporary furnishings, and 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

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-rated restaurant, to the big indoor pool, to bright fitness center, 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). Only The Peninsula and The Waldorf can compare.

JW Marriott Chicago

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 convenient for business travelers, and the pool and 24-four fitness center is top-notch.

Ritz-Carlton Chicago, a Four Seasons Hotel

Ritz-Carlton Chicago, a Four Seasons Hotel Rating: 4.5 Pearls

This 434-room hotel sits atop an upscale shopping mall right off the Magnificent Mile. The luxurious spa, the wonderful four-lane lap pool, the great design, and the outstanding address could make it one of the nicest hotels in town -- but the rooms fall a tad short — even after a multimillion dollar renovation in 2010 — with sophisticated but somewhat generic decor, some outdated amenities (such as CD players instead of iPod docks), and shower/tub combos in many bathrooms. The cuisine at the on-site brasserie doesn't wow, but the beautiful city views through its floor-to-ceiling windows do.

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago Rating: 4.5 Pearls

The 346-room Four Seasons Chicago is located on floors 32 to 46 of a limestone-and-glass skyscraper along the Magnificent Mile, atop an upscale shopping center. The hotel boasts a gorgeous indoor pool with a skylight and great views, an expansive spa and fitness center with modern machines, and a restaurant helmed by Michelin-star Executive Chef Kevin Hickey. Guest rooms boast phenomenal views, and were updated in 2012 with modern decor and art fixtures. It's one of the city's nicest hotels, and the location near the historic Water Tower and the Hancock Observatory can't be beat. But bathrooms -- most with shower/tub combos rather than separate walk-in showers and soaking tubs --are a tad less luxurious than you'd expect in this price range (though still lovely).

Millennium Knickerbocker Hotel Chicago

Millennium Knickerbocker Hotel Chicago Rating: 4.0 Pearls

The elegant 306-room Millennium Knickerbocker Hotel is a good value, considering its location half a block from the Magnificent Mile. It's true that the historic property doesn’t have many amenities (only a 24-hour fitness center and a 24-hour business center), and the rooms are on the small side — but they're nicer than those at the similarly priced Sutton Place, and come with big flat-screen TVs and Frette linens.

The Allerton Hotel Chicago

The Allerton Hotel Chicago Rating: 4.0 Pearls

The 443-room Allerton is one of the few hotels right on the Magnificent Mile, and its rooms -- with soothing blue-and-white color schemes, iPod docks, and flat-screen TVs -- are more modern and stylish than those at the neighboring Omni and Intercontinental hotels. But unlike its neighbors the Allerton lacks a pool, and its rooms offer significantly less space than the Omni's generic two-room suites.

The Talbott Hotel

The Talbott Hotel Rating: 4.0 Pearls

Built in 1927, the 149-room Talbott is an upscale boutique hotel that retains much of its original grandeur. Far from a dusty relic, the hotel and its large rooms combine antique English decor with modern technology, such as free Wi-Fi and the Apple Mac minis that function as sophisticated controls for the Internet ready 46-inch flat-screen TVs. With its Green-Seal certification, the hotel practices eco-friendly housekeeping and climate control. The ambience and consistently top-notch service fit right in to Chicago's posh Gold Coast neighborhood, with upscale shopping and dinning in every direction. Guests might also want to check out the nearby Whitehall Hotel, which has similar historical, boutique ambience.

The Drake Hotel

The Drake Hotel Rating: 4.0 Pearls

The 535-room Drake Hotel is a historic property on upscale Magnificent Mile and one of Chicago’s grande dames, with an impressive lobby full of chandeliers and a beautiful classic decor. Despite its historic status, modern amenities abound: There is a large, modern fitness center; wonderful dining options on-site, including the Palm Court, where a harp player entertains the guests during the afternoon tea; and even a shopping arcade with designer names like Chanel. But while the rooms are adequate and have some modern perks (like flat-screen TVs and MP3 players), the bathrooms are sub-par and could use an upgrade. The golden days of this luxurious property might be slowly fading, but it is still a great pick for its history and high-class notoriety.

Sheraton Chicago Hotel & Towers

Sheraton Chicago Hotel & Towers Rating: 4.0 Pearls

Designed as a downtown convention hub, the upscale Sheraton Chicago Hotel & Towers, with its massive event facilities, caters to business travelers and big groups staying for weddings or conferences. The rooms are large and business-friendly, with desks and work space, but the Wi-Fi isn't free. On-site restaurants, bars, a cafe, indoor pool, and even a full service FedEx office make it possible to attend an event and never set foot outside the hotel. But other guests can get lost in the shuffle among the events and the endless blocks of reserved rooms. With 1,214 rooms over 34 floors, housekeeping struggles to keep up. Families or couples looking for the conveniences of a big chain hotel from which to explore Chicago have better options, such as the Hyatt Chicago Magnificent Mile or the Radisson Blu Aqua Hotel.

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Oyster Pearl Rating

  • Award-Winning

What's Your Style?

  • Romantic
  • Luxury
  • Boutique
  • Business
  • Historic
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Locations

  • Gold Coast
  • Lakeview
  • Lincoln Park
  • Magnificent Mile
  • Oak Brook
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Amenities

  • Air Conditioner
  • Babysitting Services
  • Balcony
  • Basic Television
  • Business Center
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Brands

  • Hard Rock
  • Hilton
  • JW Marriott
  • Renaissance
  • Ritz-Carlton
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