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Spend the night-but don't sleep-in one of the city's five sexiest hotel rooms.

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Trump International Hotel & Tower
(401 N Wabash Ave, 312-588-8000)
The hotel Donald Trump’s hotels in Atlantic City may be decked out in over-the-top and—very unsexy—gold glitz, but the Chicago outpost is thankfully on the classy side. The condo-hotel’s lobby stays low-key, with few guests milling about. And who can blame them for wanting to stay in their rooms? The spacious suites (the smallest room is a respectable 600 square feet) feature kitchen space (with Sub-Zero fridges, Miele stove tops and espresso machines), comfy beds with 500-thread-count sheets and bathrooms featuring flat-screen TVs in the mirrors. And then there’s the view. Thanks to the curved building’s floor-to-ceiling windows overlooking the Chicago River, the lake, Tribune Tower and the El tracks on Wabash Avenue (to name a few sights!), there’s simply not a bad view in the joint.
The sexy side Yep, it’s all about that sexy view. The new Standard Hotel in New York is making headlines because uninhibited naked guests can often be seen lounging (among other activities) in the hotel’s crystal-clear floor-to-ceiling windows. If it weren’t for Trump’s reflective windows, we bet the same thing could happen here—but don’t let that stop you from trying.

Dana Hotel
(660 N State St, 888-286-2589)
The hotel An earth-toned palette and recycled materials (such as shards of beer bottles encased in the spa floor) lend an overall organic quality to this 216-room hotel, while details like exposed piping in the halls and graffiti-style “do not disturb” signs, designed by Miami Ink artist Ami James, present some urban flair. The place feels warm and calming, with lots of rounded edges, circular motifs and a flowing room layout. As for the guest rooms, each comes equipped with a sizable flat-screen TV and a souped-up media system where you can plug in your iPod.
The sexy side If you can, upgrade to the suite—the two-person shower with Italian tiles, rain-shower heads, three wall-shower jets and granite seating is splurge-worthy. And we haven’t even mentioned the views.

Park Hyatt Chicago
(800 N Michigan Ave, 312-335-1234)
The hotel Little expense has been spared at this 198-room Mag Mile property. The walls and hall are home to an estimated $23 million worth of artwork; and a scent expert created signature smells (the upscale scent of Indian green peppercorns and black pepper combined with just-picked, red habanero peppers) to waft through the modern lobby. The posh hotel’s black leather Eames chairs and 300-thread-count linens deliver style and comfort.
The sexy side Add the “butler bath” service to your room to kick things up a notch. When you opt for the “romantic” option, you’ll open the door to a candlelit guest room. Romantic music plays from the room’s sound system, and you’ll find a bubble bath drawn for two and a bottle of Champagne.

Ruby Room
(1743–1745 W Division St, 773-235-2323)
The hotel The steam shower (a shower that doubles as a steam room) alone warrants a splurge on one of the Ruby Deluxe suites at this spa’s neighboring B&B, but the king-size beds, topped with pillow-top mattresses and feather beds, and a minimalist yet inviting aesthetic (mostly cream color scheme and dark wood) lend a sense of luxury to each of the eight rooms. You won’t find a phone or TV in this joint; a stack of books (think a primer on healing crystals), a CD player and WiFi access provide the only in-room entertainment. It’s bring your own everything as far as food goes; the only edibles you’ll find in the economy-size kitchen are complimentary tea and coffee and other guests’ leftover booze. Luckily, options abound in this ’hood—from Alliance for coffee and croissants to Milk & Honey for lunch to Adobo Grill for dinner.
The sexy side In addition to the romantic patio out back and the utter peace and quiet the place provides, you and your honey can stop next door for a couples massage.

W Lakeshore
(644 N Lake Shore Dr, 312-943-9200)
The hotel Sexy is often one of the first words used to describe this clubby hotel. The 520 guest rooms boast sleek decor including teak furniture and dark red accents. And many of the rooms feature breathtaking views of the lake. As for activities outside your room, check out the indoor pool adjoining the outdoor sundeck, and visit Bliss Spa on the eighth floor for pampering from head to toe.
The sexy side Dance music pumps through the speakers in the lobby (and lobby bar area) and the black-clad staff members give guests a run for their money in an eye-candy contest. It’s such a sexy space that even if you book a single room, you might not be spending the night alone.

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