Amalfi Hotel Chicago
20 W. Kinzie St.
Chicago, IL 60610
(312) 395-9000
http://amalfihotelchicago1-px.trvlclick.com
Scores of swank hotels call River North home, but Almafi sets itself apart by offering guests something (or rather someone) who can make or break their time in Chicago: an Experience Designer. This individual is a concierge of coolness, if you will, as Amalfi bills the perk as someone who "can always set you up at the best tables at the hottest new restaurants or get you on the list to the trendiest clubs." Best, hottest, trendiest? That’s a whole slew of adjectives that often don’t mean jack, but with amenities like pillow-top mattresses, 316-thread count Egyptian cotton sheets, multiple shower heads and gratis Aveda products, the hotel does its best to live up to the talk.

Conrad Chicago
521 N. Rush St.
Chicago, IL 60611
(312) 645-1500
http://conradhotels1.hilton.com
The Conrad seems to be proving its worth in high-tech devices by plopping Bose entertainment systems, 42-inch plasmas and iPod alarm clocks in every room. Still, it’s got plenty of other selling points: 500-thread count linens, oversized bathrooms with deep tubs and marble vanities big enough for a couple’s sundries and then some, killer views of the city and a location near the Mag Mile. The rooms mix modern design elements with retro-inspired pieces, giving an overall hip feel but not a hoity toity one.

The Drake
140 E. Walton Pl.
Chicago, IL 60611
(312) 787-2200
http://www.thedrakehotel.com
Anyone who’s ever cruised south down Lake Shore Drive can recognize the striking façade of this classic hotel. Open since 1920, the Drake has welcomed travelers looking for a bit of old-fashioned elegance in the heart of Chicago’s fanciest shopping district. The hotel itself shares space with the likes of Chanel, and guests who don attire from the posh boutique will feel right at home sipping afternoon tea in the Palm Court Lounge. While there are a few modern amenities here, like a fitness room and high-speed Internet, the overall effect is that of old-school high-end living; the guest rooms are decidedly timeless, with dark-wood furnishings, crisp white linens turned down nightly and dramatic draperies.

Fairmont Hotel Chicago
200 N. Columbus Dr.
Chicago, IL 60601
(312) 565-8000
http://www.fairmont.com
If you judge hotels based on what kind of wheels they provide, put the Fairmont at the top of your list. It offers a chauffeured Bentley to shuttle guests to and fro, but with a restaurant-like aria on its premises, why leave? The inventive eatery has one of the finest sushi bars in town, and dishes up plates like barbecue duck with lobster chow mein and grilled pacific escolar with tomato-avocado salsa. Fill up your belly and then have someone else fill up the tub for you: Fairmont offers a service called Serenity Bath, a luxurious treatment involving relaxing, aromatic fragrances. Pair that with an insanely spacious room, and you’ll never want to leave.

The Four Seasons
21 S. Clark St.
Chicago, IL 60603
http://www.fourseasons.com
The indoor pool at Four Seasons looks straight out of a Roman palace, with white pillars, gilded accents and a glass dome. Even so, perhaps the most appealing aspect of the hotel is its height; all guest rooms have views of Lake Michigan or the skyline from the 32nd to 46th floors. For people who spoil themselves to the point of staying in this kind of luxury, they'll no doubt want to partake in the hotel's intense spa treatments. Ever wanted to rub your face in caviar and pearl proteins? Check. How about wrapping yourself in a honey, Maui cane sugar and Hawaiian oil treatment? They've got that, too. The Seasons restaurant feels a bit uppity, with burgundy carpet, stiff grey chairs and ornate chandeliers; still, it'll serve an incredible prix fixe meal that, not surprisingly, changes with the seasons ... all four of them.

Hard Rock Hotel
230 N. Michigan Ave.
Chicago, IL 60601
(312) 345-1000
http://www.hardrockhotelchicago.com
High-rollers with a penchant for rock 'n' roll will feel right at home at Hard Rock. The guest rooms beg for a little rocker bad boy trashing, with their zebra print accents, leather furnishings and chrome nightstands. You’ll go to bed with celebs like Mick Jager or Jimi Hendrix standing over you, as the decor pays homage to lauded musicians. A home theater system, 27-inch flat screen and feather-top bedding round out the room amenities. Before checking out, be sure to sip a saketini at China Grill, the hotel’s swanky eatery, or opt for a brew at Base, a sleek lounge that even feels clubby in the afternoon.

Hotel Allegro
171 W. Randolph St.
Chicago, IL 60601
(800) 643-1500
http://www.allegrochicago.com
Boutique hotels have to find a way to compete with corporate behemoths like Hilton and Marriot. Hotel Allegro throws its hat into the ring by offering guests something chain hotels can’t pull off as well: personalized packages. With themes ranging from an eco-friendly stay that supplies you with organic snacks and parking for your hybrid to one titled Wild Night, with an in-room cocktail party, VIP access to clubs and a morning after basket outfitted with a baseball cap and eye mask, the packages offered here allow each guest to build a trip that caters to their needs. No matter which experience they choose, all visitors will enjoy spacious, Art Deco-inspired rooms with oversized towels, Mp3 players, on-demand movies and views of the Chicago River. Allegro even offers a couple theme suites, including one that honors the infamous Second City Theatre with design input from cast members.

Hotel Blake
500 S. Dearborn St.
Chicago, IL 60605
(312) 986-1234
http://www.hotelblake.com
When James Beard Award-winning Shawn McClain heads a hotel’s restaurant, it’s only natural the rest of the experience will match his caliber of excellence. The building, which reopened as Hotel Blake in 2005, dates back to the 19th century and is located in Printer’s Row, which was once home the city’s printing and publishing industry. The loft-like qualities of the chic rooms, with high ceilings, red and grey accents and dark-wood touches, give the hotel a decidedly modern feel, though it remains entirely accessible.

Hotel Sax
333 N. Dearborn St.
Chicago, IL 60607
(312) 923-2458
http://www.hotelsaxchicago.com
The House of Blues Hotel decided to begin its swanky makeover with an appropriately hip name: Hotel Sax. The rooms mix romantic touches, like silk pillows and tasteful flower accents, with clean, sleek lines and edgy pieces (think quilted leather headboards). Packages like “Rock Like the Red Hot Chili Peppers,” which fills the suite with tube socks (a la the band’s almost-nude performances), an acoustic guitar, Heineken products and a juice bar attended to by a “professional” smoothie-maker, prove the hotel hasn’t forgotten its rocker roots. Still, the new on-premise Crimson Lounge feels more appropriate for the cast of “The Hills” than for a grizzled old blues guitarist. It even emits a signature scent, a mix of patchouli, cinnamon and nutmeg, in the Victorian-inspired environs. Nevertheless, it puts a fitting finishing touch on the hotel’s too-cool-for-school renovation.

The James Chicago
55 E. Ontario St.
Chicago, IL 60611
(877) JAMES-55
http://www.jameshotels.com
The James Hotel fits into its posh, near Mag Mile surroundings with a sleek-as-can-be interior. The guest rooms, which range from studios to apartments complete with dining rooms, have an Asian-inspired feel, but also incorporate uber-modern touches like plasma TVs, high-end stereo systems with iPod dock stations and clean-lined designer furniture. The in-hotel David Burke’s Primehouse, serving dry-aged Blank Angus cuts, offers a different take on steak than at old-school Chicago chops spots. The accompanying J Bar is drippingly hip, with glossy banquettes, mirror-lined walls and martinis that’ll leave you with a staggering bar tab, thanks to their addictive-pricey one-two punch.

Park Hyatt Chicago
800 N. Michigan Ave.
Chicago, IL 60611
(312) 335-1234
http://parkchicago.hyatt.com
The Park Hyatt is a pampering fiend’s paradise, with its oversized tubs and marble baths in every room, not to mention the Tiffany Kim Institute Spa awaiting your facial, waxing and massage service needs. Though it’s stereotypically the ladies who like to take relaxing bubble baths, the guest rooms are simple and masculine, with modern furnishings, crisp, no-frills white linens and window seating. The lobby boasts an original painting by Gerhard Richter, but perhaps the most impressive art on display is at the hotel’s restaurant, NoMI; though the Asian-inflected seasonal plates could be considered art in their own right, it’s Dale Chihuly’s stunning glass sculptures that compete for your attention.

Peninsula Chicago
108 E. Superior St.
Chicago, IL 60611
(312) 337-2888
http://chicago.peninsula.com
Having tea at the Peninsula can make any lady feel like a queen. But for all the opulence of The Lobby, a gilded space with 20-foot windows, striking white pillars and detailed wood floors, the guest rooms are conversely quite simple, though no less beautiful. The color scheme skews toward the soothing, with pale shades (think beige-and-white striped draperies and ivory accents) dominating the décor. Amenities include plush furniture, marble bathrooms with soaking tubs, 27-inch Sony flat screens, luxurious bathrobes and DVD players. Most rooms have separate seating areas and some even let you cozy up in front of a fireplace. If you don’t make it to tea, there’s still hope for a gastronomic delight with a dinner reservation at the award-winning Avenues restaurant, which dishes up prix-fixe feasts that will set you back no less than a Benjamin.

Sofitel Chicago Water Tower
20 E. Chestnut St.
Chicago, IL 60611
(312) 324-4000
http://www.sofitel.com
With locations in Dubai, Beijing, Paris, Vienna and other world-class cities, Sofitel brings an international flair with a touch of European modernity to Chicago’s hotel scene. The rooms come furnished in sleek, designer couches that look like they belong in contemporary art galleries, roomy bathrooms outfitted with luxurious robes by Frette, low-slung platform beds made from light African woods and soft lighting matched with stunning views. Still, the rich interior gets dwarfed by the striking glass and steel exterior by Jean Paul Viguier; the façade, which calls to mind an inverted ship mast rising from the sea, won the American Institute of Architects' "best new building in Chicago in the last 10 years" award in 2004. With digs like these, you can’t help but feel glamorous as you hang in the lobby dotted with mauve accents or nibble on French fare at Cafe des Architectes.

Swissotel Chicago
323 E. Wacker Dr.
Chicago, IL 60601
(312) 565-0565
http://www.swissotel.com
Swissotel is kind of like the Holiday Inn of high-end hotels; it’s the kind of hotel you can picture in just about any American city with a decent-size downtown, though, to be fair, the modern plush furnishings (think stuffed, not stuffy) sure beat the heck out of a Holidome in terms of style. Chicago’s version of the Euro hotel offers one of the best locations view-wise in the city, as it sits at the end of Wacker and is made entirely of glass, resulting in unobstructed shots of Lake Michigan and, for true blue travelers, Navy Pier. Most of the rooms average about $200 per night, but you can upgrade to a 1,200-square-foot suite with killer panoramic city snapshots and a heftier price tag. The Swissotel also boasts a heated Olympic-size indoor pool and a spa and gym on the penthouse level, which, come to think of it, certainly eclipse the Holiday Inn’s handful of shoddy treadmills and five-foot deep waters.

W Chicago Lakeshore
644 N. Lake Shore Dr.
Chicago, IL 60611
(312) 943-9200
http://www.starwoodhotels.com
With room categories like Wonderful, Spectacular, Fantastic, Marvelous and—we’re not kidding—Extreme Wow, this Gold Coast hotel seems fit for a clientele of, like, totally cool sorority girls. Or, maybe the Starwood Hotel folks are just telling it like it is? After all, the Fantastic guest room, with two bedrooms, a separate entertainment area, three plasma TVs, featherbeds, a bright, modern decor and three baths, is, well, pretty darn fantastic. The on-premise Bliss spa, rooftop lounge, Waves seafood restaurant and location on the lake adds to the hotel’s heavenly hip vibe, not to be outdone by the enormous, almost menacing looking, tilted “W” logo awaiting visitors out front.