Assuming its recession-ready prices hold steady (we've seen rates as low as $150), this outpost of the five-hotel Affinia chain located a block off North Michigan Avenue is one of the best values in town. True, the spartan reception area feels understaffed, and the Marcus Samuelsson C-House restaurant demonstrates that celebrity chefs can oversee too many kitchens. But the $25-million renovation completed in June 2008 clearly shows in the guest rooms, which are done up in a vaguely Deco style with a silver and gold palette and padded leather headboards. While standard rooms are a respectable 390 square feet, it's worth "splurging" for one of the 715-square-foot junior suites ($199). The bathrooms are small, but the hotel aims to compensate with flat-screen TVs and an inventive range of free amenities, including a stay-fit Experience Kit (complete with yoga mat and workout bands) and a pillow menu (try the "sound pillow," threaded with thin white-noise speakers). There's also a fitness room, which comes in handy after indulging in the "Sweet Treats" dessert and candy room-service menu. Bargain-hunters may find the Affinia's dogged attempt to show guests a playful time to be a bit much, but you have to credit the hotel's creative ambition. —Raphael Kadushin

Don't be put off by pretension at this River North hipster hotel. The often black-clad staff is eager to please, from the "experience designer" who checks you in (and can score you seats at the area's hottest restaurants) to the "maestro" (a.k.a. general manager), who sometimes presides over happy hour with free top-shelf drinks. All 215 rooms have fluffy pillowtop mattresses, Aveda toiletries, multihead showers, Egyptian-cotton sheets, flat-screen TVs, as well as marble or granite bathrooms. There are lots of freebies too: buffet-style continental breakfast, access to a CD library, high-speed Internet (both wired and Wi-Fi), and local phone calls.

Given its location a half block east of North Michigan Avenue, where $300 is the low-end norm for a room, the Avenue is notable for its easy-on-the-wallet rates, which can start at $199 for a double on weekend nights. All 350 rooms have flat-screen TVs and free Wi-Fi, the smallest are a respectable 300 square feet, and those on the top floors have stellar Gold Coast views. The squat furniture, mud-brown palette, and small bathrooms leave much to be desired, and while the signature zebra-print chairs don't suit our taste, they're a lively signal of environmental awareness. (The hotel has adopted a Grevy's zebra, an endangered species, at the Lincoln Park Zoo.) The best bet for a business traveler is an iMac- and color printer–equipped Tech Room; parents can opt for a Kid-Friendly Room, which includes rainbow-colored quilts and a Wii game system. Light sleepers should be aware that hallway noise can be problematic—not all guest room doors fit their door frames properly—and some AC units rumble like a moped. However, things improve outside the rooms: There's a cocktail and tapas lounge on the 40th floor, a rooftop pool, and an Elephant & Castle outpost that serves shepherd's pie and fish and chips. Overall, the Avenue doesn't quite deliver a polished designer experience, but with savings like this, what did you expect?

After a $128 million restoration (and a decade of legal wrangling), the historic Blackstone has emerged as the swankest hotel in Chicago's revitalized South Loop, convenient to Millennium Park, the Art Institute, and the theater district. Behind the redbrick, white stucco, and green copper Beaux Arts exterior are 332 updated rooms whose masculine red, black, and beige decor features Eames chairs and original works by contemporary Windy City artists. In place of the usual tourist bedside reading, the culturally attuned management provides books by local authors, including social histories of the Chicago blues and witty biographies of Chicago firehouse dogs. The lively in-house restaurant, Mercat a la Planxa, dishes up exquisitely presented (and reasonably priced) Catalan grills, tapas plates, and wine flights, conceived by Chicago-born chef José Garces.

Hyper-stylish and bathed in natural light and textures, most rooms in the 26-story high-rise have floor-to-ceiling windows lasciviously exposed (should you opt not to use the blackout curtains) to neighboring offices and condos. The vibe is simultaneously spare and plush, with industrial-cement ceilings, ribbed wallpaper, indecently comfortable beds, and metallic velour textiles. All rooms have spa-inspired bathrooms and the latest gadgetry, including fully stocked wine chillers. The spa, booked solid on weekends, offers a greatest hits menu of moderately priced massages, facials, and wraps. The Dana has a choice location between North Michigan Avenue and the River North dining and gallery district, but reserve a table if you want to go to its duplex steak and sushi restaurant, Ajasteak, a new neighborhood hot spot. The rooftop Vertigo Sky Lounge has a glassed-in bar and an outdoor fire pit where the city's remaining smokers can light up with impunity.

For a taste of the high life at down-to-earth rates, book a room at this charming mansion with a chichi Gold Coast address. Owners Mike Maczka and Tom Warnke restored the 1892 row house to its original state in 1997. Many details remain, including the beautiful exterior (an example of Flemish Revival architecture, from which the B&B takes its name). Apartment-sized units (studios and one-bedroom suites) feature all the comforts of home: down comforters, cordless phones with answering machines, cable TV, DVD player, Wi-Fi, and fully stocked kitchens. Each unit is fitted out in an English Arts and Crafts motif, with fireplaces, inlaid wood floors, high ceilings, and decorative moldings.

The Four Seasons looms above the toniest stretch of N. Michigan Avenue in one of the country's tallest limestone buildings. Though the stature and location are grand, this is the city's most discreet luxury hotel, with its lobby tucked up on the seventh and eighth floors. And the 343 guest rooms are even more removed—they're on floors 30 through 46. They all have sweeping views of the city, but if you're willing to pay a bit extra, you can also look over the lake. More importantly, all the rooms are undergoing a $30-million renovation that will be completed in 2009. Nearly 300 of the guest rooms are already flaunting the new look, which swaps the former English-manor, high-tea decor for a forties, French cocktail party effect. That means Cubist artwork and curving Deco lines all laid out in your choice of two palettes: a cool blend of steel and oceanic blue or a warm scheme of chocolate browns and shimmery silvers. Both schemes feature upgraded bathrooms of hand-cut Chinese marble as well as fully modernized amenities, including LCD flat-screen TVs, Wi-Fi, and iPod docking stations upon request.

Channel your inner Hendrix at this way-cool 381-room Loop boutique, aptly located in a champagne-bottle-shaped Art Deco high-rise. Pictures of Bowie, the Beatles, Madonna, and other rock legends line the walls and hallways of this Daniel Burnham-designed tower. Rooms have teak-style furnishings, plasma TVs, DVD players, and lots of black, grays, glass, and mirrors. The purple-upholstered faux Barcaloungers are a great place to kick back and practice air guitar. Party into the wee hours at the hotel's Base Bar, then sleep off the hangover in a comfy feather bed. For the best views, book one of the Hard Rock rooms. The popular pan-Asian China Grill is in the lobby.

For a historic stay with a dash of flash, the Burnham is the place. Named for famed Chicago architect Daniel Burnham, this 122-room Kimpton boutique hotel is tucked into a landmark former office building (one of the city's first skyscrapers) with a prime State Street address, across from Macy's. Many of the structure's original details—marble wainscoting on ceilings and walls, terrazzo floors, mahogany trim, and ornamental elevator grills—were preserved during the 1999 renovation. Clubby, European-style guest rooms, once the building's offices, are splashed in gold and navy blue with velvet headboards, sateen bedspreads, and mahogany writing desks. Rooms on the northeast corner have the best views. Its Atwood Café has delicious comfort food—go for one of the signature pot pies. Pets are welcome.

Part of a midpriced boutique chain launched by InterContinental Hotels, the Hotel Indigo has an exuberant Margaritaville-meets-Nantucket design theme. The color-splashed lobby is decked out with oversize Adirondack chairs and a circular check-in desk that resembles a concession stand, but even that doesn't prepare you for the fun-house guest rooms. A typical room includes a blue phone, seashell-shaped light fixtures, whitewashed cupboards and headboards, and a small bathroom with a candy-colored shower curtain (no tubs) and Aveda products. The Golden Bean café on the ground floor dishes up salads and sandwiches, as well as a slight break from the over-the-top decor—if you want to maintain the color scheme, order the Peruvian blue corn chips with blue cheese dip. The playful Indigo also observes the seasons by shifting to different palettes (expect your room key and the lobby decor to be red, rust, or orange in the fall), but the year-round affordable rates (starting at around $250 or so on weekends) and the location on a leafy Gold Coast side street are the real draws.

More is more at Chicago's new music industry hot spot (formerly the House of Blues hotel), extroverted both stylistically and socially. A neighbor to the iconic 1964 Marina City (a.k.a. The Corncobs), Sax banishes the minimalism that has given design hotels a cold name, substituting a rococo sense of style in its 353 rooms: snakeskin wingback chairs, paisley-embossed leather headboards, and painted silhouettes of phantom chandeliers. Though the service is uniformly helpful and frequently enthusiastic, the Sax is not a place to cosset yourself away in your room. The House of Blues club next door ensures a steady stream of performers, as well as roadies and managers, creating a high-energy scene in the lobby, with its glass columns and check-in desks. Club patrons and hotel guests congregate in the lounge, Crimson, perching on a tufted red leather couch under a deer-antler sconce. For guests only, there is also a groovy technology lounge stocked with laptops, video games like Guitar Hero, downloadable music, movies, and HDTV screens, which are wired together so that Xbox players can face off from across the room.

Partners Danny Errico (owner of the Equinox fitness club chain) and Brad Wilson (co-founder of the W hotel chain), along with restaurateur Stephen Hanson and architect Deborah Berke, pulled off a nifty trick when they opened this property in April 2006. Together, they've created a downtown hotel that is both stylishly luxurious and a showcase for eclectic artwork. The airy lobby and guest rooms double as galleries for local up-and-coming modern artists, and even the enclosed courtyard has been turned into a video-projection exhibit space. The 297 rooms are decorated in earth tones and modernist furniture, with 42-inch plasma TVs and iPod docking stations. Some have nooks with king-sized daybeds; others have projection DVD players and surround sound. The hotel is home to David Burke's Primehouse, an outpost of the nouveau steak house in New York City, as well as a small spa, a gleaming gym, and the adjacent J Bar, which has quickly become one of the trendiest bars—hotel or otherwise—in town.

Other high-end Michigan Avenue hotels take a staid approach to luxury, but the Park Hyatt adds a running note of playful artistry and unabashed flamboyance. The hotel's art collection, selected by local curators, turns your room into a private gallery; the specially commissioned photos of Chicago complement a masculine mix of cherrywood and black leather Eames chairs. The aesthetic continues in the wildly popular NoMI, which draws locals with its whimsical takes on Japanese-influenced French cuisine and a Tony Chi design showcasing Alice in Wonderland-esque Chihuly chandeliers amid leather-wrapped beams. Book a room on the east side, where sliding doors between the bath and bedroom allow you to survey Lake Michigan from the comfort of your oversize marble soaking tub.

The 339 rooms at this swank Gold Coaster, aptly located next to Tiffany, are patrician and huge (the smallest start at 530 square feet). Avoiding flash for understated glamour, they glow in a fitting palette of soft golds. The sense of luxury follows you into the marble bathrooms, which include in-tub TVs, hands-free phones, a soaking tub, and a separate shower. Tech-friendly features range from complimentary Wi-Fi to a multifunction bedside control panel that adjusts temperature, lights, and curtains, meaning you'll never have to get out of bed. The penthouse spa and its mammoth lap pool, though, will probably get you moving. So will the Peninsula's four restaurants, including the acclaimed Avenues (now helmed by chef Curtis Duffy) and the Chinese jewel-box Shanghai Terrace (dine alfresco in the summer). And then there's the weekly calendar of food events: A Thursday ice-cream social stars sundaes, Key lime parfaits, and dreamsicles; afternoon tea gets a fashionable update on Fridays; and a weekend chocolate bar transports you to a candy-land fantasia.

Set right above Water Tower Place in the heart of the Gold Coast, Chicago's Ritz-Carlton (which is owned and managed by the Four Seasons) has been around since 1977. But after a multimillion-dollar renovation completed in spring 2009, you'd never guess that it's one of the country's oldest Ritz hotels: In guestrooms equipped with Wi-Fi and flat-screen TVs, an updated ensemble of dark wood furniture, white linens, graphic wall coverings, and photos of Chicago architecture has replaced the former chintz-and-brocade look. The 525 rooms, located on floors 15 to 29, are slightly bigger and higher-ceilinged than those at the Four Seasons, and the place has the concept of service down to a science. Phone messages are hand-delivered; kid-friendly items, from toys to PlayStation consoles, are ferried to the rooms of travelers with children. The staff also keeps a stockpile of necessaries on hand for adults, including curling irons and even cummerbunds for forgetful groomsmen. There's a modern in-house spa, but the best pleasures here are still the old-fashioned ones, like taking English afternoon tea in the magnificent greenhouse lobby.

This 143-room gem in the southern part of the Loop was one of many jewels in the crown of Chicago architect D.H. Burnham (who also designed Hotel Burnham). Built in 1897, it's a historic landmark known for its striking Arts and Crafts exterior and Frank Lloyd Wright–inspired decor. Rooms have high ceilings, huge windows, Prairie-style furniture, dual phone lines, and oversize bathrooms. Ask for a high-floor room to avoid noise from the El train along Wabash Avenue. Guests never go hungry here, thanks to free desserts (including the popular Eli's cheesecake) in the lobby and a deli that's open until midnight.

Parisian architect Jean-Paul Viguier designed the unique, Swiss cheese-like structure that houses the Sofitel. Just two blocks off the Magnificent Mile, this Gold Coast sophisticate hosts business travelers and Euro movers and shakers with its seductive lobby and 415 spacious rooms. Each has a marble bath and plenty of perks, including Web TV, two-line phones, high-speed Internet, and designer toiletries. The property's Café des Architectes serves excellent New French cuisine.

Restraint trumps gilt at this next-generation Trump project guided by Donald Jr., Ivanka, and Eric Trump. Spacious rooms—the smallest is 600 square feet—done in soothing gray and cream tones make you feel more resident than transient, aided by the condo-hotel's full kitchens with top-of-the-line Sub-Zero refrigerators, Wolf ovens, Miele cooktops, and Nespresso machines. Besting the high-style comforts are the views: The hotel occupies a prime riverside perch, taking in the Chicago River, Lake Michigan, and surrounding architectural jewels. Curved, east-facing, floor-to-ceiling windows look out on the Gothic Tribune Tower and the white terra-cotta-tiled Wrigley Building, the same view framed by the sixteenth-floor restaurant, Sixteen, where chef Frank Brunacci offers a ten-course "blind" tasting menu. The smartly dressed staff ensure that all guests are treated like VIPs—doors held, names used in greeting, DVDs not in the loaner library magically procured and waiting, with popcorn, in the room. Opened with just 50 rooms in January, en route to 339 when construction is complete later this year, the hotel is already drawing a status-conscious crowd splurging on $25-per-bottle Swarovski-crystal-encrusted Bling H2O, the top seller of the minibar's "water library."

The cool factor is high at this 235-room Loop head-turner from Starwood's hip W chain. Details from the former 1929 Beaux Arts gentleman's club can be seen in the lobby's vaulted arches and gold-leaf ceiling, although a 2009 renovation added thoroughly modern touches such as a carpet studded with LED lights to mimic the night sky. The stylish-but-small rooms were also redone with the hotel's twenty- and thirty-something clientele in mind—the mostly white design incorporates modular furniture, flat-screen TVs, and a magazine rack that converts to a cocktail bar. At night, a glam crowd fills the lobby, the Whiskey Blue bar (designed by Rande Gerber, Cindy Crawford's hubby), and the Tuscan-inspired Ristorante We. The scene at W's Lake Shore Drive location is even livelier, with a sizzling rooftop lounge (à la Gerber), the stylish Wave Restaurant, and the beach, bike paths, and Navy Pier just outside (644 N. Lake Shore Dr.; 312-943-9200).

This divine 11-room inn two blocks from McCormick Place is popular with conventioneers. Built in 1870 by Chicago Board of Trade president Calvin T. Wheeler, it's one of the few mansions to survive the Great Chicago Fire of 1871. In 1997, it was rescued from the wrecking ball, restored to its former glory, and proclaimed a national landmark. All 11 rooms feature high ceilings, 19th-century furnishings, antiques, armoires, and velvet drapes. Ask for a room with a tub (some only have shower stalls), or for one of the four with their own gas fireplaces. Hotel-style amenities include Egyptian-cotton sheets, towels, and robes, multi-line phones, and large desks with high-speed Internet.