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The Fairmont Chicago
200 N. Columbus Dr. (E. Lake St.)
Chicago, IL 60601
312-565-8000, 800-527-472

Long on amenities, this hotel features 692 sizeable, good-looking rooms and posh public spaces. The neo-Classical building is covered in rosy, Spanish granite, and the works of Chicago-area artists are proudly displayed in the lobby—atypical hotel art pieces that will please discerning guests. In the well-appointed rooms, marble baths come with TVs, separate shower stalls and WCs with doors (very civilized). Also nice are the triple-sheeted beds, down pillows and shoe polishers in each room. While the hotel doesn't have its own health club, it's connected to one of the largest in the city:  At the Athletic Club Illinois Center, you can even rope your way up a faux mountainside. The same golf facility used by the nearby Swissôtel also serves this property's clientele. Two well-respected restaurants include the elegant and romantic The Aria Restaurant & Barn and the informal Garden Courtyard.

Hotel Sax Chicago
333 N. Dearborn St. (W. Kinzie St.)
Chicago, IL 60611
888-407-4856

This hip hotel was designed to be decidedly different. The lobby is draped with flowing tapestries and Eastern artifacts, and you're handed a CD case welcome kit at check-in. Loudly patterned hallways lead to the loudly patterned (but fun) guest rooms and suites, where meditation messages are offered with turndown service. The 367 rooms include smaller but still funky cabins, and some of the 22 suites boast soaring city views. Amenities include 42" flat screen TVs, 320-thread count linens, in-room faxes, CD players, VCRs, voice mail, dual-line phones and wireless Internet access. Twenty-four-hour room service, a pet-friendly policy and a "did-you-forget" closet filled with all kinds of necessities are additional perks. The hotel complex houses a Crunch Fitness Center and a 36-lane bowling alley.

Walking the line between a boutique and luxury hotel, this swank establishment is the first in a line of modern, aesthetically pleasing properties courtesy of Danny Errico, one-time CEO and founder of the Equinox Fitness Clubs, and Brad Wilson, former V.P. of Operations and a founding member of W Hotels. Located just off of the Mag Mile, it's near the John Hancock Building, McCormick Place, Millennium Park, Navy Pier, River North and the Water Tower Place. The rooms are minimalist-chic with rich wood platform beds, private dining niches, plasma screen TVs and spacious slate and marble bath facilities. Other perks include an in-room stereo with iPod dock, Etienne Aigner bath amenities and complimentary wireless Internet access. Dining at the hotel doesn't disappoint with David Burke's modern Primehouse in residence. And the hotel's lounge, J Bar, is a great spot to discuss business over "deconstructed" cocktails and delish tidbits like crab meat truffles with poppy seed honey.

The Palmer House Hilton
17 E. Monroe St. (N. State St.)
Chicago, IL 60603
312-726-7500

This recently restored hotel was originally opened in 1871, just thirteen days before the Great Chicago Fire reduced it to ashes. Chicago real estate baron Potter Palmer immediately built a new hotel on the site—at three times the size of the original and ten times the cost. It was the first Chicago hotel to have fireproofing, elevators, electricity and telephones and was the home-away-from-home of such colorful figures as Mark Twain, Charles Dickens and Oscar Wilde. Now, standard guestrooms sport rich shades of green and black, while lavender, chocolate, gold, blush and powder blue hues appear throughout the suites. In both cases, artwork is informed by the property's locale, so Chicago's rich history is reflected in photography from the 1893 World's Fair and Chicago's contemporary local artists lend modern appeal.Rooms feature modern amenities like high-speed Internet access and large work desks. For added convenience, book an executive room, which comes with a morning newspaper, continental breakfast and access to a private elevator. While you're here, be sure to check out the hotel's newly opened crown jewel: Lockwood, a French and Italian-influenced, upscale American spot on the lobby level.

Trump International Hotel & Tower Chicago
401 N. Wabash Ave.
Chicago, IL 60611
312-588-8000, 877-458-7867

Located in the heart of the city, this Skidmore, Owings & Merrill-designed luxury hotel with sweeping city views welcomed its first hotel guests in January 2008. Located on floors 14-27 of a 92-story residential tower in development by the Trump Organization, its 339 luxuriously appointed, contemporary guestrooms and one-, two- and three-bedroom suites with modern, fully appointed kitchen, ten-foot floor-to-ceiling windows, a sitting area with a sofa bed, WiFi, 42-inch LCD TV and luxury bathrooms outfitted with Kohler deep soaking tubs, separate shower and in-mirror TV portal. Also on site is Sixteen, a fine dining restaurant featuring modern American cuisine, as well as top-tier meeting and event space and a chic lounge that's perfect for sealing deals. Attaché services—including a customized fully stocked refrigerator and complimentary personalized stationary, on request—are among the hotel's perks.

Gibsons Steakhouse & Bar
1028 N. Rush St. (E. Bellevue Pl.)
Chicago, IL 60611
312-266-8999

The upscale chains hitting town lately have nothing on this home-grown steakhouse. The bar and hallway are packed nightly with beefy businessmen in dark suits, young Turks in stone-washed jeans, lovelies in little black dresses, sports figures, politicos and average Joes and Janes waiting for tables in the clubby, wood-paneled dining room. Prime aged steaks—displayed raw tableside along with giant lobster tails—are the main draw, but chops and fish also rank high. Everything is on a gargantuan scale, from the martinis to cakes that easily feed four. Fortunately, affable servers encourage the sharing of entrées.

Sepia
123 N. Jefferson St. (Randolph St.)
Chicago, IL 60661
312-441-1920

How many times have we heard about the importance of first impressions? One look around the chic, well-thought-out décor of Sepia—custom millwork, modern chandeliers, a floor-to-ceiling wine wall—and it's obvious owner Emmanuel Nony was listening. But more than just a pretty face, this Fulton Market District restaurant has the food to back it up. Chef Kendal Duque (Everest, TRU) works with seasonal, top-quality ingredients and then stands back and lets their flavors shine. The watermelon and shaved fennel salad with goat-milk yogurt dressing is bright and vibrant, while the sirloin steak tartare with a raw farm egg is comfort food with a college degree. We also recommend the veal breast entrée with mint noodles and cipollini onions. Desserts—fresh fruit bread pudding, chocolate soufflé—have the same rustic-yet-refined appeal as the rest of the menu. Even cocktails feel the love, with ice cubes specially designed for a slower melt. The selection of international and domestic wines focuses on small artisanal producers who follow organic, sustainable and biodynamic winemaking practices. Service is skilled and knowledgeable.

Tru
676 N. St. Clair St. (Huron St.)
Chicago, IL 60611
312-202-0001

Tru's "progressive French" cuisine is immaculate in its conception, precise in its presentation and perfectly realized in taste and flavor. We love the black truffle risotto with fava beans and lobster, but the lemongrass steamed Icelandic salmon makes us pause to savor the goodness after each luscious bite. There are several dinner options, including a three-course prix fixe menu and a nine -course "chef's market collection," and a seven-course "seasonal collection." The setting is as smart as the cuisine. Crisp, white cloths cover tables spaced for privacy, and minimalist, chic decor is as cool as the patrons who are eating this place up with a spoon.

Bin 36
Hotel Sax
House of Blues Hotel
339 N. Dearborn St. (Kinzie St.)
Chicago, IL 60611
312-755-9463
www.bin36.com

Industrial-chic Bin 36 includes a wine shop, coffee bar, cheese bar, a zinc-topped wine bar, a café, a dining room (called the Cellar) and function rooms. As the name implies, wine is the focus, and there are two wine lists. One features 50 vinos available by the taste, glass or bottle—as well as in flights. The other showcases more than 200 bottles. Much is done to demystify wine and to help the diner pair wines with food, to the point of distraction on occasion. At breakfast and lunch, the casual café (with a bistro menu of burgers, pizzas, salads, rotisserie chicken) is the center of activity. During dinner, the more formal (white tablecloth) dining room tends to fill up, too. Here, the lineup is fairly upscale—seafood, rib-eye steak, pork chops—but anyone can order from either menu in either room. If you want something light, consider having one or more of the imported and domestic cheeses with wine. The retail part of the space sells wines and related paraphernalia. A full-fledged cheese bar lets patrons sidle up to select from 50 kinds of well-traveled cheeses.

The Gage
24 S. Michigan Ave. (Monroe Ave.)
Chicago, IL 60603
312-372-4243
www.thegagechicago.com

You can call The Gage many things—a pub, a gourmet dining experience, an after-work hangout, a swanky wine bar—but don't call it a gastropub. At least not to owner Billy Lawless, a native of County Galway, Ireland, who feels the term is often misunderstood in the States. Perhaps The Gage's spot-on combination of creative-yet-recognizable dishes designed by talented chef Dirk Flanigan (Meritage, Blue Water Grill) paired with an impressive bar menu, including interesting wines, craft beers and a large selection of Irish whiskeys and single malts and a chic-yet-cozy atmosphere can clarify things. Located in an historic building across from Millennium Park—the communal table by the front window offers the best view. This tavern has a menu that offers a variety of dining options. Create a meal from the appetizer list—the fried chicken livers, braised rabbit salad and beef carpaccio with roasted mushrooms are all good ways to start. Or choose one of the hearty entrées, including roasted Amish chicken, roast saddle of elk or Guinness-battered fish 'n' chips. The house burger made with ground Angus beef topped with local Camembert and onion marmalade is a standout.

House of Blues
329 N. Dearborn St. (Kinzie St.)
Chicago, IL 60611
312-527-2583
www.hob.com

A thumping trilogy of food, entertainment and blues makes this one of downtown Chicago's hottest places, especially after a hard day of wheeling and dealing. Go for the food—catfish bites, crawfish cheesecake, ribs, jambalaya and the like—and stay for the music. Not your cup of gumbo? Snag mac 'n' cheese baked in a cast iron skillet, a blackened chicken sandwich with chile-garlic mayo or the pan-seared voodoo shrimp served with rosemary cornbread and Dixie beer reduction. Gospel Sunday brunch is always a sell-out.

Millennium Park
Columbus Dr. and Randolph St.
877-244-8846
www.millenniumpark.org

A series of redevelopment projects are infusing downtown Chicago with a little of the architectural spirit the city is known for. Finally opened in 2004, Millennium Park extends the reach of Grant Park and adds 21st century pizazz. Two 50-foot glass towers display changing video images and spout water in the park's dramatic Jaume Plensa-designed fountain. Wander through the Lurie Garden with its more than 200 species of flowers, go ice skating or hear the Grant Park Orchestra perform at the futuristic Jay Pritzker Pavilion. Designed by Frank Gehry, the 4,000 seat amphitheater epitomizes the soaring stainless steel creations he's known for. Think Guggenheim Bilbao or the Disney Concert Hall.

Touting itself as the city's first "liquor spa," this Zen-looking, wee-hours lounge—whose menu comes from almost-"Top Chef" Dale Levitski (Trio Atelier, La Tache, Orange)—is a class act. Sporting an all-out natural feel (think bamboo, metal and stone details, not to mention a trickling waterfall), it's the kind of place where you need to plan ahead to reserve tables for VIP treatment. Taking bottle service to another level, patrons order their liquor of choice, and it comes with an array of house-made mixers (think huckleberry-mint soda), garnishes (toasted cinnamon sticks) and "assiettes" (Walla Walla-chèvre tart) A full bar promises regular folks plenty of luxury, too, in the form of a Caprese cocktail (with pepper vodka, tomato, basil and mozzarella). Sustenance for mortals includes horseradish-accented prawns, tempura fruit with coconut and orchids and fingerling potatoes with cabrales. The spot sports upholstered seating and a designated, heated outdoor area where patrons can sneak puffs since smoking is now illegal in public places.