Chicago: Editor Picks

Architectural River Cruise The city’s “living museum” of architectural treasures are candidly and humorously uncovered during these lively docent-led tours down the Chicago River. The Loop; 224 S Michigan Ave.; 312-922-3432; www.architecture.org
architecture | tour | things to do | history

Armitage Avenue Ancient Victorian homes tower over the haute boutiques, pricey gift shops, and high-end chocolatiers lining this bucolic avenue. Lincoln Park; Armitage Ave.; www.armitageshopping.com
expensive | shopping | designer

Bluebird Foodies are swooning over this candlelit wine bar and eatery. The simple and rustic menu is heavy on sharing (think flatbreads with serrano ham and marchego cheese or a simple braised rabbit over fettuccini) while the extensive wine list boasts nearly two-dozen wines by the glass, each for less than 10 bucks. Bucktown; 1749 N. Damen; 773-486-2473; www.bluebirdchicago.com
romantic | moderate | trendy | restaurant | great value

Hotel Sax Out of the ashes of the old House of Blues Hotel, a thrilling new Phoenix, the 357-room Hotel Sax, has risen. Old World meets new in a tasteful setting that artfully mixes vintage glamour and urban style. Studio rooms are European in feel and drenched in dark wood paneling, while deluxe kings revel in over-the-top amenities like 42” flat-screen TVs. If the “Microsoft Lounge” gaming room, featuring five Zune MP3 players, five Xbox 360 Elite game stations, and a Windows home entertainment PC, doesn’t entertain you, then nearby Crimson Lounge, 10 Pin Bowling Alley, or the ubiquitous House of Blues surely will. River North; 333 N. Dearborn St.; 312-245-0333; www.hotelsaxchicago.com
hotel | moderate | trendy

Juicy Wine Co. Hipster oenophile Rodney Alex has struck gold in the form of this understated gem where local scenesters come for gobs of yummy cheese and an unbelievable wine selection. River West; 694 N. Milwaukee Ave.; 312-492-6620; www.juicywine.com
trendy | great value | nightlife | lounge | wine bar

Museum of Contemporary Art Everybody admires the MCA’s serious commitment to cutting-edge art – including works by the likes of Lee Bontecou, Dan Flavin, and Jasper Johns. But just try and stop the hipsters from schmoozing and boozing at the insanely popular First Fridays, or working up a sweat while winning fabulous prizes during Bingo/Tango on the second Tuesday of the month. Magnificent Mile/Streeterville; 220 E. Chicago Ave.; 312-280-2660; www.mcachicago.org
culture | museum | things to do | art

Sepia This West Loop newbie has already been dubbed an instant classic. Think roasted rabbit with ricotta dumplings or slow baked veal breast with mint noodles in a setting that marries Art Nouveau with simple modern. West Loop; 123 N. Jefferson St.; 312-441-1920; www.sepiachicago.com
restaurant | expensive | notable chef | american

The Drake The famous lakefront property is marvelously elegant, with a magnificent setting that never fails to attract a slew of royalty and celebrities alike. The hotel recalls the heyday of a regal eras past with a grand design and a trove of prestigious accolades. The beach is just a stroll away, as well as Magnificent Mile, with its designer stores, eateries, and attractions galore. The Drake’s 537 spacious rooms have all been updated with upscale, modern amenities, but still retain their traditional antique-filled decor and large windows framed by heavy, fringed curtains. All the rooms come with executive desks, on-demand movies, in-room safes, and high-speed Internet access; many have sitting areas and boast gorgeous city views and lake views (more expensive). Executive rooms and suites offer additional amenities such as daily continental breakfast in a private lounge (where you can also imbibe free cocktails in the evening); daily newspaper delivery; shoe-polishing valet; packing and unpacking service; and dinner, theater (and other) ticket concierge. Magnificent Mile; 140 E Walton Pl; 312-787-2200; www.thedrakehotel.com
luxury | hotel | historic | expensive

The Green Mill Al Capone is among the legendary patrons to have climbed into one of the giant curvy booths at this legendary jazz joint and speakeasy. Uptown; 4802 N. Broadway; 773-878-5552
jazz | historic | great value | nightlife | live music

The Peninsula This extravagant hotel’s wow factor is undeniable. The lobby features soaring white-marble walls that lead to a gold-domed lounge infused by the sounds of live music, courtesy of a small orchestra or band perched atop the balcony. The hotel’s numerous accolades have noted its smart blend of contemporary and classic styles; its state-of-the-art electronic system (which allows guests to control the temperature, lights, and even the curtains from the comfort of their own bed); its posh spa (also one of the country’s best); and its terrific dining establishments – including seafood, Asian, and a European bakery – which offer unrivaled sophistication and superb cuisine. The hotel’s 339 luxurious guest rooms are some the largest in Chicago and are decked out in a chic, classical style suffused in soothing colors and soft linens. Most rooms offer stupendous city views, a comfortable sitting area with an overstuffed sofa and coffee table, and over-the-shoulder lighting for bedtime reading. All units have marble bathrooms that come with a separate shower and tub, a hands-free phone, TV, and mist-free mirrors. Magnificent Mile; 108 E. Superior St.; 312-337-2888; www.chicago.peninsula.com
luxury | hotel | smart splurge | pool | expensive | smart luxury winner