Chicago Editor Picks

Editor Picks

Looking for the absolute best places to eat, sleep, shop, and socialize in the capital of jazz? Earning the discriminating vote of ShermansTravel.com editors, these picks comprise the city's can't-miss attractions, hotels, restaurants, bars, and shops – from the best way to appreciate the city’s architecture (a river cruise) to the best place to catch a set of live music (Green Mill).

Smart Splurge    Great Value
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.

2008 SMART LUXURY WINNER
Old-World Class

The Pen is that rare luxury hotel that is frequented by world travelers and locals alike. You’ll see couples on dates in the gold-domed lobby, sampling decadent desserts or catching a jazz performance, and local power brokers sipping finely crafted cocktails at the bar. The superior rooms are the largest anywhere in the city, and the hotel is parked in the center of the city’s prime shopping district. Best season for value: spring.

Great Value Alternative: City Suites has Art Deco rooms close to Wrigley Field and the best nightlife in the city. From $200/night; www.cityinns.com

See more Smart Luxury Award winners

 

108 E. Superior St.; Chicago, IL; 312-337-2888; www.chicago.peninsula.com
Tags: luxury | hotel | smart splurge | expensive | swimming pool | smart luxury winner
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.
140 E Walton Pl; Chicago, IL; 312-787-2200; www.thedrakehotel.com
Tags: luxury | hotel | historic | expensive
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.
333 N. Dearborn St.; Chicago, IL; 312-245-0333; www.hotelsaxchicago.com
Tags: hotel | moderate | trendy
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.
224 S Michigan Ave.; Chicago, IL; 312-922-3432; www.architecture.org
Tags: architecture | tour | things to do | history
This West Loop newbie has already been dubbed an instant classic. Think roasted rabbit with...more
123 N. Jefferson St.; Chicago, IL; 312-441-1920; www.sepiachicago.com
Tags: restaurant | expensive | notable chef | american
The Green Mill great value
Al Capone is among the legendary patrons to have climbed into one of the giant curvy booths at this legendary jazz joint and speakeasy.
4802 N. Broadway; Chicago, IL; 773-878-5552
Tags: jazz | historic | great value | nightlife | live music
Juicy Wine Co. great value
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.
694 N. Milwaukee Ave.; Chicago, IL; 312-492-6620; www.juicywine.com
Tags: trendy | great value | nightlife | lounge | wine bar
Armitage Avenue
Ancient Victorian homes tower over the haute boutiques, pricey gift shops, and high-end chocolatiers lining this bucolic avenue.
Armitage Ave.; Chicago, IL; www.armitageshopping.com
Tags: expensive | shopping | designer
Foodies are swooning over this candlelit wine bar and eatery. The simple and rustic menu is...more
1749 N. Damen; Chicago, IL; 773-486-2473; www.bluebirdchicago.com
Tags: romantic | moderate | trendy | restaurant | great value
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.
220 E. Chicago Ave.; Chicago, IL; 312-280-2660; www.mcachicago.org
Tags: culture | museum | things to do | art
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