Chicago

Overview

From Andrew Harper

Hunkered down at the southwestern edge of oceanic Lake Michigan, Illinois’ largest city (and the nation’s third-largest metropolis) has endured devastating fires, icy winds, Al Capone’s corruption and beleaguered baseball teams. Yet its hearty Midwestern character not only endures but flourishes, with dazzling architecture, gritty blues, innovative theater and comedy, rich cuisine and a welcoming heartland disposition.

Most visitors stay within the downtown “Loop” (the central business district circumscribed by the elevated metro tracks) and there are ample attractions here, from the nation’s tallest skyscraper, Sears Tower; to the art deco masterpiece, The Chicago Board of Trade Building; to the resplendent civic green space of Grant Park. The postmodern public art of Millennium Park and the world-renowned Art Institute of Chicago can constitute an afternoon alone. But for a truer taste of the city, venture out into the neighborhoods, like the North Side’s theaters, bars and clubs (and vintage baseball stadium, Wrigley Field) or the bohemian havens of the West Side, where, in Wicker Park, an independent arts scene thrives and Polish and Ukrainian cultural attractions offer a taste of the city’s Slavic roots. Enjoy a beer and sausage to bridge the Old World with the New.

Hotels

All recommended hotels in Chicago

Chicago, United States
Four Seasons Hotel Chicago
Four Seasons Hotel Chicago

Exceptional 345-room hotel offering impressive views from the 30th to 46th floors of a downtown tower complex incorporating upscale Michigan Avenue shops.

Illinois
The Peninsula Chicago
The Peninsula Chicago

Sophisticated 339-room hotel overlooking North Michigan Avenue in the heart of the premier shopping district.

Illinois
Trump International Hotel & Tower Chicago
Trump International Hotel & Tower Chicago

Contemporary 339-room hotel occupying the first 28 floors of a 92-floor steel-and-glass tower.

Illinois
Waldorf Astoria Chicago
Waldorf Astoria Chicago

Luxurious 188-room European-style hotel in prestigious Gold Coast neighborhood. Gated entry courtyard with central fountain.

Illinois

Dining

All recommended restaurants in Chicago

Everest

No one can argue about one attribute of this restaurant: The view is magnificent, as Everest is perched on the 40th floor of the Chicago Stock Exchange. The interior is low-key, with pale colors and discreet lighting. The food, however, will certainly grab your full attention. Chef Jean Joho hails from Alsace, and he combines that heritage with top American ingredients, as in a starter of crusted Berkshire pork cheeks with a choucroute salad. Among the main courses, you could find fillet of sole meunière with mousseline potatoes and petite capers, or rack of lamb with slow-cooked fava beans, fingerling potatoes and mint pistou. The wine list contains more than 1,600 selections. Closed Sundays and Mondays.

440 South LaSalle Street 40th Floor
Chicago, IL 60605
United States
$95
Grace

This stylish restaurant comes with leather chairs, fine linens and soft lighting. Chef Curtis Duffy previously worked at Charlie Trotter’s and The Peninsula’s Avenues, where he earned two Michelin stars. Each night, he creates two prix-fixe menus, one vegetarian. Look for dishes such as asparagus with brioche, lemon and tarragon; cod with osetra caviar, lychees and chives; lamb with artichokes, smoked paprika and frisée; and Miyazaki beef with romaine, peanuts and Vietnamese herbs. Partner/sommelier Michael Muser’s fascinating wine list emphasizes the Loire and the Rhône. Closed Sundays and Mondays.

652 West Randolph Street
Chicago, IL 60661
United States
$205
Les Nomades

This is one of the prettiest restaurants in the city, set in a turn-of-the-century brownstone. The menu is contemporary French. Look for the rich assortment of house-made pâtés served with cornichons and toasted brioche. Main courses might include Arctic char with maitake mushrooms, forbidden rice and tapenade in a yellow tomato-lemongrass sauce; or braised beef short rib with root vegetables and trumpet royale mushrooms in a shallot sauce. The extensive wine list has 17 selections by the glass. Closed Sundays.

222 East Ontario Street
Chicago, IL 60611
United States
Four-course menu, $115; five courses, $130
MK

Mellow brick walls, soaring windows and a vaulted wood ceiling create a handsome setting for the impeccably prepared food of chef Michael Kornick. A starter of two tartares comprises yellowfin tuna tartare with a celery root remoulade, and salmon tartare with a citrus crème fraîche and salmon pearls. Among the main courses, you could find salmon grilled over hardwood charcoal and served with bok choy glazed with Chinese mustard, or a similarly grilled prime New York sirloin with roasted fingerling potatoes, baby leeks and a red wine sauce.

868 North Franklin Street
Chicago, IL 60610
United States
$70. Six-course tasting menu, $90
North Pond

This 1912 structure once served as a warming shelter for ice skaters. The redone interior is a fine example of the Arts and Crafts style, with wood accents, ochre brick walls, period posters and a feel of rustic elegance. Chef Bruce Sherman’s creative menu is keyed to seasonal ingredients. Recent starters included a butter-basted sturgeon with horseradish-lemon new potatoes, onions, almonds, a mint purée and lovage. Look for main courses such as steamed turbot with shrimp mousseline, fennel jam, orange and smoked caviar; or browned lamb chop with fennel-spiced lamb shoulder, grilled romaine lettuce, golden raisin purée and cauliflower. The wine list has 14 selections by the glass. Closed Mondays and Tuesdays.

2610 North Cannon Drive
Chicago, IL 60614
United States
$65
Spiaggia

The city’s finest Italian restaurant overlooks Oak Street Beach and showcases the talents of chef Tony Mantuano. The main dining room has been redesigned for its 30th anniversary. The seasonal menu changes, but look for pastas such as ravioli with foie gras, hazelnuts, rhubarb and 18-year-old balsamic vinegar; or potato gnocchi with ricotta sauce and black truffles. Main courses might include Atlantic hake with Petrossian caviar, oyster cream and onion confit; or a free-range veal chop with asparagus, wax beans and baby arugula.

980 North Michigan Avenue
Chicago, IL 60611
United States
$95. Six-course tasting menu, $165
Takashi

Chef Takashi Yagihashi serves food billed as French-American with Japanese influences. The spare space has burnished wood tables, charcoal-gray walls, shoji screens and a strategically placed bonsai. Among the intriguing choices: sautéed Maine scallops and soba gnocchi with trumpet royale mushrooms in a celery root-Parmesan foam; Amish chicken in a clay pot with shimeji mushrooms, eggplant and haricots verts, with tangy yuzu juice; and pork loin two ways — seared with ginger and soy and as a cutlet with Brie and pancetta. The wine list is based on the predominant characteristics of the wines, so you will see categories such as “Crisp, Clean and Refreshing” for whites and “Big Boys” for reds. Closed Mondays.

1952 North Damen Avenue
Chicago, IL 60647
United States
$65