Downtown Chicago at night
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Chicago City Guide

Chicago Travel Guide

Rising up from the southwestern edge of oceanic Lake Michigan, Illinois’ largest city (and the nation’s third-largest metropolis) has endured devastating fires, Al Capone’s corruption and beleaguered baseball teams. Yet its hearty Midwestern ...

Rising up from the southwestern edge of oceanic Lake Michigan, Illinois’ largest city (and the nation’s third-largest metropolis) has endured devastating fires, Al Capone’s corruption and beleaguered baseball teams. Yet its hearty Midwestern character not only endures but flourishes, with dazzling architecture, gritty blues, innovative live theater and comedy, world-class restaurants and a welcoming heartland disposition. 

Most visitors stay in or near 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, Willis Tower (formerly known as the Sears Tower); to the Beaux-Arts Chicago Cultural Center, boasting elaborate mosaics and the world's largest Tiffany glass dome; to the resplendent civic green spaces of Grant and Millennium Park. The justly renowned Art Institute of Chicago can constitute an afternoon alone. And in warm weather, there is no better introduction to the city than a fascinating architectural boat tour along the river (the Chicago Architecture Foundation has the best).

But to really get to know Chicago, venture out into the neighborhoods, exploring the North Side’s theaters, bars and clubs (and its 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 businesses and cultural attractions offer a taste of the city’s Slavic roots. A remarkable string of parks, beaches and marinas borders the entire eastern side of the city and Lake Michigan.

Recommended Luxury Hotels in Chicago

All Andrew Harper-recommended hotels offer impeccable accommodations and high levels of personal service. Only the best of the best make our list, so we rate them on a scale from bird icon 90 to 100.

Best Restaurants in Chicago

This stylish and expensive restaurant comes with leather chairs, fine linens and soft lighting. Chef Curtis Duffy previously worked at Charlie Trotter’s and The Peninsula’s Avenues, and he now helms one of Chicago’s two Michelin three-star restaurants. Each night, he creates two prix-fixe menus, one vegetarian. Look for dishes such as English peas with huckleberry, sea beans and yarrow leaves; bigeye tuna with caviar, coconut and miner’s lettuce; and short rib with watercress, lime and Vietnamese herbs. Partner/sommelier Michael Muser’s fascinating wine list emphasizes the Loire and the Rhône. Closed Sunday and Monday.

652 West Randolph Street Chicago $300

The city’s finest Italian restaurant overlooks Oak Street Beach and showcases the talents of chef Tony Mantuano. The seasonal menu changes but includes exquisite pastas such as spaghetti with fonduta, peas, ramps and beech mushrooms; or potato gnocchi with ricotta sauce and black truffles. Main courses might include salmon with red cabbage and pea tendrils; or duck with foie gras, green walnuts, carrots and speck. 

980 North Michigan Avenue Chicago $130. Six-course tasting menu, $125

The view here, from the 40th floor of the Chicago Stock Exchange, is magnificent. 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 Wisconsin veal with wild Michigan morels and spring peas à la Française. The wine list contains more than 1,600 selections. Closed Sunday and Monday.

440 South LaSalle Street Chicago $110

Celebrity chef Rick Bayless’ newest venture is already a tough reservation. The kitchen cooks everything over a woodburning grill, and the Baja-inspired menu offers strikingly complex flavors. One appetizer combined the sweet and charred flavor of roasted pineapple with creamy goat cheese, tangy orange-lime broth and spicy hazelnut salsa macha. I also loved our main courses, such as black cod with savory “pastor” marinade and sweet pineapple-shiso salsa. Bayless’ engaging daughter, Lanie, arranged for a superb selection of mezcals to pair. Closed Monday.

900 West Randolph Street Chicago $70

Chicago has no shortage of fine steakhouses, but the candlelit atmosphere of Bavette’s makes it more appropriate for couples than for businessmen. We had a wonderful dinner of cognac-infused foie gras with a blackberry compote, garlicky shrimp de Jonghe, tender lamb T-bone with rosemary and garlic, and flawless filet mignon with roasted tomatoes and spicy watercress. Our side dishes of creamy elote-inspired corn and flavorful roasted butternut squash with sage proved equally delicious. 

218 West Kinzie Street Chicago $95

This tiny BYOB restaurant hidden in an unpromising northside neighborhood is no longer a secret, since its acquisition of two Michelin stars. Tickets purchased through the website include the tasting menu, tax and tip, as well as seats at either a 10-person communal table or a counter facing the open kitchen (our preference). A wildly creative dish of asparagus gelato, salt-cured tuna, sea buckthorn cream, wood sorrel and apricot kernels created fireworks of flavor, as did courses such as triple-seared Miyazaki wagyu beef with baby bok choy, Japanese pickled plums and rich crumbs of dehydrated beef marrow. Well worth the taxi ride. Closed Monday and Tuesday.

4662 North Broadway Chicago Ticket: $260

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 Alaskan halibut with quinoa, saffron potato cakes and morel mushroom sauce; or braised wagyu beef short rib with root vegetables and trumpet royale mushrooms in a Bordelaise sauce. The extensive wine list has 17 selections by the glass. Closed Sunday and Monday.

222 East Ontario Street Chicago Four-course menu, $125; six courses, $140

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