This hipster hotel in River North is filled with quirky design touches (red lips on the bathroom mirror; mannequin trapeze artists suspended in the courtyard).
The tall glass-and-steel structure cuts a commanding figure against the Chicago skyline. High-tech rooms come with iHome docking stations and RFID key cards.
A Mad Men–meets–The Brady Bunch–style lobby, with tweed upholstered furniture and bow-tied bellhops, welcomes you to this refurbished 1928 property opposite the park.
In a landmark Mies van der Rohe building, the Langham is awash in mid-20th-century grandeur, from the Dirk Lohan–designed lobby to the Bauhaus artwork by Judy Ledgerwood and Anish Kapoor.
Ian Schrager’s Chicago hotel remains a local favorite: the revamped Pump Room restaurant is one of the hottest tables in town.
Industrial-chic interiors, the work of British designer Tara Bernerd, are done up in concrete, brick, and wood; guest rooms have turquoise velvet sofas and black marble-topped tables.
Everything here is over the top: the 23,000-square-foot spa, 24-chair salon owned by celebrity stylist Anthony Cristiano, and personal attaché service (which includes access to a Cadillac).
Occupying 18 floors in a 67-story high-rise overlooking Chicago Avenue, Park Hyatt has a covetable central location. Rooms incorporate reproduction Eames furniture and oversize soaking tubs.
At this stately property, the concierge greets you by name; classical music plays when you enter your room; and your bedside table has a control panel to alert housekeeping when you want service.
Israeli retailer Ikram Goldman's 16,000-square-foot fashion emporium in the Gold Coast carries daring statement pieces (Viktor & Rolf ruffled black leather jackets; flirty Lanvin dresses).
Best bets at this Midcentury Modern furniture and housewares store in historic Thalia Hall: cutting boards by locally based Solo Home Design, created from reclaimed wood and recycled bike parts.
For Chicago’s finest selection of antiques, head to this beautifully edited shop in Andersonville. On any given day you might find a bespoke Edward Fields rug or a lamp by designer Ted Harris.
The racks at this young entrepreneur’s Gold Coast boutique are filled with lesser-known American designers such as Nicholas K and Timo Weiland. Look out for her signature candle collection.
The Renzo Piano–designed Modern Wing at the renowned museum showcases contemporary art and design. The original Beaux-Arts building has a great collection of Post-Impressionist paintings.
Come here for forward-thinking installations by emerging and established talents, and the city’s only video art space. Highlights include Spanish artist Casilda Sánchez and Tel Aviv–born Einat Amir.
The best way to learn about the city’s historic buildings (the Tribune Tower; Merchandise Mart) is on a boat tour run by Chicago Architecture Foundation guides.
The 54-year-old sketch comedy club has been turning out A-list stars—Tina Fey; Steve Carell; Stephen Colbert—for more than 50 years, and is still the place to catch fledgling writers and actors.
Many of the silver screen’s preeminent names (John Malkovich; Joan Allen) have performed at this legendary theater, with three venues for plays, musicals, and other events.
The 20-course menu at all-white dining room in Lincoln Square is divided into three sections (farm; woodlands; ponds, lakes, and seas), with crowd-pleasers like lamb loin wrapped in dandelion greens.
Fat Rice has gained a cult following for its innovative Macanese dishes. Those who brave the hours-long wait are rewarded with shareable plates that take cues from India, Southeast Asia, and Portugal.
In an industrial space with burnt-cedar walls, Top Chef winner Stephanie Izard turns out nose-to-tail specialties, including fried pig face and kidneys stuffed with goat confit.
Nearby Girl & the Goat (its sister branch), Izard puts a creative spin on classic breakfast dishes; try the sourdough pancakes.
Chicago’s hipster tribe pack this locavore temple in Logan Square for Saturday brunch. Start cheesewurst at the pop-up sausage stand on the patio, then head inside for waffles with pork belly.
You need to buy a ticket on the website to get a table at chef Grant Achatz’s follow-up to foodie hot spot Alinea—and they go quickly. But if you manage to snag one, you’re in for a treat.
A 1977 El Camino marks the entrance to this no-frills spot in Logan Square. Young chef Hunter Moore serves cobia ceviche accompanied by craft beers and negroni slushes.
For the city’s best oysters and aged charcuterie, head to Paul Kahan’s buzzy restaurant, the Publican. Across the street, his just-opened butcher shop serves a killer barbecued veal brisket sandwich.
Behind a nondescript door in Wicker Park, Violet Hour serves handcrafted drinks (try the Hush & Wonder, made of Matusalem rum, lime, and crème de violette).
Ward Eight, in Evanston, is a saloon-style bar with well-worn church pews; get the Hemingway.
Anything goes at this music venue in Bucktown—from Baudelaire-inspired shows to performances by indie rock bands.
This joint serves delicious small plates (try the crisp lamb ‘scrumpets’) and craft cocktails.
No one should leave Chicago without a ride on the El train around the Loop—it’s the best way to see the city.
Come here for a wide selection of coffee-table books, clothing from emerging designers, and cool housewares.
A state-of-the-art theater that screens independent, international, and classic films.
A funky new coffee shop in East Lakeview complete with sleds, canoes, and an incredible speaker installation built out of vintage suitcases.
The trek to the Far North Side is worth it for Katsu, often touted as the city’s most authentic sushi restaurant.
Many people think Midwestern cuisine is all about meat and potatoes, but GT Fish & Oyster proves them wrong. The seafood dishes are excellent (don’t miss the bacon clam chowder).
This café serves some of the best coffee in town, thanks to its personal touch and unbeatable brews.
Exploring the shoreline of Lake Michigan is a must—it’s what makes Chicago unique.
