Amble among the affluent in the Gold Coast.
Chicago Tour: Gold Coast
Credit: Tetra Images / Alamy

Prominent Chicago businessman Potter Palmer built Palmer Mansion on Lake Shore after the Great Chicago Fire of 1871, establishing the opulent standard of the Gold Coast neighborhood. Today, the Gold Coast still epitomizes wealth and prestige. Encompassing the north end of the Magnificent Mile, the neighborhood is home to some of Chicago’s most elite shops, world-class hotels, posh restaurants, and unparalleled architecture. The atmosphere here speaks of tradition and grandeur. Walk on State Parkway between Banks and Schiller to see the old Playboy mansion. Stroll down Astor Street District to see stunning Victorian architecture. Don’t miss the quaint, historic firehouse on Chicago between Michigan and Lake Shore. Find designer boutiques on Oak Street. Head to Rush and Division for classy cocktails. And take time to visit Oak Street Beach, which offers a unique beach experience: sunbathing while gazing at the Chicago skyline.

The Signature Lounge

Instead of visiting the John Hancock Center’s zenith during daylight hours, opt for an evening cocktail in the building’s high-flying lounge. Located on the 96th floor, the dimly lit bar has dazzling 360-degree views of the city. With three salons to choose from, you can romance a date at a window table in the south lounge or socialize with a group on the west lounge’s long leather couches. (The north lounge is closed during winter.)

Museum of Contemporary Art, Chicago

Add some color to an afternoon in Chicago with a visit to the Museum of Contemporary Art, one of the largest contemporary art museums in the country. Designed by architect Josef Paul Kleihues, the five-story building has three floors of dedicated gallery space extending from a central glass atrium. Highlighting pieces from 1945 to the present, the permanent collection focuses on surrealism, minimalism, conceptual photography, and work by Chicago-based artists. Pieces include those by Jeff Koons, Andy Warhol, Jasper Johns, and Alexander Calder. Exhibits change monthly, and free docent-led tours provide insight into select works.

Bistro Zinc

The bread and butter alone are worth the trip to this quaint French bistro with Provençal-yellow walls, tin ceiling, and zinc-top bar. While its cocktails are made with spirits from a local distillery, its menu is straight from France: Don’t miss classic dishes like steak frites, croque monsier, and housemade pâté, as well as its decadent desserts.

900 North Michigan Shops

The ultimate shopping experience, 900 North Michigan boasts six floors of more than 70 luxury retailers, comprised of both national brands and boutiques, including Gucci, Michael Kors, and Bloomingdale’s. Spend the day shopping and enjoy a respite at one of the several cafés and eateries in this label-lovers’ paradise.

Allium at the Four Seasons Hotel

Located in the Four Seasons Hotel, Michelin-starred Allium’s chefs source ingredients from local farmers to create seasonal farm-to-table American fare, including favorites like bison tartare, country rabbit sausage, and double-cut lamp chops.

Chocolate at The Pen

On Friday and Saturday nights, indulge in the decadent Chocolate Bar at The Lobby on the fifth floor of The Peninsula Chicago. Sip a chocolate martini and nibble on chocolate truffles, chocolate cake feuilletine, chocolate-dipped strawberries, and other cocoa treats in an elegant setting swathed in muted colors.

Newberry Library

A distinguished independent research institution with over 1.5 million books, the stately Newberry Library holds free exhibitions and lectures, all open to the public. Whether or not you’re in the mood to crack some spines, the magnificence of the building itself is worth the visit. Catch a free tour of the library on Thursday afternoons or Saturday mornings.