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August 4, 2017updated Dec 20, 2023

Guide to Chicago

By Lauren Jade Hill

By Kristen Shirley

This story originally appeared in the July/August 2017 issue of Elite Traveler.

Chicago was once the “Second City” of the US, but these days it’s a world-class destination of its own. It has a wildly inventive culinary scene that made it the third US city to have its own Michelin Guide. There’s no shortage of classic experiences to be had, from shopping on the Magnificent Mile, to tooling around Lake Michigan on a yacht, indulging in world-famous deep-dish pizza or a Chicago-style hot dog, or catching a Cubs game at Wrigley Field. Above all, Chicago is a welcoming destination with famous Midwestern hospitality and a great mix of elegant experiences and family-friendly activities. And let’s face it, it’d have to offer a lot to make up for its notoriously brutal winters.

Top Restaurants


For its 10th anniversary last year, Chef Grant Achatz decided not to rest on his laurels—including his three Michelin stars—but to start a new, completely redesigning the space and the menu. Achatz continues to delight and surprise with his theatrical approach to cuisine. Now there are three dining spaces, including the new Kitchen Table, an exclusive and private experience for six.

Au Cheval

Consistently rated one of the best in the US, Au Cheval has scores of hungry locals and tourists wanting to try the famous burger here. Unless you are the president of the US, the governor of Illinois or the mayor of Chicago, don’t even try to get a reservation here. Take advantage of jet lag if you have it and arrive at 11am when they open, or put in your name and head to a nearby bar to wait for your table. Once your table is ready, you’ll find the diner-style burger with two beef patties, American cheese and a crispy bun is well worth the wait.


Chef Curtis Duffy’s acclaimed restaurant Grace earned three Michelin stars not long after opening (in Michelin years), which is quite an accomplishment for a young American chef. But considering his pedigree, it’s not too surprising. Before opening his own restaurant, Duffy honed his craft at Alinea, Avenues and Charlie Trotter’s. Here in his own refined space, Duffy offers two seasonal tasting menus, Flora or Fauna, that delight the senses and treat vegetables with the same precision and attention as meat. If staying at The Peninsula Chicago, arrange an exclusive tour and plate a dish alongside Chef Duffy courtesy of the hotel’s Keys to the City program.

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See Chicago…

By Land

No visit to Chicago would be complete without a selfie at Anish Kapoor’s iconic Cloud Gate sculpture, affectionately called the Bean, and a stroll through Millennium Park. If the weather is nice, take in a performance at the Frank Gehry-designed Jay Pritzker Pavilion and enjoy the outdoor art exhibits. Afterwards, head to the neighboring Art Institute of Chicago, home to over 300,000 works of art and world-class exhibitions, including the current Gauguin: Artist as Alchemist, on view through September 10.,

By Water

The Chicago River splits the city in two, giving it a true European feel. The best way to see some of its incredible architecture is right on the water. First Lady Cruises has partnered with the Chicago Architecture Foundation on a 90-minute tour led by a certified docent who points out incredible details and gives a sense of history. You can also book a private yacht for a more intimate experience.

By Air

There are helicopter tours, of course, but the two tallest buildings in the city compete for unique experiences. At the 108-story Willis Tower, step onto The Ledge, if you dare. Glass boxes extend out from the Skydeck and offer views from 1,353 feet above the city. For a less adrenaline-fueled experience, head to the Signature Lounge on the 96th floor of the John Hancock building, for a delicious brunch or cocktail with superlative city views.,

Design Hotels

Soho House

Even if you’re not a member, you can book a room at Soho House and enjoy its facilities including the famous rooftop pool, Cowshed spa and screening room. Located in the historic Allis building, the rooms are a mix of quirky and traditional decor, and the property has incorporated nods to its past throughout, including a marble mosaic in the lobby.

Chicago Athletic Association

One of the city’s buzziest recent openings, CAA embraces its name and heritage. From its landmarked 1890s Victorian gothic building to the vintage-inspired custom furnishings and boxing-style bathrobes, you’ll enjoy searching out all of the unique details of this charming hotel. Before an evening of rare spirits in the Milk Room or bocce, billiards and shuffleboard in the Games Room, be sure to enjoy sunset and the views of Millennium Park from the rooftop terrace, Cindy’s.

Take Three/// Top Suites

Presidential Suite
Four Seasons Hotel Chicago

High on the 46th floor, the Presidential Suite has a large living room, dining room for eight, private fitness room and full wet bar stocked to your personal preferences. The Pierre-Yves Rochon design is both classic and fresh, and makes the most of its sky-high views of the city skyline and Lake Michigan. Enjoy a complimentary spa treatment and a wet bar fully stocked to your tastes.

From $8,000 per night, Mariana Rietmann, guest services and relations manager, +1 312 649 2312,

The Peninsula Suite
The Peninsula Chicago
For a rare treat in the city, the Peninsula Suite has a 2,000 sq ft wraparound terrace with views of Lake Michigan that can be enjoyed from the many seating areas, or from your private Jacuzzi. The 3,645 sq ft suite can be booked with up to three rooms. The large living room has a gas fireplace and there is a separate formal dining room with seating for 10. Take in an afternoon of sightseeing courtesy of your chauffeured Mini Cooper.

From $9,000 per night,, +1 312 337 2888,

Infinity Suite
The Langham, Chicago

The two-bedroom, 2,700 sq ft suite is decorated in elegant neutral tones with luxurious white Statuario marble bathrooms. The grand living room has dining table for 10 with adjoining butler’s pantry, circular sitting area, desk, striking yellow grand piano and bar counter, surrounded by floor-to-ceiling windows showcasing stunning river views. Chuan Spa is one of the best in the city, and its Bathing Ritual is a can’t miss experience.

From $6,000 per night,, +1 312 923 9988,

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