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Checking Into the Hilton Chicago

Tour the windy city in style while staying at the AAA Four Diamond Rated Hilton Chicago, right across the street from Lake Michigan. 

hilton chicago

The Hilton Chicago.

(Photo: AAA.com/Hotels)

If you’re heading to Chicago and want to be in the middle of everything, book a stay at the AAA Four Diamond Rated Hilton Chicago. This classic Windy City hotel is ideally situated on Michigan Avenue and takes up an entire city block between Seventh and Eighth streets, plus, it’s across the street from Grant Park and Lake Michigan. I was fascinated to learn more about this historic Beaux-Arts property, which recently unveiled a $150 million renovation. Here’s an overview of my experience and what you can expect while at the Hilton Chicago.

History of the Hilton Chicago

The structure opened in 1927 as the Stevens Hotel with 3,000 rooms. It was one of the largest and most opulent hotels in the world, with a grand two-story entrance hall with twin staircases, marble columns and fresco-style gilded ceilings. It also had a bowling alley and an ice skating rink! When the Depression hit, the hotel fell on hard times and during WWII it was used as military barracks. Eventually, it was bought by Conrad Hilton who brought it back to its former prominence. Today, the lobby is still grand, with its famous clock tower where people make plans to meet (I loved the people-watching in this elegant, bustling space).

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The Hilton Chicago has hosted numerous U.S. presidents (it was known as the Midwest White House) as well as Charles Lindbergh, Queen Elizabeth II, Michael Jordan and JFK, Jr. President Obama gave his victory speech just across the street in Grant Park in 2008 and held numerous press conferences here throughout his campaign. In the lobby is a wall of old black-and-white photos and a timeline of important events in the hotel’s history, as well as artifacts from yesteryear including old menus from the gourmet dining room as well as a photo of the Stevens family. Fun fact: John Paul Stevens, a son of the original owner went on to become a Supreme Court Justice. There is also a display of the many movies that were filmed in the hotel including The FugitiveMy Best Friend’s WeddingRoad to Perdition and more recently, TV shows like Chicago P.D. and Empire.

Rooms & suites 

The Hilton Chicago has a total of 1,544 rooms and suites. I was on the 24th floor and had incredible views out over Lake Michigan and sprawling Grant Park. It was nicely decorated with modern artwork, glass lamps, leather chairs and wooden furnishings. Rooms feature all the high-tech gadgets you’d expect and also come with large flatscreens. My room was on the Executive Level, which has a central communal area with comfy seating and a small kitchen-type area where continental breakfast and evening hors d’oeuvres are laid out each day – these floors are ideal for business people on the go but quite handy even for leisure travelers.

One of the top suites is the Conrad Hilton Suite (above), which is spread out over two levels with a master bedroom and a marble bathroom with a large whirlpool tub. It also has a large dining room as well as a billiards room and bar. When the room is not booked, private events can take place here, which might include cocktail parties, intimate dinners or even a small wedding. I was fortunate to experience a tasting menu beautifully prepared by executive chef Mario Garcia (who started in the kitchen in 1996 and worked his way up to become the top toque in 2010) in the suite that included prawns with ramps and Peruvian peppers, and lamb with sunchokes, wild rice and quinoa. And we topped that off with a plate of Wisconsin cheeses and honey from the Hilton Chicago’s rooftop hives.

hilton chicago

The Hilton Chicago. (Photo: AAA Hotels)

Dining at the Hilton Chicago

In the lobby of the Hilton Chicago is the 720 South Bar & Grill, which is open all day long. The breakfast buffet has just about everything you would want from made-to-order omelets and Belgian waffles, pancakes and pastries along with healthy items like fruit and yogurt. After a day of sightseeing or pre-dinner, you can have a drink in the stylish bar area (above) that overlooks Michigan Avenue. The bar is known for its craft cocktails with names like Mango Fire and Glass Slipper and its small plates menu includes flatbreads, charcuterie and wings. The bar does a brisk after-work business and stays busy well into the evening.

Another place to dine is Kitty O’Shea’s, a classic Irish bar that recently celebrated its 30th anniversary. I was there for the anniversary party and to see the bagpipers performing was quite something! But no matter when you are there, the homey atmosphere and decor – rich woodwork, tiled floors and brass fittings – make it a fun, casual spot (and there’s often live music). Some of the beers on tap include Guinness, Smithwick’s, Harp and Kitty O’Shea’s Red Ale, made specially for the bar. There’s also a wine and whiskey selection and the menu features classics like burgers, fish ‘n chips, shepherd’s pie and corned beef and cabbage.

If you need a quick bite, either a salad or sandwich or even a deep dish pizza or a cup of Starbucks’s coffee you can stop in at Herb N’ Kitchen, which is just off the main lobby — and, of course, there’s always room service.

Event spaces

With a hotel of this magnitude, there are plenty of events going on throughout the day and night, perhaps a wedding, convention or business function. In all, there is 234,000 square feet of meeting space at the Hilton Chicago, which includes numerous state-of-the-art meetings rooms, the International Ballroom and the jewel in the crown of the hotel, the Grand Ballroom. Seeped in history, this spectauclar space boasts 10 gorgeous crystal chandeliers and gilded ceiling accents. The room can accommodate up to 1,000 people and it’s quite the coup to have an event here, especially a wedding.

Nearby attractions

A ten minute walk from the Hilton Chicago brings you to the Art Institute of Chicago, one of the world’s great museums. There are so many famous works here, it truly is mind-boggling. In addition to Marc Chagall’s America Windows (above), three blue-hued stained glass windows created by the artist in 1977, there are several American classics in its collection including American Gothic by Grant Wood and Nighthawks by Edward Hopper as well as several works from Georgia O’Keeffe. In Millennium Park, you can catch an outdoor concert on the Great Lawn and snap a photo of the famous Cloud Gate sculpture, dubbed the Bean. The Navy Pier, is a great spot to grab a bite to eat and take a spin on the Centennial Wheel, a giant Ferris wheel. You can also catch an architecture boat tour from here that goes along the Chicago River, passing the city’s famous skyscrapers. And be sure to do some shopping along Michigan Avenue, a.k.a., Magnificent Mile.

Haven’t been to a Cubs game yet? After Boston’s Fenway ParkWrigley Field, on Chicago’s North Side, is the oldest baseball stadium, built in 1914. I have never been to the stadium so I was excited to be able to catch a game while in town. The weather was perfect for the afternoon game and with a sausage sandwich and a beer in hand, I took it all in: the ivy on the wall, the bleachers on the neighboring buildings and just the fantastic baseball atmosphere in general. To cap it all off, the Cubs won so I got to hear the victory song, “Go, Cubs, Go.”

Later that evening, I caught some live music at Buddy Guy’s Legends and I didn’t even have to venture too far — the venue is just across the street from the hotel. Owned by blues legend Buddy Guy, who was born in Louisiana but made his name in Chicago, the place was packed (Israeli-born guitarist Guy King was the headliner). I got lucky because Mr. Guy made a brief appearance on the stage with Mr. King that night, something I’m told is increasingly rare. After such an action-packed day and night, I was ready to call it a night and was very happy to be heading back to the comfort of the Hilton Chicago.

What are your favorite things about Chicago? Let us know in the comments below!

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