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Where to stay in Chicago from a Chicagoan - The Kimpton Gray

When it comes to places to stay in downtown Chicago, there are endless options when it comes to location, style, size, and luxury status. As a Chicagoan, the one hotel my wife Bari and I keep coming back to is The Kimpton Gray in the heart of the Loop. The decor, historic vibe, quaintness, and just about everything about it makes you feel like you’re in a special place, and the staff is some of the kindest, most welcoming hotel staff you will find. They go out of their way to make each guest feel at home.

The Kimpton Gray gives off the energy of just wanting to look and be your best. Of course, the decor helped inspire me to take some incredible photos matching a custom suit to the backdrop.

The Kimpton Gray Hotel is a special place to me because it is where I proposed to my wife! It’s also where I shot the photos and videos for my premium hat brand, Vandre. Needless to say we love all things about The Gray!

Below you'll find in-depth information on The Kimpton Gray Hotel, Vol. 39 and Boleo

The Kimpton Gray Hotel

When you enter The Kimpton Gray Hotel you’ll marvel at the grand marble entrance that is used as a backdrop for endless wedding photos. Progressing through to the lobby area, the reception desks blend in perfectly. Most of the decor is transported from France or Italy and you may start to notice a subtle elegant butterfly theme throughout.

One notable part of checking into the hotel is the Pup Stop! The Kimpton Gray is a dog friendly hotel that welcomes all furry friends with tennis balls, treats, and anything else your pup may need! They treat all pups with the utmost hospitality, which surely sets them apart from other hotels.

The rooms in the hotel are upscale and elegant all without being stuffy, and they include many desirable features and amenities, including a Nespresso coffee machine (because any other kind would just not do), a fluffy and cozy bed, thick plush bath robes, and overall modern aesthetic and design. The rooms capture the beauty and history of the city, as well as the building itself.

Below are some incredible pictures of the Presidential Suite that we stayed in, but you’ll see many of the same elements from the suite in all of the hotel rooms.

When you walk through the main lobby area of the hotel, you’ll notice a lot of people working or relaxing. Make it your own space and enjoy the oasis in downtown Chicago.

The Gray cares about the little things. They care about every detail. They took this philosophy to the next level with our Director of Concierge Services, Bobby Gonzalez. He is an award winning concierge and genuinely one of the kindest person. He's even been there since the hotel opened, so that should say it all! Even the bottled cocktails they sell at the front desk are handcrafted with a purpose by Bobby himself. $1 from every bottle sold is donated to rotating charities. Check out all the details here: click here.

The Kimpton Gray is also home to some incredible dining options without ever having to step outside. All the details are below, but be sure to check out Vol. 39 for cocktails and Boleo for lunch or dinner!

Vol. 39

Located on the second floor of The Gray, Vol. 39 captures the timeless elegance of mid-century Chicago and has some of the best cocktails in the city. Vol. 39 surpassed our previous favorite cocktail bar that we have been going to for years. For Bari and I, this is a HUGE accolade. We take our cocktails very seriously and so does Vol. 39.

They have truly mastered it all — from the decor to the ice they use in their cocktails. Vol. 39 is NOT your typical hotel bar. It is an upscale cocktail bar with an incredible selection, and its plush tufted leather couches, navy accent walls, and endless displays of old books transport you to what you could only wish was your work from home library where you can sip fancy cocktails and smoke a cigar (but no, you can’t actually smoke in there).

Push yourself to order something you wouldn’t typically order and make sure to talk to the server about their recommendations. Our two favorites are the Mezcal Old Fashioned and the Fennel Countdown—truly the smoothest and flavorful cocktails you’ll find in the city There’s something on the menu for everyone.

Although the cocktails are on the pricier side, they are worth every dollar. Indulge, enjoy, and take in the classy vibes.


Boleo, the rooftop bar and restaurant at The Gray, holds a special place in my heart because I proposed to my wife there. I orchestrated a masterful series of lies that involved a fake Tie Bar photoshoot turned proposal. I selected The Gray as the location because The Tie Bar had a retail store at the street-level at the time, and I loved seeing the collaborations between The Tie Bar and The Gray.

Boleo was the first place I thought of to pop the question, and the team was readily available to help make the space available. I’ll let the photos speak for themselves. After the proposal, we took pictures right outside the Board of Trade and we went back later in the week to eat and drink at Boleo to relive the moment.

With its Argentinian-inspired food with dramatic flavors, bold cocktails and stunning rooftop, Boleo is the perfect spot to go to with colleagues after work during the week or for weekend date night with your spouse or significant other. You won’t regret ordering the empanadas, ceviche and crispy yuca fries.

Take the 15-story elevator ride to the top of The Kimpton Gray Hotel for this urban escape. You’ll know you’re in the right place when all you smell are the delicious Latin-American creations.


The Kimpton Gray Hotel is centrally located in Chicago’s business district, otherwise known as the Loop. Just outside the hotel doors you can see the famous Chicago Board of Trade and easily walk to major Chicago attractions. It is easy to get a cab or ride share and you’re not surrounded by tourists the second you walk outside of the hotel.

During the week, the Loop is buzzing with business men and women from across the globe. On the weekends, the Loop calms down and it is very easy to get around. The benefit of being centrally located in the Loop on the weekend is that you are still walkable to all the major Chicago attractions.

Below are several Chicago attractions in the area:

Within 1 Mile

  • Chicago River Walk

  • Michigan Avenue Shopping

  • Maggie Daley Park

  • Buckingham Fountain

  • State Street Shopping

  • Field Museum

  • Navy Pier

  • Shed Aquarium

  • Grant Park

  • Willis Tower

Within 2.5 Mile

  • Millennium Park

  • Adler Planetarium

The post is in partnership with The Kimpton Gray Hotel and was part of a direct outreach regarding our interest in celebrating a staycation with them.


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