Prominently centered in the financial district, this handsome historical landmark formerly home to the New York Life insurance building received a sleek, bespoke redesign appealing to young professionals with discerning tastes.
YOU SHOULD KNOW Among the property perks include a complimentary pet policy with on-site services like doggy daycare, walking, grooming, treats from the pastry chef, and pet beds. The property also offers a handful of complimentary bikes on a first come, first serve basis.
A nod to its business-centric enclave, rooms feature a blend of masculine and feminine design elements riffing off classic suits. Think splashes of dark blue with white with floral lining and veneer surfaces. For guests on the go, rooms are outfitted with yoga mats and the mini-bar features Tie Bar ties for purchase.
YOU SHOULD KNOW On the way to your room, try to spot a "stair to nowhere" located on each floor. The stairs are original, but remodeled for room space and now blockaded with a piece of art.
Sleek brass fixtures on standing showers and tiled floors blend old and new, with soft, cozy Frette robes to dry off in comfort. "Keep calm, it's just garlic" artwork might seem out of place, but it's intentional: a subtle reference to the building's history, which used to be on a garlic mine.
Upgrading to a corner suite will score you a gorgeous deep-set porcelain soaking basin with city views.
Head to the second floor to check-in and a spacious lobby with clean lines and high-vaulted ceilings. Most of the original design has been remodeled with a mishmash of colorful vintage and contemporary inspired furniture, but touches of the historic building remain like original ceiling reliefs and vintage car signs on the elevators.
YOU SHOULD KNOW Every Kimpton property hosts a happy hour from 5 p.m. to 6 p.m. with complimentary red and white wine. The Gray is unique in that they will often have a cellist come in to play.
On the street level, you'll find Steadfast, a chef-driven New American restaurant that also handles in room dining. Don't miss rooftop Argentinean restaurant Boleo, featuring an incredible seasonal retractable roof for tasting grilled meats and specialty fernet.
YOU SHOULD KNOW Plan accordingly: Boleo is only open Wednesday through Saturday and tends to get busy at peak hours.
Vol. 39 boasts one of the best cocktail programs in the city, known for its Old Fashioned specialty menu. Take note of the rows of vintage law books lining the leather tufted couches; the collection was discovered in the basement of the property, including Vol. 39, which the bar is named after.
Conveniently central in the Loop, the property is steps away from all Chicago L trains and buses. Taxis are easily accessible in this area, as well as ride-hailing apps if you need to get somewhere quickly. Valet and parking garages are nearby, but can be quite pricey and a hassle if you're spending most of your time downtown.
The once-sleepy Financial District dominated by lunch restaurants is finally seeing up-and-coming restaurants like Cochon Volant Brasserie (1-minute walk) and trendy food halls like Latincity (4-minute walk) and Revival Food Hall (2-minute walk). Classic standbys abound like Italian Village (1-minute walk) or The Grillroom Chophouse & Wine Bar (3-minute walk), but foodies seeking the latest hotspots should head to River North.
Boasting three of the top places to grab a drink in the Financial District, it's worth staying on-site to grab a drink. Must you leave, the after-work crowd can be found at upscale wine bar Townhouse Restaurant & Wine Bar (6-minute walk) or divey favorites Franklin Tap and Cactus Bar & Grill (8-minute walk).
WHY WE LIKE IT
For buttoned up business travelers loaded with meetings, it can be difficult to squeeze in time to enjoy a city. But sleek, comfortable accommodations with three incredible dining options can make even the busiest guest feel like they've had a worthwhile taste of Chicago. Thoughtful perks like a complimentary happy hour and bike rentals have a welcoming VIP touch you won't find at standard chains, along with enviable upgrades like a luxe soaking basin you'll wish you could take home.