Kimpton Gray Hotel

Rooms and decor

Picture a stately gray-stone skyscraper that has stood in the middle of Chicago's financial district since 1894 — the New York Life Building, once one of the world's early high-rises, today home to the Kimpton Gray Hotel, which opened in 2016. The name Gray isn't for show: it comes from the gray Georgia Gray marble that clads the lobby, staircases and common areas, blending a serious classic mood with modern design so well that every corner photographs nicely. Inside, the roughly 293 rooms and suites are done in warm contemporary tones with touches of deep blue and copper, giving a boutique feel you won't find in a standard chain room. Beds are comfortable, the bathrooms are clean and simple, and many rooms have big windows looking out over the skyscrapers and busy streets of The Loop below. Plenty of reviews praise the decor as tasteful and say it feels more special than the price you pay — like staying in a building with a real story rather than just a pretty bedroom.

Food and amenities

The highlight everyone talks about is the Boleo rooftop bar on the top floor — a Peru-themed spot decorated in bright, playful color with a full view of the Chicago skyline. The clever part is the retractable glass roof: open to the breeze and soft sun in summer, closed and cozy in winter, so you can sip a cocktail and take in the view all year. It's one of the neighborhood's popular rooftops, and locals drop by too. Down at ground level, the Steadfast restaurant serves contemporary American food alongside a good cocktail bar. What makes many guests love the Kimpton brand is the free wine hour every evening, when wine is set out for guests to sip in the handsome marble lobby — a relaxed window to say hello to other travelers. Kimpton is also known for being pet-friendly, taking dogs and cats free with no size or weight limit, which is a win if you bring a four-legged friend. There's a 24-hour fitness center too, so all told you can spend the whole day here and still have plenty to do.

Location and getting there

Kimpton Gray sits in the heart of The Loop, Chicago's Financial District, right at the corner of LaSalle and Monroe. This is the dream for anyone who wants to explore on foot — step out the door and you're surrounded by historic skyscrapers and the city's landmark buildings. It's about 8 minutes on foot to Willis Tower, once the tallest building in the world, with its stomach-turning glass Skydeck, and another 10 minutes or so to Millennium Park and the iconic The Bean sculpture everyone goes to photograph. The Art Institute of Chicago and the State Street shopping strip are an easy walk too. Getting around is simple, with several elevated CTA train lines nearby — Monroe station is about a 3-minute walk and connects you across the city and straight out to O'Hare and Midway airports. In short, if you want one base from which to walk or train to the major downtown sights without leaning on taxis, this location is a perfect ten.

Things to know before booking

Straight talk to help you decide. The first thing reviews mention often is that standard rooms run fairly compact, the trade-off for a boutique inside an old downtown building. Some guests feel the space for luggage and storage is smaller than the glossy photos suggest. If you're traveling with several people or want room to spread out, upgrade to a larger category or a suite. The second is the character of the Financial District, which buzzes mainly on weekday daytimes — once offices close in the evening and on weekends, many shops close too and the streets quiet down. For bars and nightlife right outside the door, you'll need to walk over toward River North or State Street, though it isn't far. The last point is the car: the hotel has no parking of its own, so you'll rely on valet, where the downtown Chicago fee runs fairly high for the area. If you're driving in, budget for it, and note that some rooms facing the main street may catch traffic noise in the morning — if you're a light sleeper, ask for a higher floor or the quieter side.

Our take

After reading through hundreds of real reviews, Kimpton Gray Hotel is a boutique that sells "historic-building charm plus a central location plus an easygoing feel" in a way that's genuinely distinctive and good value. If your trip in your head is waking up in a stylish room inside a 100-plus-year-old skyscraper, walking a few minutes to Willis Tower and Millennium Park, coming back for free wine in the marble lobby in the evening, then closing the night with a cocktail over the city on the Boleo rooftop — this is a near-perfect fit, at a price more reachable than the luxury hotels around it. The catches are just the fairly compact standard rooms and a neighborhood that quiets down after dark. Overall we give it 9.0/10, best for couples, business travelers and solo trippers who fall for old buildings with a story and value location and atmosphere over room size.