Editorial score of 8.9 of 10, the composite average of the three factors above (Rooms, Service, Location). Method at our methodology page. Affiliate disclosure: booking links may earn us a commission at no extra cost to you, and never change our verdict.
Why choose the Kimpton Gray Hotel?
Kimpton Gray is the smart choice for the traveller who wants character over convention in the Loop, and its two defining assets are the building and the location. The hotel occupies a landmark at 122 West Monroe Street that once served as the Chicago headquarters of the New York Life Insurance Company, in the heart of the Financial District, and its conversion kept the historic architecture while pulling contemporary rooms into it. The signature feature is the glass: floor-to-ceiling windows in the guest rooms bring the Loop's streetscape and sky into the room, an immersive relationship with the city that standard hotel construction rarely achieves. The rooms are genuinely spacious, with select categories offering separate living areas and spa baths.
The second asset is the Kimpton service model, which is warm and personal rather than corporate. There is a complimentary evening social hour in the lobby, attentive front-of-house staff and a pet-friendly policy that extends to all sizes, all of which justify the small premium over the Loop's chain alternatives. The property adds a fifteenth-floor rooftop restaurant and a law-library-styled lobby bar that give it a night-time draw beyond its own guests, and a fitness centre available around the clock. This is an upscale four-star boutique rather than a full-service five-star, so it trades a spa and a grand lobby for personality and a landmark address, which is exactly the point.
What are the best rooms to request?
Request a high-floor room and prioritise the windows, because the floor-to-ceiling glass is the whole idea here. The 293 rooms mix historic character with a considered modern fit-out, and the higher you go the more the Loop reads as a plan of towers and streets below rather than a wall of neighbouring facades. Entry categories are comfortable and generously sized for a downtown boutique, and the step up to the larger rooms and suites buys separate living areas and spa baths that make a longer or celebratory stay far more comfortable. Beds and bedding are calibrated for genuine sleep rather than photography, which matters more than it sounds in a business-heavy hotel.
One honest caveat. This is a converted historic building, so room shapes and window placements vary and a handful of lower rooms look into the tight canyons of the Financial District rather than out over it. The hotel has no spa and no pool, and the Loop itself empties in the evening once the offices close, so travellers who want a resort-style base or a lively after-dark doorstep should weigh that. Ask for a high floor away from the light wells, and the character-over-convention trade lands firmly in your favour.
Ask for a high floor with the fullest window exposure, and time a drink at Boleo on the fifteenth floor for sunset, when the retractable roof is open in warm weather. Catch the complimentary evening social hour in the lobby for a glass before dinner, and note that Millennium Park and the Art Institute are close enough to fill a free morning on foot.
What is the dining and the bar scene like?
For a boutique its size, the Gray punches above its weight on drinking and dining. The showpiece is Boleo, the fifteenth-floor rooftop restaurant and lounge, a Latin-influenced kitchen and cocktail bar set under a retractable glass roof that opens in warm weather and keeps the room going year round when it is closed, with vibrant music and a design-led fit-out that pulls in a crowd beyond hotel guests. Down in the lobby, Vol. 39 is a bar styled after a law library, a fitting conceit in the Financial District and a genuinely characterful spot for a nightcap or a meeting over cocktails. The Kimpton evening social hour rounds out the in-house offer, and the density of the Loop means a quality restaurant at any price point is rarely more than a ten-minute walk away.
Does it have a spa, pool or gym?
The Gray keeps its wellness offer focused. There is a fitness centre available around the clock, well suited to the business travellers who make up much of the clientele, but the hotel has no spa and no swimming pool, which is normal for a boutique of this scale in a converted landmark. Guests who want a full spa and pool should look to the Magnificent Mile five-stars a short ride north. For a Loop stay built around location, character and a strong rooftop bar rather than a wellness itinerary, the Gray is calibrated exactly right.
Signature amenities
In the heart of the Loop
The Loop · Financial District
What's nearby
- The Rookery Building
Landmark lobby3 min walk - Chicago Board of Trade
Art Deco landmark4 min walk - Willis Tower
Skydeck views6 min walk - Art Institute of Chicago
World-class museum8 min walk - Millennium Park
The Bean & Pritzker Pavilion9 min walk
The building, the rooms, the rooftop
Landmark
Window room
Boleo rooftop
Vol. 39 barHow does the Kimpton Gray compare with Chicago's other boutique hotels?
Against the field, the Gray is the character-led Loop value pick, and the choice between the city's boutiques comes down to neighbourhood and mood. Virgin Hotels Chicago is the other Loop option, more energetic and playful, with the Commons Club bar and its dressing-room-within-a-room layout. Soho House Chicago is the West Loop members' club that admits hotel guests, built around restaurant and rooftop access rather than a traditional front desk. The Gwen Chicago is the design-led Magnificent Mile boutique with an Art Deco pedigree and a more uptown address. The Gray's own trade-off is that it has no spa or pool and sits in a business district that quietens after dark.
| Hotel | Style | Best for | Trade-off |
|---|---|---|---|
| Kimpton Gray Hotel | Landmark Loop boutique | Character, business, value | No spa or pool; quiet after dark |
| Virgin Hotels Chicago | Playful Loop lifestyle | Bar scene, clever rooms | Less traditional service |
| Soho House Chicago | West Loop members' club | Restaurants, rooftop pool | Club-first, fewer rooms |
| The Gwen Chicago | Art Deco Mag Mile boutique | Design, uptown address | Higher rates |
Frequently asked questions
What building is the Kimpton Gray Hotel in?
The hotel occupies a landmark Loop building at 122 West Monroe Street that once served as the Chicago headquarters of the New York Life Insurance Company. Its conversion kept the historic architecture while adding contemporary guest rooms, and the building gives the hotel its signature floor-to-ceiling windows over the Financial District.
How many rooms does the Kimpton Gray Hotel have?
There are 293 rooms and suites, with select categories offering separate living areas and spa baths. The floor-to-ceiling windows are the defining feature, pulling the Loop's streetscape into the room, and the interiors mix historic character with a considered modern fit-out.
What are the restaurants and bars at the Kimpton Gray Hotel?
Boleo is the fifteenth-floor rooftop restaurant and lounge, a Latin-influenced kitchen and cocktail bar under a retractable glass roof. In the lobby, Vol. 39 is a bar styled after a law library, and the hotel runs Kimpton's complimentary evening social hour.
Is the Kimpton Gray Hotel good for business travellers?
Yes. Its Financial District address, spacious rooms with real working space, the evening social hour for informal colleague conversations, and a 24-hour fitness centre make it one of the Loop's most complete business hotels, with Millennium Park and the Art Institute within a short walk for client entertainment.
Where is the Kimpton Gray Hotel located?
At 122 West Monroe Street in the Loop, the heart of Chicago's Financial District. Millennium Park, the Art Institute of Chicago, the Chicago Riverwalk and the Willis Tower are all within a short walk, and Union Station is roughly ten minutes on foot for Amtrak connections.
Other luxury stays in Chicago
#8 · LoopVirgin Hotels Chicago
#6 · West LoopSoho House Chicago
#11 · Mag Mile