Kimpton Gray Hotel Chicago, an IHG Hotel

A Landmark by the Architect Who Invented the Skyscraper

William Le Baron Jenney is the architect historians credit with the first true steel-frame skyscraper, and the 1894 New York Life Insurance Building at Monroe and LaSalle is one of the few of his early towers still standing. It was nearly lost: slated for demolition in the early 2000s before Chicago Landmark status and a later $106 million restoration by KHP Capital Partners, with Gensler leading the architecture and Kimpton's Ave Bradley directing the interiors, turned it into the Kimpton Gray in 2016. The hotel's name borrows its color from the building's original Georgia gray marble, which still lines the lobby and guest-floor corridors today.

Why It Works

Most hotel-in-a-landmark stories amount to a preserved facade wrapped around an interior that could belong anywhere. This one does not: the original LaSalle Street lobby keeps its marble staircase, coffered ceilings, decorative plaster, brass elevator grates and 1920s wrought-iron stair railings, and the restoration team went further, finding leather-bound legal books and encyclopedias left behind by the building's decades of law-firm tenants and building them into the bar rather than discarding them. That is the difference between a renovation that respects a building's past and one that merely photographs well next to it.

Why This Location

Monroe and LaSalle sits at the heart of the Loop's financial district, an easy walk from the Art Institute of Chicago and Millennium Park to the east and the Loop's theatre row to the north. It is inside the elevated-train loop that gives the neighborhood its name, with multiple CTA lines within a few minutes on foot, and close enough to City Hall and the Board of Trade that the surrounding blocks still feel like the working center of the city rather than a tourist corridor.

Fast Facts

• Price: Upper-midrange to premium

• Vibe: Landmark Loop architecture with a confident, design-forward Kimpton restoration

• Rooms: 297

• Best For: Architecture-minded travelers, Loop business trips, anyone who wants a serious hotel bar

• Our Favorite Thing About the Hotel: Vol. 39, the lobby bar built around the building's own abandoned law library

• Dining: Vol. 39 (lobby bar, caviar and charcuterie); Boleo, a South American rooftop restaurant on the 15th floor

• Amenities: Fitness center, concierge, valet parking, pet-friendly rooms, event space

• Attractions: Art Institute of Chicago, Millennium Park, the Loop theatre district, the financial district

The Books in the Bar

Vol. 39 takes its name from the building's original address, 39 South LaSalle Street, and its signature detail from what the construction crew found rather than what a designer sourced: shelves of leather-bound legal volumes and encyclopedias left by the law firms that occupied the building for most of the twentieth century, now displayed throughout the bar alongside gilded silver carts carrying caviar and charcuterie. It is a small thing, but it is the kind of detail that separates a hotel that tells its building's real history from one that simply borrows its address.

A Rooftop Under Glass

Boleo, the hotel's 15th-floor restaurant, runs a South American menu under a roughly 4,000-square-foot glass roof that opens to the sky in good weather, with Loop skyline views in every direction. It gives the hotel a genuine rooftop scene without asking guests to leave the building, and pairs naturally with Vol. 39 downstairs for a two-stop evening that does not require stepping outside.

Before You Book

This is a landmark building retrofitted for modern hotel use, which means room shapes and sizes vary more than in a purpose-built tower — worth asking about when booking if a specific layout matters. Valet parking is the only on-site option in a neighborhood where street parking is scarce and expensive regardless. In exchange, guests get one of the most architecturally serious hotels in the Loop, built around a building most of its competitors can only imitate.