122 W Monroe St., Chicago
The Pitch History runs deep, or rather, tall, at The Gray. In a historical structure originally designed in 1894 by William LeBaron Jenney, the “Father of the Skyscraper,” The Gray is the perfect hotel for those who dream about architecture and design. It is an official Chicago landmark, thanks in part to Preservation Chicago, who added the building to its Most Endangered list in 2002 after several large redevelopment plans had been discussed for the site. A study in pale gray marble and brass, the hotel has eye candy in every corner, from grand light fixtures to lean-lined furniture, and there are plenty of nods to its art deco roots when the building was home to the New York Life Insurance Company.
Gensler, the architecture and design firm that gave the hotel its grandeur, helped convert the space while restoring many historic elements throughout, including the limestone, granite and terracotta-clad façade, which was in disrepair after years of neglect. The Gray opened its doors in the summer of 2016 with 293 luxurious rooms, a salon and day spa, 24-hour fitness centre, two restaurants, and a cocktail and wine bar featuring some of the rarest wines to be found in the city. But while the property is heavy on design it’s low on pretense — even four legged visitors are welcome.
What We Love The Gray just gets the guest experience. When you check in, you have the option to provide your cell phone number so you can text any questions you might have to the concierge. Don’t be surprised to get a text asking how your stay is going. If you forgot to pack something, odds are The Gray can help: It has a long list of items to borrow or use, from cell phone chargers to garment tape to prevent wardrobe malfunctions. The staff are all friendly and outgoing, a team of effusive Chicago advisers. If you ask for pizza recommendations, however, be prepared make some tough decisions (our vote goes to Lou Malnati’s Pizzeria).
Don’t Miss The hotel is home to one of Chicago’s hottest restaurants, Boleo. This sweeping spot on the top floor features a menu of Latin American dishes, perfect for sharing, including some delicious empanadas (don’t miss the vegetarian!). The cocktail list is outstanding (especially amazing pisco concoctions, but the real showstopper is the retractable roof with a view that would thrill the Father of Skyscrapers himself.
Rooms from US$450 per night