(This post was updated in January 2020.)

Pineapple Hospitality Group is a small boutique-hotel chain you should know.

The family-owned hotelier, founded in 2011 and based in Bellevue, Wash., operates eight unique hotels in prime locations across the country. Seven are on the West Coast. The newest is a historic Midwestern property–The Alise Chicago, now known as StayPineapple Chicago, the city’s downtown Loop. The hotels are different but significant architecturally, and they all promise the luxurious “StayPineapple Difference.”

My husband and I were recently hosted by StayPineapple Chicago for an overnight and dinner at their Atwood restaurant. We were delighted by the comfort and quality of our accommodations, the inventive and diverse menu offerings, the extensive cocktail creations and the impeccable meal service.

In between were surprise amenities: complimentary cupcakes and coffee in the lobby, yellow seersucker bathrobes in our room. Apparently, that’s just how StayPineapple does things.

(Pineapples have been a symbol of high hospitality since the Colonial era of our country, when the fruit was both expensive and rare. If your host could afford to serve pineapple, you were in for a grand time.)

The 14-story, 122-room StayPineapple Chicago occupies the city’s historic Reliance Building at the intersection of State and Washington streets. It’s been designated as a national, state and city landmark.

Built between 1890 and 1895, the building is credited as a forerunner to modern-day skyscrapers. Portions of it were designed in turn by venerated architects Daniel Burnham, John Root and Charles Atwood. The terra cotta facade is punctuated with enormous bay windows and horizontal spandrels. The interior is lavished with ornate wrought iron grillwork, mahogany woodwork and marble walls and stairs.

The building fell into disrepair by the 1990s and then underwent a couple of restorations and remodelings. Pineapple Hospitality Group bought and renamed the former Hotel Burnham in 2016. They pineapple-ized the premises with new protocols, luxe beds and linens, and custom artwork while retaining the building’s architectural integrity.

StayPineapple Chicago has been infused with a playful and light-hearted vibe. Take, for example, the Naked Experience. That means you should be as comfortable, safe and uninhibited within your room as you would be at home. The linens are snuggle-worthy: Individual European-style duvets, comfy pillows, fluffy towels. They call it the grown-up version of your favorite blankie. (The door-hanger reads on one side: “I’m Naked. Please go away.”)

Our Room 1504 was a corner suite with a separate living area and bedroom. From the window we could glimpse Lake Michigan at the eastern end of Washington Street. The furnishings included a sofa, cocktail table, desk and office chair, king-size bed, two flat-screen televisions, refrigerator and Keurig coffee maker. Among the bath appointments were a large back-lit mirror and sustainable Tommy Bahama toiletries.

But before we slept, we dined at the Atwood restaurant on the first floor. The 24-foot windows on two sides were perfect for people-watching along one of the most well-known streets in the world. (You know the song: “State Street, that great street…”) The decor is modern vintage, combining hardwood floors, marble tabletops, white subway tile walls and artistic light fixtures.

The bar alone is worth special mention: Seven signature drinks and the Atwood 50, a selection of classic libations. Come on, when it the last time you had a Singapore Sling or a Sazerac?

The smoked trout dip was intensely flavorful without being fishy. The kale salad with strawberries, goat cheese, almonds and horseradish vinaigrette was light and fresh. We both ordered fish as our entrees: pan-seared halibut with American caviar, Parisian gnocchi, radish and bitter greens; and crispy salmon with melted leeks and celery root puree. Both were delicious. After watching the servers whiz past us with plates of baked Alaska all night, we knew we had to have that, too. You have a choice of vanilla or dark chocolate ice cream. Yum.

Overall, our night at StayPineapple Chicago and Atwood was both luxe and memorable. A beautiful place for a romantic getaway! If you have the opportunity, StayPineapple.