Chicago, IllinoisChicago Loop
Staypineapple, an Iconic Hotel, The Loop Chicago
Landmark skyscraper showcase
Chicago Loop Chicago, Illinois
Opened
1999
Price
$$
Rated for
Heritage Design LocalOutside the door
The house
StaypineappleLandmark skyscraper showcase
Chicago School architecture meets playful yellow accents inside the 1895 Reliance Building, complete with original mosaic tiles and wrought-iron elevator cages.
What it’s good at
Remarkable
Occupies the landmark 1895 Reliance Building with preserved wrought-iron elevator cages and original mosaic tile floors.
Notable
Pioneering Chicago School architecture features large bay windows and historic office transoms alongside bright yellow decor.
Listed
Set at State and Washington in the Loop, offering yellow cruiser bikes for rides to Millennium Park.
In a lively part of town
Where things happen: restaurants, shops, people.
The Chicago Theatre and Millennium Park sit just steps away, easily explored on foot or aboard the hotel's bright yellow cruiser bikes.
The rooms
Expansive bay windows flood spaces with daylight, framing vintage glass transoms, historic office mail slots, and European-style dual individual duvets.
The gym
- Gym
- 24-hour on-site fitness room with cardio equipment and light strength machines; complimentary yellow city cruiser bicycles available for guest use.
Dogs stay too.
Restaurant
Atwood
Twenty-four-foot windows overlook the corner of State and Washington, where Atwood serves American classics and craft cocktails.
How it began
Completed in 1895, the landmark Reliance Building pioneered steel-frame construction and expansive glass facades that prefigured modern skyscrapers.
Good to know
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Staypineapple, an Iconic Hotel, The Loop Chicago
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Our shorthand
How we rate hotels.
The medals
Gold
Extremely rare. Sets the global standard.
Silver
Brilliant execution. And we’re picky.
Bronze
They did this well. You’ll notice.
Listed
A defining trait. Makes the hotel what it is.
The eight vibes
Design
Built around a vision. Even the door handles have a designer.
Luxe
Cared for at every turn. The bath is drawn before you ask.
Local
It could only be here. You wake up knowing where you are.
Social
Where the city goes out. The bar is full and the night is young.
Heritage
A building with a story. Once a palace, a monastery, a station.
Wellness
You leave feeling new. Rest, sweat, soak and sleep like a stone.
Classic
The city grew up with it. Same rituals, same regulars, same bar.
Resort
A world of its own. Something to do from breakfast to nightcap.
The scene
Lively
Where things happen: restaurants, shops, people.
Central
Well-located: walkable to some things, a short ride to more.
Quiet
Away from the crowds. Getting around takes intention.
Secluded
A place apart: the property is the destination.