Staypineapple, An Iconic Hotel, The Loop Chicago

Staypineapple, An Iconic Hotel, The Loop Chicago

1 W Washington St, Chicago, IL 60602, South Chicago, United States

4-star hotel

Guest rating: 4.6 / 5

Overview

Staypineapple, An Iconic Hotel, The Loop Chicago occupies a landmark 1895 skyscraper in Chicago's Loop, blending original architectural character with a colorful, playful hotel concept. The 4-star property sits in the heart of downtown, less than 400 feet from the nearest El Train stop, making it a convenient base for exploring the city. It has earned a strong 4.6 rating from 2,343 reviews, with guests frequently praising the historic building and central setting.

Rooms

Guest rooms are colorful and stylishly decorated, each equipped with a work desk, a laptop-sized safe, and a 37-inch flat-screen TV. Some suites offer views of Lake Michigan along with a separate living room area, suited to guests wanting extra space. In-room Wi-Fi is included at no charge for guests who join the hotel's free membership program.

Dining & Freebies

The hotel houses a modern American restaurant on site, and guest reviews consistently describe the food and bar program as high quality. A complimentary evening wine hour and morning coffee and tea service are included for guests, adding a hospitable touch to the stay.

Amenities & Recreation

On-site facilities include a gym and in-room spa treatments available for an additional fee. Retro bicycles are available for guest use, and a reusable water bottle station is offered in the lobby.

Location

The hotel is exceptionally well positioned for sightseeing, sitting 474m from Millennium Park, 411m from Cloud Gate, 618m from the Art Institute of Chicago, and 784m from both Willis Tower and Skydeck Chicago. The Chicago Theatre and Chicago Cultural Center are each under 300m away, while the Field Museum, Shedd Aquarium, Navy Pier, and Adler Planetarium are all within roughly 2km, and the Chicago Riverwalk is a short 735m walk.

Best for

This hotel best suits leisure travelers and sightseers who want to walk to Chicago's major landmarks, given its proximity to Millennium Park, Cloud Gate, the Art Institute of Chicago, and Willis Tower, plus easy access to the El Train. It also appeals to design-minded guests who appreciate historic architecture paired with a playful, boutique atmosphere, and to pet owners, as the property is noted as pet friendly.

Travel tips

The hotel's location less than 400 feet from an El Train stop makes it easy to reach neighborhoods beyond downtown without a car. Many top attractions, including Cloud Gate, Millennium Park, the Chicago Theatre, and the Chicago Cultural Center, are within a 5-10 minute walk, so comfortable shoes are worth packing over renting a car. Guests headed to the Field Museum, Shedd Aquarium, Adler Planetarium, or Navy Pier should plan for a longer walk of roughly 2km or a short rideshare/transit trip.

What guests say

Guests consistently highlight the hotel's outstanding central location, historic architecture, friendly and accommodating staff, and comfortable beds, along with praise for the on-site restaurant and bar. Complimentary touches like the wine hour, morning coffee, retro bikes, and reusable water bottles are frequently called out as pleasant surprises. Some reviewers feel the property delivers more like a boutique 2-star experience than a full 4-star one, pointing to issues such as worn carpeting, a poorly maintained tub, malfunctioning outlets, a sagging or oddly scented mattress, gym equipment in poor condition, and questions about how often bedding is laundered. A few guests also raised concerns about room key security and an elevator outage affecting this historic building.

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