This quirky Chicago property was named one of the best boutique hotels in the country

Chicago’s hotel scene has earned plenty of national accolades, and one quirky local property just scored high in a ranking of the country's best boutique hotels. Staypineapple Chicago has been named the number four best boutique hotel in the U.S. in USA Today’s 10Best Readers’ Choice Awards. Selected by a panel of travel experts and voted on by readers, the award highlights independent properties that deliver customized service, character and modern luxury.

Housed inside the historic 1895 Reliance Building at 1 West Washington Street, Staypineapple Chicago seamlessly pairs pioneer-era skyscraper architecture with playful, modern design. Original structural details—such as intricate wrought-iron elements, pristine mosaic tile floors and a light-filled lobby—stand side-by-side with bold, saturated yellow-and-white decor. The chain's signature pineapple motif can be spotted throughout the property, subtly integrated into everything from throw pillows and lamp bases to ceramic mugs.

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The guest experience prioritizes supreme comfort and whimsical hospitality. Every room and suite features Staypineapple’s hallmark European-style individual duvets, lightweight robes and plush bath towels designed for relaxation after exploring the city. Pet lovers are equally pampered: through the hotel’s signature Pineapple Pup Package, four-legged friends receive a dedicated dog bed, collapsible water bowl and a generous stash of treats for their stay.

While Staypineapple claimed the fourth spot in the nation, three other standout properties led this year’s top rankings. The Graylyn Estate in Winston-Salem, North Carolina earned the number one spot. A 55-acre historic sanctuary often described as North Carolina’s own "Downton Abbey," The Graylyn offers 24/7 butler service, an on-site fishing pond and famous homemade butterscotch cookies. The Beatrice in Providence, Rhode Island and Bottleworks Hotel in Indianapolis, Indiana round out the top three.

But locals know that whether you're visiting Chicago for iconic architecture, award-winning restaurants and bars, sports or culture, Staypineapple is the spot for a memorable, one-of-a-kind boutique stay in the heart of The Loop.

The best boutique hotels in the U.S., according to USA Today

1. The Graylyn Estate—Winston-Salem, North Carolina
2. The Beatrice—Providence, Rhode Island
3. Bottleworks Hotel—Indianapolis, Indiana
4. Staypineapple Chicago—Chicago, Illinois
5. Hotel Trundle—Columbia, South Carolina
6. Inn at Stonecliffe—Mackinac Island, Michigan
7. Rusty Parrot Lodge and Spa—Jackson, Wyoming
8. Hotel Fauchère—Milford, Pennsylvania
9. Colony Hotel—Palm Beach, Florida
10. Hotel Peter & Paul—New Orleans, Louisiana