LET’S GO STAYPINEAPPLE CHICAGO: WINNER IN USA TODAY 10BEST FOR TWO YEARS RUNNING!

For the second year in a row, Staypineapple Chicago has been honored as one of the Best Boutique Hotels in the USA TODAY 10Best Readers’ Choice Awards! Nominated by a panel of travel experts and voted on by guests like you, we ranked #3 among 20 of the best boutique hotels in the nation – and proudly claimed the #1 spot in Chicago.

If you’ve stayed with us in Chicago before, you already know the charm –  a beautifully restored historic building with timeless design and modern Staypineapplized touches, paired with exceptional and personalized service for an unforgettable stay. We’re committed to living up to the title of Best Boutique Hotel by continuing to provide outstanding accommodations and memorable experiences – not just here in Chicago, but at all 10 of our hotels across the country.

Book your stay today (and tell everyone you know you’ve stayed at an award-winning hotel – two years running)!