The modern and revamped Chicago Athletic Association is considered one of the most beautiful boutique hotels in Chicago. Cindy’s rooftop restaurant, with its spectacular view of Lake Michigan and Millennium Park, is a favorite spot among locals. Or, grab a drink at the Cherry Circle Room, the Shake Shack, or the Game Room, which has great cocktails alongside game tables.
If you’re looking for a boutique hotel that feels like you’re just crashing at a friend’s house, the Freehand Chicago is designed like a super-cool friend’s living room. Located in the center of the River North area, it's a short walk from a number of major attractions, and one of the best restaurant districts in the city. For a quick snack, grab a coffee and pastry at the adjacent Café Integral.
Nestled in an area of mega-hotels and rental properties, The Publishing House Bed and Breakfast offers a much more personal touch than other hotels in Chicago. Choose from one of the 11 uniquely designed rooms, outfitted in stylish vintage furniture. The incredible breakfast cooked by the hotel owners is one of the highlights, as is their exceptional personal service.
The Staypineapple in Chicago’s eclectic Loop is situated in the Reliance Building, listed on the National Register of Historic Places. The modern design seeks to reclaim some of the building’s historic features, including the original ornate grillwork on the elevators. On your way out to explore Chicago, stop at the Pineapple Espresso for a quick cup of coffee and a snack.