Founded by former Wicker Park residents, it's no surprise that Kinn Guesthouse makes Milwaukee-bound Chicagoans feel right at home. The boutique hotel has eight rooms, each with unique art, colorful furniture and playful touches; some even feature exposed Cream City brick and pieces from Milwaukee artists. Every single comfort is accounted for, and the little touches (Cowshed products in the bathrooms! Apple TVs in every room! Luxury bedding!) make this small Bay View inn shine. All guests are able to access the shared gourmet kitchen and self-serve laundry room, two major travel perks that the big-box hotels don't have.