The Guesthouse Hotel

A Hotel Built Like a Neighborhood Apartment

Most hotels this close to downtown Chicago rent rooms. The Guesthouse Hotel rents a version of actually living in Andersonville, the Swedish-rooted, independent-shop-heavy neighborhood the Chicago Reader named the city's best hotel address in 2024. All 25 units are one- to three-bedroom suites rather than standard rooms, each with a full kitchen, in-unit laundry and a private balcony, built for guests who want a few days or a few months rather than a single overnight. Across the street, the 38-acre St. Boniface Cemetery offers one of the quietest green spaces in the city, an unlikely but genuine amenity for a property this central.

Why It Works

What earns this hotel its place is how completely it commits to the apartment concept instead of treating it as a gimmick. Even the smallest suite clears 600 square feet with 10-foot ceilings, and larger units add multiple bathrooms, gas grills and full-size washers and dryers, the kind of specification that actually supports an extended stay rather than just advertising one. A seasonal rooftop deck adds a skyline view the all-suite format might otherwise lack, and the fireplace-lit club room hosts an afternoon tea with Vanille Patisserie that gives even a one-night guest a reason to linger downstairs.

Why This Location

Andersonville runs on independent businesses rather than chains, with Swedish bakeries, bookshops and a dense restaurant scene within a few blocks in every direction, and Lincoln Square, Ravenswood and Uptown all reachable on foot or a short ride. It is a genuinely residential stretch of Chicago rather than a tourist corridor, closer in feel to a neighborhood someone actually lives in than to a hotel district. Downtown and the Magnificent Mile sit a train ride south, but guests who choose Andersonville are usually choosing it on purpose, not settling for a less central address.

Fast Facts

• Price: Luxury

• Vibe: Residential, condo-style, neighborhood-first

• Rooms: 25 one- to three-bedroom suites, all over 600 square feet

• Best For: Extended stays, travelers who want a kitchen and real space, families

• Our Favorite Thing About the Hotel: The seasonal rooftop deck looking out over the Chicago skyline

• Dining: Afternoon tea with Vanille Patisserie in the library or club room, full in-suite kitchens for guests who want to cook

• Amenities: 24-hour fitness center, private balconies, in-unit laundry, gas grills, pet-friendly with complimentary dog beds and bowls

• Attractions: St. Boniface Cemetery, Andersonville's independent shops and bakeries, Lincoln Square, Ravenswood

Rooftop Views and Afternoon Tea

The seasonal rooftop deck is the hotel's clearest nod to the skyline it otherwise keeps at a neighborhood's distance, open in warmer months for views that most all-suite properties this size do not bother offering. Inside, the club room, with its fireplace, crystal lighting and vintage leather seating, hosts an afternoon tea built around pastries from Vanille Patisserie, scaled for small groups in the library or gatherings up to fifty in the club room itself. It is the kind of detail that turns an apartment-style stay into something closer to a members' club for the length of a visit.

Suites That Work Like Apartments

All 25 units run one to three bedrooms, with even the smallest suite exceeding 600 square feet and 10-foot ceilings, numbers that put most Chicago hotel rooms to shame. Full kitchens with stainless appliances, in-unit washers and dryers, and private balconies come standard, and larger suites add multiple bathrooms and gas grills for guests entertaining or settling in for weeks rather than days. Housekeeping is optional rather than automatic, a small but telling sign that the hotel is built around how residents actually live, not how hotel guests are expected to behave.