The Best Boutique Hotels in Illinois (2023)

Why We Like It: Where Chicago’s new coolest neighborhood, Andersonville, meets Lincoln Square, Uptown and Ravenswood lies the unassumingly titled Guesthouse Hotel. The place itself is also charmingly unassuming but has some of the best accommodations in the area. The Guesthouse is an aparthotel with guests staying in one-, two-, and three-bedroom apartments with full kitchen facilities. Rooms: There are twenty-five apartments at the Guesthouse with the choice mainly just depending on the number of guests. The one-bedroom units can sleep up to four, the 1001 sq. ft. two bedrooms up to five, and the three-bedroom units up to seven with the help of a sofa bed. They are all broadly similar too – they mainly just differ in size – ranging from 601 sq. ft. to 1800 sq ft. The building used to be a luxury condo before its reincarnation as a boutique apart hotel and internally that’s pretty much what they are – luxury condos. Their design and decoration aren’t too dynamic, though they certainly have a touch of class and they are enormously comfortable, clean, and bright. All come with a balcony and modern apartment facilities such as cable TV, Nest thermostats, dishwashers, washing machines, and tumble dryers. Prices & Availability: Enter your dates and check prices at Booking.com here. Food & Facilities: There’s no restaurant or bar at The Guesthouse but they have an agreement with two excellent local restaurants to supply catered meals on order. Southport Grocery delivers breakfast which includes delicious pancakes and French toast, and lunch with a range of gourmet sandwiches, salads and soups. In the evening then Calo, a local Italian restaurant can deliver a whole host of classic Italian dishes including some really great thin-crust pizza. It being a hotel and not just an apartment block there are some cool social spaces. The roof terrace is a cool place to hang out, weather permitting, and it has lounge chairs and a barbecue. So too are the small, cozy Club Room and Library adjacent to the entrance lobby. There are two small boutique, informal stores by the lobby too, one selling locally made arts n crafts, jewelry, teeshirts, and more, the other READ MORE