Go local in the groovy, diverse North Side neighbourhood of Andersonville, with your own swanky apartment at the Guesthouse Hotel Chicago. This charming place to stay will put you within steps of a unique tapestry of inclusive, independent dining, design, tippling and lifestyle businesses.
It’s hard to think of a vibey, hospitality-rich neighbourhood more harmoniously diverse than Chicago’s northern inner-burb Andersonville. Once the centre of the city’s Swedish community, whose roots are still represented in landmarks like the Swedish American Museum and the Viking-kitsch 1934 dive bar Simon’s, the area had for a chunk of the 1980s and 1990s the distinction of being the city’s lesbian epicentre, before settling into the affluent, shopping-focused rainbow gentrification that defines it today. Allies may now outnumber radical queer community-builders here, but the inclusivity characterised by large numbers of LGBTQ-owned businesses among the cool boutiques, bijou restaurants and creative coffee shops that line its handsome Americana main drag still feels like a warm bath for the diverse visitor.
So we loved the chance to pretend to live in this eminently walkable part of the city – handy also for the happening adjacent hoods Uptown, Lincoln Park and Ravenswood – with our own smart, spacious and well-located apartment to explore from, courtesy of the stylish Guesthouse Hotel Chicago, opened in 2014 and the only hotel in the immediate vicinity. On a rare quiet(ish) block on Andersonville’s buzzing lifestyle artery Clark Street, one-, two- and three-bedroom units are all sparingly but stylishly decorated to make the most of the abundant natural light and space (these high-ceilinged units were originally purpose-built as luxury condos) with wooden floors, richly coloured vintage rugs and furnishings that nod to mid-century modern. It’s worth knowing, too, that the owners have recently opened a second property based on a similar neighbourhood concept in Austin, Texas, the 80-suite Colton House Hotel.
In the four-storey, red-brick boutique hotel’s 25 apartments, bedrooms and beds are large and the capacious, well-organised storage space lets you nest in quickly and feel right at home. This is also very handy for multiple drop-offs if, as ours were, your head is turned by the amazing local shopping for fashion, homewares and art. Living spaces are generous and feature fully fitted-out kitchens with granite islands which double as dining spaces (strictly an aparthotel, the Guesthouse has no on-site restaurant), and, in the three-bedroom and two-bedroom deluxe suites, cosy gas fireplaces. Each apartment comes with a gleaming white bathroom with toiletries by Oprah-endorsed, LGBTQ-owned brand Beekman 1802, cute patio balconies with furniture and gas-fired barbecue grills, a washing machine and tumble dryer and access to garage parking. Several of the apartments are adapted for accessibility.
| Perfect for | Fly into | Right on time |
| The Insider | ORD | GMT -6 |
| While you’re Out There |
| We’ll be honest. Our Chicago pals’ recommendation that we spend our Friday evening at Chicago Magic Lounge didn’t fill us with joyous anticipation, but boy, did this bawdy, bad-ass spot change our minds. Channelling Prohibition speakeasies with its disguised-as-a-laundromat entrance and velvet-draped stage set, the seven-year-old venue taps into both Chicago’s history as a Capone-era ‘bar magic’ hub and the neighbourhood’s progressiveness with front-of-house staff specifically recruited to reflect Andersonville’s inclusivity, a wildly diverse roster of mind-blowing magic talent, racy, pacy programming and friendly, up-for-it audiences. Daft, different, decadent and brilliant. |
Communal spaces for a change of scene include a large, daylight-flooded lobby lounge with a warehouse-meets-trendy-antiquerie aesthetic. Its industrial-chic bones – polished concrete floor, statement features in reclaimed timber – are nicely warmed by an eclectic art collection, gently kitsch crystal chandelier and big fireside chesterfield sofas that entice you to curl up with a book from the dapper adjacent library. There’s a cute roof deck, too, open seasonally, with great views of downtown from comfy outdoor sofas beneath a fairy-light-fringed pergola, and a small fitness room with state-of-the-art cardio machines and yoga mats.
The efforts of the Guesthouse Hotel Chicago to support other local businesses chime perfectly with the neighbourhood’s creative, indie vibe, for example, in the micro-mart at reception where you can buy from a curated selection of locally made jewellery, crafts, gifts and gourmet snacks and drinks (including great local craft beers). And the super friendly 24/7 front-of-house staff have all the best tips for your every Andersonville dining, tippling or shopping whim. They can also arrange in-room spa treatments from trusted partners or book you in at the next-door Revive Massage Therapy and Spa. Breakfast in bed will be delivered from the stylish local Southport Grocery and Café and excellent thin-crust pizza from Italian restaurant Calo.
Photography courtesy of The Guesthouse Hotel Chicago
