Gay Chicago Chicago City Guide

Curation by Yasmina Rodríguez, words by Gina Samarotto

A friendly bunch of craft beer brewers living across a city of 77 neighbourhoods crammed with cutting-edge architecture, world-class cuisine and classy Lake Michigan shores, the people of Chicago really could be more smug. Circumnavigate the vibrant Loop of downtown Chicago or walk straight along the affluent Gold Coast to discover just what the locals are keeping humble about; as well as swanky retail revelry on all sides, you’ll discover a chilled out bar culture and a nightlife scene to remember, particularly for LGBT partygoers. With a solid reputation as one of the most inclusive LGBTQ+ communities in the US, Chicago is a city for all. Boystown, in particular, with its fine array of after-hours entertainment, decadent spas and boutiques, not to mention the upcoming Andersonville, famed for its Swedish Heritage and gay-friendly atmosphere. Whether it’s a Pride Parade, Dyke March or any other summer street festival you’re after, Chicago can satisfy your hedonistic cravings (as well as those for definitive Deep Dish Pizza). Read on for more of what to do in Chicago, with Mr Hudson’s trusty Chicago gay travel guide.

The best hotels in Chicago

Chicago’s most distinguished address is arguably The Langham, ensconced within the final skyscraper designed by Ludwig Mies van der Rohe at 330 North Wabash Avenue. Set in vibrant River North with sweeping views of the Chicago River and the glittering skyline beyond, the property delivers 316 rooms and suites with floor-to-ceiling windows, deep soaking tubs and bedding of an almost indecent softness. The Club Lounge — where attentive butlers know your name before you’ve finished your morning espresso — adds breakfast, afternoon tea and premium libations; whilst the Chuan Spa, drawing on Traditional Chinese Medicine principles and a 67-foot indoor pool, provides one of the most restorative wellness programmes in the city. For those wanting proximity to everything without sacrificing a single thread count, the Langham is the obvious choice.

A rather different character awaits at the Chicago Athletic Association, occupying an 1890s Venetian Gothic landmark on Michigan Avenue, directly opposite Millennium Park. Reimagined by design firm Roman and Williams, the 240-room hotel threads contemporary comfort through a framework of athletic nostalgia — aged leather, warm timber and vintage sporting paraphernalia. Cindy’s rooftop bar, perched beneath a glass atrium on the 13th floor with sweeping views of Cloud Gate and the lake, is reason alone for a visit.

For those whose hearts belong to the Gold Coast, the Viceroy Chicago is an architectural triumph. Behind a preserved 1920s terra cotta facade sits a property of genuine mid-century chic: gilded headboards, black and gold accents, and 180 immaculate rooms and suites. The rooftop lounge, Pandan, serves East Asian-inspired cocktails with panoramic city views and is a seasonal essential. Moments from the Magnificent Mile and the shores of Lake Michigan, the Viceroy is the ideal base for those with one eye on the boutiques of Oak Street and the other on the horizon.