Gay Chicago Chicago City Guide

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

Let’s start this gay Chicago travel guide with a roundup of the best places to stay in Chicago. An oh so very proper, British welcome is waiting for guests within The Langham, a glittering luxury hotel situated in a Mies van der Rohe-designed skyscraper overlooking the city and Lake Michigan. Up the posh ante at the Langham by upgrading to the hotel’s Club level where stunning views are served along with a buffet breakfast, afternoon tea and premium libations and where dedicated butlers make check in and check out a wholly civilized affair.

Once reserved for a privileged few, the Chicago Athletic Association – a mainstay of posh, mid-western elite for 122 years, has blissfully opened its doors to all. This downtown destination on the doorstep of Millennium Park is one of the city’s swankiest hotspots housed in a landmark building and ‘sporting’ everything from a rooftop bar to unique dining options and gaming rooms to elegant guest rooms replete with vintage athletic gear.

Where it sits tucked into its exclusive, Gold Coast neighbourhood; the Viceroy is a standout among a bevvy of neighbouring, historic mansions just steps from the Magnificent Mile and Lake Michigan. A celebration of locally-inspired luxury, the Viceroy melds cutting-edge luxury with ageless elegance across its 180 guestrooms and suites. Whether you’re staying the night or simply passing through, while at the Viceroy you’d be remiss not to have your martini shaken at Devereaux where breathtaking views and poolside plates are the perfect accoutrement to a cocktail and a decidedly chic way to help start your evening… or end your night.

Elegantly residential, The Thompson Hotel is tucked away in the toniest of the Gold Coast enclave; just minutes to the lakeshore and steps away from chic dining, theatre and the Lincoln Park Zoo. With newly designed interiors by Tara Bernerd, the Thompson is an elevated, mid-century-inspired beauty featuring spacious rooms and a drop-dead gorgeous, dual level penthouse loft that’s nothing less than sigh-worthy.