Chicago’s so gay

I first met Maxime Bocken, a Toronto-based fashion photographer, two years ago over a plump frankfurter, a hoppy pale ale and crispy Belgian frites at Wvrst, in Toronto’s hip King Street West neighbourhood. Months later I’m happy to say this Belgian-born, always smiling photo nerd and I have become the best of friends. Max is a lover of architecture, design, fine art, good food and luxury living, so when I found out he had never been to Chicago, I insisted he join me on an upcoming trip as my partner in crime. We tackled the city over the course of three days via an itinerary that had been created to showcase my idea of an ultimate gay weekend in the Windy City.

We divided our stay between two recently opened luxury hotels. The Langham Chicago opened in September 2013 and is located in the last office building designed by Ludwig Mies van der Rohe, known for developing the modern skyscraper. The 316-room hotel resides within the 52-storey riverfront landmark in the heart of downtown Chicago. The hotel lobby, located on the second floor, is a jaw-dropping, light-filled pavilion featuring an installation of Czechoslovakian glass-blown pebbles that look like hovering water droplets.

If the Langham represents refined, opulent elegance, then the Thompson Chicago would be best described as urban sophistication meets contemporary chic. Located on the Gold Coast’s “Viagra Triangle,” one of the city’s most prestigious neighbourhoods, it opened in 1988 as Hotel 21 East and was relaunched in 1995 as the Sutton Place Hotel. Seventeen years later, the property underwent a complete rebirth, with an interior reimagined by acclaimed British designer Tara Bernerd.

A gay orientation
For years, the heart of Chicago’s gay community has been found in Boystown. If it’s your first visit to the city, head to Center on Halsted, the Midwest’s most comprehensive community centre, dedicated to securing the health and well-being of Chicago’s LGBT community. Founded in 1973, the organization began as a volunteer-run meeting place for gays and lesbians called Gay Horizons and today offers three breezy floors that play host to a multitude of community events, theatre, youth outreach, education and therapy and health services. The lobby is connected to a Whole Foods store (the gayest grocer in town), and the folks at the front desk have their fingers on the pulse of the queer community. Pop by to inquire about what parties you simply can’t miss while in town.

If you like to plan your adventures in advance, be sure to check out Chicago Greeter. The free service offers friendly, knowledgeable local guides who specialize in tours to more than 25 diverse neighbourhoods and more than 40 special interests (art, architecture, food, local history, et cetera). We enjoyed a two-hour walking tour of Boystown with Randy Plaisance, who is an expert on Chicago’s architecture and LGBT community.

Best bets for bar hopping
All that walking will leave you eager for a thirst quencher. Luckily, the city is packed with a plethora of opportunities to sip on stellar craft cocktails:

Untitled: Those looking to travel back in time to the speakeasy era can indulge nightly via the unmarked doors at 111 W Kinzie St. Come experience intimate spaces and grand see-and-be-seen rooms. The Prohibition-era-inspired French Potation (Rémy Martin brandy, Drambuie, Luxardo Maraschino, lemon, Angostura bitters and cava) packs a punch.

Travelle at The Langham: Enjoy a stiff drink at The Langham’s art-infused bar and lounge. Sip yourself silly while overlooking the Chicago River and take in one of the city’s best skyline panoramas. A 30-foot digital artwork lines the lounge while mid-century-inspired furniture recalls the era of classic cocktail culture. This is a perfect spot to grab a drink before indulging in afternoon tea service at the Pavilion. Opt for the Madhattan Bar Cart Service (whiskey, Carpano Antica vermouth, Benedictine liqueur and Angostura bitters).

Sidetrack: During the last 32 years, Sidetrack video bar has grown to become Chicago’s most popular and famous gay bar. At the very heart of Boystown, Sidetrack now stretches across six storefronts and features a courtyard, roof deck and the bright and airy GlassBar. Sidetrack’s must-have sipper is the iconic grape-flavoured Ketel One Crush slushy.

Salone Nico at the Thompson: Located in an intimate space behind the main staircase at the always-trending Thompson Hotel, Salone Nico is a welcoming gathering space that celebrates the European tradition of afternoon aperitifs and low-proof cocktails. Sweet seasonal sips can be found via the Blueberry Cobbler (blueberry Death’s Door gin, citrus, honey and Cardamaro amaro).

Your massage moment
The boutique Dana Hotel is located in downtown Chicago’s River North neighbourhood, known for hosting the largest concentration of art galleries in the United States outside Manhattan. A visit to the hotel’s petite spa offers the perfect opportunity to rest and relax. Ranked 34th on Condé Nast Traveler’s Top 75 US Hotel Spas in 2013, the menu here is composed of natural and therapeutic services. Wrap yourself in a plush white robe and sip a cup of herbal tea in the relaxation lounge before snoozing through the afternoon while a skilled massage therapist smoothes out all your aches and pains.

That fine art
The Art Institute of Chicago was founded as both a museum and school for the fine arts in 1879, a critical era in the city’s history as civic energies were devoted to rebuilding the metropolis that had been destroyed by the Great Fire of 1871. The permanent collection features nearly 300,000 works of art in fields ranging from Chinese bronzes to contemporary design and from textiles to installation art. Today the museum is recognized internationally as one of America’s leading art institutions. The museum is so vast it would take days to shuffle and hustle through the collection, but this beauty you just can’t miss: Grant Wood’s American Gothic, Edward Hopper’s Nighthawks, Georges-Pierre Seurat’s A Sunday on the Island of La Grande Jatte, Claude Monet’s Paris Street; Rainy Day and Pablo Picasso’s The Old Guitarist.

Skyscraper cruising
The most memorable way to explore the Windy City is via an architectural tour along the Chicago River. Max and I hopped on the Seadog for a 75-minute journey, which departs several times a day from Navy Pier. The trip starts with a joy ride on Lake Michigan that offers stunning panoramic views of the city skyline. The remainder of your aqua adventure is a gentle stroll up the city’s iconic river, which allows guests to gaze up at dozens of world-renowned buildings, including the Tribune Tower, the Wrigley Building, Marina City, the Trump Tower and the Willis (Sears) Tower.

For the most up-to-date travel information on gay Chicago see our City Guide, Listings Guide, Events Guide and Activities Guide.