Beyond Boystown: A Perfectly Gay Weekend in Chicago

Maxime and I were giddy with excitement as we puttered on a petite ferry bound for Billy Bishop Airport on Toronto Island. After whisking our way through security we lounged on plush leather chairs, sipping hot tea and nibbling on those iconic (and addictive) Porter Airlines chocolate chip shortbread cookies.

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 as my partner in crime. We tackled the city over the course of three days via an itinerary which had been created to showcase my idea of an ultimate gay weekend in the Windy City: luxury hotel suites, top notch culinary creations, VIP architecture and art tours, rainbow dotted Boystown and the splish splash of summer fresh cocktails.

During our stay we divided time between two recently opened luxury hotels. The Langham Chicago opened in September 2013 and is located in the last office building designed by Mies van der Rohe, known for developing the modern skyscraper. The 316-room hotel resides within the 52-story landmarked riverfront property in the heart of downtown Chicago. The hotel lobby is uniquely located on the 2nd floor, a jaw dropping light-filled pavilion featuring an installation of Czechoslovakian glass blown pebbles which appear like hovering water droplets. Our spacious suite offered a stunning view of the Chicago River…

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 the neighbourhood stands out as one of the cities most prestigious neighbourhoods. Originally opened in 1988 as Hotel 21 East, the property was re-launched 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. Our corner suite featured a lovely white walled bathroom and plush king sized bed which offered amazing views of the city thanks to wrap around ceiling to floor windows.

Sips and Nibbles

My fondest memories of Chicago played out via fork, knife and spoon: dainty Afternoon Tea at The Langham’s Pavilion, Michelin Stars in your eyes at Moto, gay brunch at Wood, tasty tavern grub at State and Lake, brewpub love at Goose Island, Millennium Park bistro lunch at The Gage and Italian indulgence at Nico Osteria.

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 the LGBT community in Chicagoland. Originally founded in 1973 as Gay Horizons, the organization began as a volunteer-run meeting place for gays and lesbians and today offers three breezy floors which play host to a multitude of community events, theatre, youth outreach, education and therapy + health services. The lobby is connected to a Whole Foods (the gayest grocer in town) and the folks at the front desk have their fingers on the pulse of the LGBT Chicago community. Pop by to inquire about what queer 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 which specialize in tours to over 25 diverse neighbourhoods as well as over 40 special interests (art, architecture, food, local history etc…). We enjoyed a two hour walking tour of Boystown with Randy Plaisance who is an expert on Chicago’s famous architecture and LGBT community.

Best Bets for Bar Hopping

A visit to Chicago in the middle of hot-as-heat July will have you eager for a thirst quench. Luckily the city is packed with a plethora of opportunities to sip on stellar craft cocktails:

  1. Untitled: those looking to travel back in time to indulge in the speakeasy era can adventure on the nightly via the unmarked doors at 111 W Kinzie. Come experience intimate spaces and grand see-and-be-seen rooms. Prohibition era inspired French Potation (remy martin vsop, drambuie, luxardo maraschino, lemon, angostura, cava) packs a punch.
  2. 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 panorama’s. A 30-foot digital artwork lines the lounge while midcentury-inspired furniture recalls the era of classic cocktail culture. A perfect spot to grab a drink before indulging in Afternoon Tea service at the Pavilion. Opt to order The Madhattan Bar Cart Service (whiskey, carpano antica, benedictine, angostura bitters).
  3. Sidetrack: during the last 32 years, Sidetrack The Video Bar has grown to become Chicago’s most popular and famous gay bar. At the very heart of Boystown, Sidetrack now expands across six storefronts and features a courtyard, roof deck and bright and airy GlassBar. Must have Sidetrack sipper is the iconic grape flavoured gay drink slushy Ketel One Crush.
  4. Freestyle at the Dana Hotel: Freestyle lounge at the boutique Dana Hotel celebrates happy hour five nights a week and offers the perfect petite nook for people watching. Refresh your senses post massage via the Hibiskiss (absolut citron, hibiscus syrup, raspberry puree, soda).
  5. Roof on the WIT: If you’re looking to indulge in a dance-tastic Sunday gong show head to Roof at the WIT. As the elevator doors pop open you’ll be smacked in the face by EDM revellers who dance themselves silly al fresco while gazing over jaw dropping views of the city. The main stage regularly features top notch DJs from Vegas, Miami, LA and NYC which thump bass across the crowd as scantily clad dancers bump and hustle. The signature here is Sex on the Roof (absolut citron, st germain, aperol, orange, lemon).
  6. 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 which celebrates the European tradition of afternoon aperitifs and low-proof cocktails. Sweet seasonal sips can be found via Blueberry Cobbler (blueberry death’s door gin, citrus, honey, amaro cardamaro).

Massage Moment

The boutique Dana Hotel is located in downtown Chicago’s River North neighbourhood, know for hosting the largest concentration of art galleries in the United States outside of Manhattan. A visit to the hotels petite spa offers the perfect opportunity to rest and relax. Ranked #34 by Conde Nast Traveler’s Top 75 U.S. 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 of your aches and pains.

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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 history of Chicago 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 literally take days to shuffle and hustle through the collection. Beauty you just can’t miss: American Gothic by Grant Wood, Edward Hooper’s Nighthawks, Georges-Pierre Seurat’s A Sunday on 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 via 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 an adrenalin joy ride on Lake Michigan which 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 Tribune Tower, the Wrigley Building, Marina City, Trump Tower and the Willis (Sears) Tower.

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