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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.Must have Sidetrack sipper is the iconic grape flavoured gay drink slushy Ketel One Crush. At the very heart of Boystown, Sidetrack now expands across six storefronts and features a courtyard, roof deck and bright and airy GlassBar. Sidetrack: during the last 32 years, Sidetrack The Video Bar has grown to become Chicago’s most popular and famous gay bar.Opt to order The Madhattan Bar Cart Service (whiskey, carpano antica, benedictine, angostura bitters). A perfect spot to grab a drink before indulging in Afternoon Tea service at the Pavilion. A 30-foot digital artwork lines the lounge while midcentury-inspired furniture recalls the era of classic cocktail culture. Sip yourself silly while overlooking the Chicago River and take in one of the city’s best skyline panorama’s. Travelle at The Langham: enjoy a stiff drink at The Langham’s art infused bar and lounge.Prohibition era inspired French Potation (remy martin vsop, drambuie, luxardo maraschino, lemon, angostura, cava) packs a punch. Come experience intimate spaces and grand see-and-be-seen rooms. 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.Luckily the city is packed with a plethora of opportunities to sip on stellar craft cocktails: Best Bets for Bar HoppingĪ visit to Chicago in the middle of hot-as-heat July will have you eager for a thirst quench. We enjoyed a two hour walking tour of Boystown with Randy Plaisance who is an expert on Chicago’s famous architecture and LGBT community. 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…). If you like to plan your adventures in advance be sure to check out Chicago Greeter. Pop by to inquire about what queer parties you simply can’t miss while in town. 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.
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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. 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. A Gay Orientationįor years the heart of Chicago’s gay community has been found in Boystown. 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. Our spacious suite offered a stunning view of the Chicago River… 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. The 316-room hotel resides within the 52-story landmarked riverfront property in the heart of downtown Chicago. 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. 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.ĭuring our stay we divided time between two recently opened luxury hotels. 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. Maxime and I were giddy with excitement as we puttered on a petite ferry bound for Billy Bishop Airport on Toronto Island.